Hiii

 ‫א‬‫א‬‫א‬
ã¹]<gè…‚jÖ]æ<ËÖ]<Üé×Ãj×Ö<íÚ^ÃÖ]<í‰‰ö¹]
‫א‬‫א‬‫א‬‫א‬
‫א‬
‫א‬‫א‬
١٤٠
 ‫א‬  ١٤٠  ‫א‬
  ‫א‬‫א‬ ‫א‬
 W،،‫א‬‫א‬،‫א‬

‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬
  ‫א‬ ‫א‬  ،‫א‬   ‫א‬ ‫א‬ ‫א‬ ‫א‬ ‫א‬ 
‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬
W‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬
 K ‫א‬‫א‬‫א‬

‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬
  ‫א‬        ،‫א‬ ‫א‬‫א‬  
‫א‬  ‫א‬ ‫א‬ ‫א‬ ‫א‬ ‫א‬   ‫א‬    ،  
‫א‬،‫א‬‫א‬‫א‬‫א‬
‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬
     ‫א‬  ‫א‬   ،‫א‬   
 K‫א‬‫א‬،‫א‬‫א‬

‫א‬  ?  ? ‫א‬ ‫א‬  ? ‫א‬ ‫א‬  
 K‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬?

‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬
،‫א‬،‫א‬‫א‬‫א‬‫א‬
 K‫א‬‫א‬‫א‬‫א‬‫א‬

   W    ‫א‬ ‫א‬  ‫א‬    ‫א‬
 K‫א‬

 ‫א‬‫א‬‫א‬‫א‬      
   ١٤٠  ‫א‬
  ‫א‬‫א‬ ‫א‬
‫א‬،KK‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬
، ‫א‬‫א‬
 ‫א‬‫א‬‫א‬
‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬
‫א‬‫א‬،‫א‬‫א‬‫א‬‫א‬‫א‬
‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬
‫א‬‫א‬‫א‬،‫א‬،‫א‬‫א‬‫א‬‫א‬‫א‬
‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬
–‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬
‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬–‫א‬‫א‬
‫א‬‫א‬K‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬
K‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬،،‫א‬
‫א‬‫א‬‫א‬ ،‫א‬‫א‬‫א‬
‫א‬،‫א‬‫א‬‫א‬‫א‬K
‫א‬‫א‬‫א‬‫א‬،‫א‬
 K‫א‬
‫א‬‫א‬‫א‬‫א‬‫א‬
  ‫א‬‫א‬‫א‬
K‫א‬‫א‬‫א‬،‫א‬‫א‬
K‫א‬‫א‬‫א‬‫א‬،‫א‬
 ‫א‬‫א‬‫א‬
‫א‬‫א‬‫א‬‫א‬
‫א‬‫א‬

 
١
 ‫א‬‫א‬  ١٤٠  ‫א‬
   ‫א‬‫א‬ ‫א‬
 W‫א‬‫א‬
،‫א‬‫א‬،‫א‬‫א‬،‫א‬‫א‬‫א‬‫א‬
 K‫א‬‫א‬‫א‬
 W‫א‬‫א‬
 W‫א‬‫א‬‫א‬
 K‫א‬‫א‬‫א‬‫א‬‫א‬ -١
K‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬ -٢
 W‫א‬‫א‬‫א‬
 K٪٨٠‫א‬‫א‬‫א‬
 W‫א‬‫א‬
 K‫א‬
 W‫א‬‫א‬
 KOverhead Projector
K‫א‬‫א‬
 W‫א‬‫א‬
 K‫א‬‫א‬‫א‬‫א‬
-١-
 ‫א‬‫א‬  ١٤٠  ‫א‬
   ‫א‬‫א‬ ‫א‬
 W١J ١
K‫א‬‫א‬‫א‬‫א‬
‫א‬‫א‬‫א‬Organic
 ،،‫א‬‫א‬،‫א‬
‫א‬،‫א‬،‫א‬‫א‬‫א‬K‫א‬

 ‫א‬1828 Wohler‫א‬‫א‬‫א‬‫א‬K‫א‬
‫א‬‫א‬E‫א‬F‫א‬
 W‫א‬‫א‬،

O
 NH4OCN H2N C NH2


‫א‬‫א‬‫א‬،‫א‬،‫א‬
 K‫א‬،
‫א‬‫א‬،‫א‬‫א‬‫א‬‫א‬
‫א‬‫א‬‫א‬‫א‬ K‫א‬‫א‬‫א‬
‫א‬ ‫א‬‫א‬‫א‬K
 K‫א‬‫א‬‫א‬‫א‬
‫א‬‫א‬‫א‬ ‫א‬‫א‬‫א‬
،‫א‬‫א‬‫א‬‫א‬ K ‫א‬
‫א‬،‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬
‫א‬‫א‬،‫א‬‫א‬‫א‬،‫א‬‫א‬‫א‬
،‫א‬‫א‬‫א‬‫א‬،‫א‬‫א‬‫א‬
 K‫א‬‫א‬،‫א‬‫א‬‫א‬‫א‬،‫א‬‫א‬‫א‬
‫א‬‫א‬‫א‬‫א‬ ‫א‬‫א‬‫א‬‫א‬
 K‫א‬
-٢-
 ‫א‬‫א‬  ١٤٠  ‫א‬
   ‫א‬‫א‬ ‫א‬
‫א‬،‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬
‫א‬‫א‬K‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬
‫א‬‫א‬‫א‬،‫א‬‫א‬KFunctional Groups   ‫א‬‫א‬
‫א‬‫א‬‫א‬
 ‫א‬‫א‬‫א‬،‫א‬
E–OHF ‫א‬،‫א‬‫א‬‫א‬‫א‬‫א‬K
‫א‬‫א‬Ksp3‫א‬
‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬،‫א‬‫א‬‫א‬
 K‫א‬‫א‬‫א‬‫א‬،‫א‬

 WFunctional Group ‫א‬‫א‬١J ٢

‫א‬‫א‬‫א‬‫א‬‫א‬ 
،،‫א‬ ‫א‬K‫א‬‫א‬ ‫א‬
O
‫א‬‫א‬‫א‬‫א‬K‫א‬‫א‬‫א‬ C H
 W‫א‬‫א‬‫א‬‫א‬

O
[O]
O CH3C-OH ( ‫) ﺣﻤﺾ آﺮﺑﻮآﺴﻴﻠﻲ‬
CH3C H
[H]
CH3CH 2OH ( ‫) ﻏﻮل‬
 ‫أ‬ 

[O]
O CH3CH2COOH ( ‫) ﺣﻤﺾ آﺮﺑﻮآﺴﻴﻠﻲ‬
CH3 CH2C H
[H]
CH3CH2CH2OH ( ‫) آﺤﻮل‬
 ‫ب‬

-٣-
 ‫א‬‫א‬  ١٤٠  ‫א‬
   ‫א‬‫א‬ ‫א‬
[O]
O CH3CH2CH2COOH ( ‫) ﺣﻤﺾ آﺮﺑﻮآﺴﻴﻠﻲ‬
CH3CH2CH2C H
[H]
CH3CH2CH2CH2OH ( ‫) آﺤﻮل‬
‫ج‬
  

‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬
‫ ( א‬-CHO) ‫א‬‫א‬‫א‬
،‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬K‫א‬‫א‬
‫א‬‫א‬K‫א‬‫א‬‫א‬
 
،‫א‬‫א‬
K‫א‬‫א‬‫א‬‫א‬‫א‬
 K‫א‬‫א‬E١J ١F
 ‫א‬‫א‬WE١J ١F
 ‫א‬  ‫א‬‫א‬
 
 ‫א‬‫א‬  ‫א‬
 ‫א‬
 H2C CH2 C= C

 ‫א‬‫א‬
 E‫א‬‫א‬F
 
 ‫א‬ C C
 H C C H 
X
Br
 ‫א‬‫א‬‫א‬ C
CH3I ,

 ( X = I, Br, Cl , F )
 ‫א‬
 CH3CH 2OH C OH

-٤-
 ‫א‬‫א‬  ١٤٠  ‫א‬
   ‫א‬‫א‬ ‫א‬
 ‫א‬‫א‬ O C
 CH3 O CH3 C

O O
 ‫א‬‫א‬
 CH3 C H  C H
O O
 ‫א‬
C C C
 CH3 C CH3 
O O
‫א‬‫א‬
 H C OH  C OH
‫א‬ O
O
 ‫א‬ C Y
 CH3 C OCH 3 ( Y = Cl ,OR, NR 2 ,...)
CH3
 ‫א‬ C N
 CH3NH2 , CH3NH 
 ‫א‬
 CH3CN C C N

NO 2 O
CH 3NO 2 ,  
C N O-

 ‫א‬ C SH
 CH3SH

 W‫א‬‫א‬‫א‬١J ٣
K‫א‬‫א‬EF‫א‬‫א‬‫א‬‫א‬ 
‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬
‫א‬‫א‬?hemolytic?‫א‬K‫א‬
K‫א‬‫א‬
 ‫א‬?heterolytic?،
 K X‫א‬‫א‬‫א‬‫א‬‫א‬

-٥-
 ‫א‬‫א‬  ١٤٠  ‫א‬
   ‫א‬‫א‬ ‫א‬
.
C . .X C. + X " ‫" أﻧﻔﺼﺎم ﻣﺘﺠﺎﻧﺲ‬
 ‫ﺟﺬر ﺣﺮ‬


_
}
C . .X C + + .. X
‫أﻳﻮن آﺮﺑﻮﻧﻴﻮم‬
carbonium ion
" ‫" اﻧﻔﺼﺎم ﻏﻴﺮ ﻣﺘﺠﺎﻧﺲ‬
_
C . .X C .. + X +
‫أﻳﻮن آﺮﺑﺎﻧﻴﻮن‬
 carbanion

 ‫א‬K،‫א‬‫א‬‫א‬
‫א‬K‫א‬‫א‬‫א‬‫א‬‫א‬ ‫א‬‫א‬
 K‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬
X‫א‬،‫א‬‫א‬‫א‬‫א‬
K‫א‬،‫א‬  
‫א‬‫א‬ ‫א‬‫א‬‫א‬
K‫א‬‫א‬X‫א‬E‫א‬F‫א‬‫א‬
KX‫א‬‫א‬‫א‬‫א‬E‫א‬F‫א‬‫א‬
K‫א‬‫א‬‫א‬‫א‬‫א‬
‫א‬‫א‬‫א‬‫א‬
 ‫א‬‫א‬‫א‬
‫א‬‫א‬‫א‬K‫א‬‫א‬‫א‬‫א‬‫א‬

 ‫א‬، E‫א‬F‫א‬
K‫א‬‫א‬NucleophilesENu-F‫א‬ElectrophilesEE+F
F‫א‬‫א‬‫א‬‫א‬‫א‬ ‫א‬
  ‫א‬
 WK‫א‬E‫א‬
-٦-
 ‫א‬‫א‬  ١٤٠  ‫א‬
   ‫א‬‫א‬ ‫א‬
H+ , Br+ , NO2+ , BF3 , AlCl3


F‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬
 WKE

. ._. . . _. . ._ . ._ ..
HO . , RO . , RS .. , CN .. , H2O .. , R2N ..
 .. .. ..
 

‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬
 W،‫א‬
‫א‬،substitution‫א‬‫א‬‫א‬ J ١
K‫א‬
 CH 3CH2OH + HBr CH3CH2Br +H2O

 E‫א‬‫א‬F
‫א‬‫א‬‫א‬Waddition‫א‬ J ٢
K  ‫א‬‫א‬‫א‬‫א‬‫א‬
 CH2 CH2 + Br2 CH2BrCH 2Br

 EF
‫א‬،eliminationE‫א‬F‫א‬‫א‬ J ٣
‫א‬‫א‬F ‫א‬‫א‬‫א‬‫א‬
 KE

 CH3CH2Br + NaOH CH 2 CH2 + H2O + NaBr
 E‫א‬‫א‬F

-٧-
 ‫א‬‫א‬  ١٤٠  ‫א‬
   ‫א‬‫א‬ ‫א‬
 
 W‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬W١

CH2OH
_
‫ب‬ O
‫ ح‬- O
  CH 3C N(CH 3)2 ‫أ‬

CH3
_ _ CH3 Pb CH3 ‫د‬
 CH3CH 2F ‫و‬ ‫هـ‬
 CH3

O
 
CH 3OCH 2CH 2C H ‫ج‬


 ‫؟‬‫א‬،‫א‬‫א‬‫א‬W٢

+ - -
 CH3CH2 , ZnCl2 , F , CH3CH2 , CH3OH , CH3SH , CH3NH2

W‫א‬‫א‬W٣
O
a) - CH3 C H + CH3MgI CH3CHCH3
OMgI
b) - CH3CH2I + NaSH CH3CH2SH + NaI

c) - CH2 CH CH3 + HCl CH3CHCH 3
Cl
-٨-
 ‫א‬‫א‬  ١٤٠  ‫א‬
   ‫א‬‫א‬ ‫א‬
 ١J ٤‫א‬‫א‬
 W١
 J J J J ‫א‬

 W٢
 K‫א‬‫א‬WCH3NH2
 K‫א‬WCH3OH
 KWF-
 KW ZnCl2

 K‫א‬‫א‬‫א‬‫א‬W٣
 K‫א‬‫א‬

-٩-
 ‫א‬‫א‬‫א‬
‫א‬‫א‬‫א‬‫א‬
‫א‬‫א‬
‫א‬‫א‬
 ‫א‬‫א‬
٢
 ‫א‬‫א‬  ١٤٠  ‫א‬
‫א‬‫א‬  ‫א‬‫א‬ ‫א‬
 W‫א‬‫א‬
‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬
 K‫א‬‫א‬‫א‬‫א‬‫א‬
 W‫א‬‫א‬
 J W‫א‬‫א‬‫א‬
 K‫א‬‫א‬ .١
K‫א‬‫א‬‫א‬ .٢
،E،،F‫א‬‫א‬‫א‬ ‫ א‬.٣
K‫א‬‫א‬
 W‫א‬‫א‬‫א‬
 K٪٨٥‫א‬‫א‬‫א‬
 W‫א‬‫א‬
 K٨
 W‫א‬‫א‬
 KOverhead Projector .١
K‫א‬‫א‬ .٢
K‫א‬‫א‬‫א‬‫א‬‫א‬ .٣
K .٤
 W‫א‬‫א‬
 K‫א‬‫א‬‫א‬‫א‬
- ١٠ -
 ‫א‬‫א‬  ١٤٠  ‫א‬
‫א‬‫א‬  ‫א‬‫א‬ ‫א‬
 ‫א‬٢J ١
 ‫א‬‫א‬
 W
 W‫א‬J 
‫א‬‫א‬‫א‬
‫א‬K‫א‬‫א‬–‫א‬‫א‬،
 W
 ‫א‬،saturated‫א‬‫ א‬K
–
 Ethane CH3-CH3alkanes‫א‬
،J ‫א‬،unsaturated‫ א‬K
W
،EC=CF–‫א‬‫א‬،alkenes‫ א‬J ١
،EC C F–‫א‬‫א‬alkynes ‫א‬
‫א‬‫א‬‫א‬،‫א‬
 ‫א‬‫א‬
 K
،‫א‬Aromatic Hydrocarbons‫א‬‫א‬‫ א‬J ٢
 K C10H8‫א‬‫א‬‫א‬
 WAlkanes‫א‬٢J ٢
،‫א‬‫א‬‫א‬،‫א‬
‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬،‫א‬‫א‬‫א‬
 K‫א‬‫א‬‫א‬،‫א‬‫א‬‫א‬
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 ‫א‬‫א‬  ١٤٠  ‫א‬
‫א‬‫א‬  ‫א‬‫א‬ ‫א‬
 ‫א‬‫א‬‫א‬
nCnH2n+2W‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬ 
‫א‬‫א‬K‫א‬‫א‬EnFEKKKKKKK،٤{٣{٢{١=nF
 ‫א‬،‫א‬، ‫א‬
 K‫א‬
 W‫א‬٢J ٢J ١
‫א‬‫א‬‫א‬،E-aneF‫א‬‫א‬  
E-aneF‫א‬‫א‬E ‫א‬F‫א‬‫א‬ 
 E١J ٢F،
 ‫א‬E١J ٢F
n  ‫א‬‫א‬ ‫א‬

1 methane   CH4
2 ethane   CH3CH3 
3 propane   CH3CH2CH3 
4 butane    CH3CH2CH2CH3
5 pentane   CH3(CH2)3CH3
6 hexane   CH3(CH2)4CH3
7 heptane   CH3(CH2)5CH3
8 octane   CH3(CH2)6CH3 
9 nonane   CH3(CH2)7CH3
10 decane   CH3(CH2)8CH3 

- ١٢ -
 ‫א‬‫א‬  ١٤٠  ‫א‬
‫א‬‫א‬  ‫א‬‫א‬ ‫א‬
CH2‫א‬‫א‬‫א‬‫א‬
 ‫א‬‫א‬،Methylene‫א‬
 W‫א‬‫א‬


 Butane C4H8W‫א‬‫א‬
CH3 CH CH3
 CH3-CH2-CH2-CH3
 n-Butane  CH3
 IsobutaneJ 
 Pentane C5H12 W‫א‬‫א‬


 CH 3
CH3 CH CH2 CH3 CH3CH2CH2CH2CH3
CH 3 C CH3

CH3 
 CH 3
 J 
 –  – Neopentane
Isopentane N-pentane
 WAlkyl Group ER-F‫א‬

‫א‬‫א‬ER-F‫א‬
‫א‬ ‫א‬،methylCH3-‫א‬
‫א‬‫א‬‫א‬‫א‬E 2-2F‫א‬KEthylECH3CH2-F‫א‬
 ‫א‬‫א‬
- ١٣ -
 ‫א‬‫א‬  ١٤٠  ‫א‬
‫א‬‫א‬  ‫א‬‫א‬ ‫א‬
 K‫א‬‫א‬١٠J ٢‫א‬
‫א‬‫א‬
 ‫א‬‫א‬  ‫א‬
 ‫א‬
 Methyl  CH3J  MethaneCH4
 Ethyl  CH3CH2- Ethane CH3CH3
Propane
N-Propyl  CH3CH2CH2-
 CH3CH2CH3

Isopropyl   CH3-CH-CH3  CH3CH2CH2CH3
n-Butyl  CH3CH2CH2CH2-
sec- Butyl  CH3CHCH2CH3  n-Butane 
CH3
 Isobutyl _
  CH 3 CH CH 2
 CH3
   CH3 CH CH3
  
Tert-butyl CH3  Isobutane
 CH3 C 
  CH3

Cycloalkanes ‫א‬‫א‬
 W‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬
CH 2
 CH 2 CH 2
  Cyclopropane
 

   
- ١٤ -
 ‫א‬‫א‬  ١٤٠  ‫א‬
‫א‬‫א‬  ‫א‬‫א‬ ‫א‬
CH2 CH2
  CH 2 CH2
  
  Cyclobutane
  
  CH2
CH2 CH2
CH2 CH2
 
 Cyclopentane
 

CH2CH3
 
 Ethylcyclopropane
 WIUPAC‫א‬‫א‬‫א‬
‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬ 
 IUPAC W‫א‬‫א‬،‫א‬‫א‬
International Union of Pure and Applied Chemistry.
W‫א‬‫א‬
E‫א‬F‫א‬‫א‬‫א‬‫א‬ E١
 K‫א‬‫א‬‫א‬‫א‬
‫א‬‫א‬
 ‫א‬‫א‬‫א‬‫א‬‫א‬ E٢
‫א‬‫א‬‫א‬‫א‬‫א‬ ‫א‬K‫א‬‫א‬‫א‬
،‫א‬‫א‬‫א‬‫א‬E‫א‬F‫א‬‫א‬ EJ F
‫א‬ ‫א‬‫א‬ane‫א‬
W‫א‬‫א‬yl
 
- ١٥ -
 ‫א‬‫א‬  ١٤٠  ‫א‬
‫א‬‫א‬  ‫א‬‫א‬ ‫א‬
1 2 3 4 5 6
CH 3CH 2 CHCH 2CH 2 CH 3
 CH 2CH 3
 
 3-Ethylhexane
E‫א‬‫א‬
 F‫א‬‫א‬‫א‬‫א‬‫א‬ 
‫א‬penta ،tetra،tri،di‫א‬،‫א‬‫א‬‫א‬
‫א‬‫א‬ KKKKKK،،
 ‫א‬‫א‬‫א‬
‫א‬‫א‬‫א‬‫א‬،
 W‫א‬‫א‬‫א‬

CH3
CH3 CH CH2 C CH
5 43 3 2 1
 CH3 CH3

2-2-4-Trimethylpentane
‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬  
 W‫א‬‫א‬
 
CH2CH3
8 7 6 5 4 3 2 1
CH3 CH2 CH2 CH CH C CH2 CH3
_
 CH3 CH2 CH2 CH3 CH2CH3

 3,3-Diethyl-4-methyl-5-n-propyloctane
 
‫א‬‫א‬‫א‬  
 W‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬

7 6 5 4 3 2 1
CH 3 CH 2 CH CH 2 CH CH 2 CH 3
 CH 3 CH 2CH 3
- ١٦ -
 ‫א‬‫א‬  ١٤٠  ‫א‬
‫א‬‫א‬  ‫א‬‫א‬ ‫א‬

3-Ethyl-5-Methylheptane

 ‫א‬‫א‬E‫א‬F‫א‬‫א‬ 
،EaneF‫א‬EylF‫א‬،‫א‬
‫א‬ ‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬
‫א‬
 ‫א‬‫א‬‫א‬‫א‬‫א‬
 W‫א‬
CH3 CH3
1' 2' _
3 CH CH CH3
CH3 CH2 CH CH CH2 CH2 CH2 CH3
1 2 4 5 6 7 8
CH2 CH2CH3
 CH3

 3-Ethyl-4(1',2',Dimethylpropyl) nonane

E‫א‬F‫א‬‫א‬‫א‬
 ‫א‬‫א‬‫א‬‫א‬
‫א‬‫א‬‫א‬‫א‬K‫א‬‫א‬‫א‬
 W‫א‬E‫א‬
F: Fluoro NO2W Nitro
 ClW Chloro NH2W Amino
BrW Bromo CNW Cyano
 IW Iodo  
- ١٧ -
 ‫א‬‫א‬  ١٤٠  ‫א‬
‫א‬‫א‬  ‫א‬‫א‬ ‫א‬
W
Br
5 4 2 1
CH3CHCHCH 2CH3
3
CH3 Cl
 3-Bromo-2-chloro-4-methylpentane

‫א‬ ‫א‬‫א‬‫א‬‫א‬‫א‬
،‫א‬‫א‬‫א‬‫א‬‫א‬neo-‫א‬iso-
‫א‬‫א‬tridisec-tert-‫א‬‫א‬‫א‬
 K‫א‬
 W‫א‬‫א‬‫א‬‫א‬٢J ٢J ٢
‫א‬،nonpolar‫א‬ 
‫א‬،‫א‬‫א‬‫א‬‫א‬C4C1،‫א‬‫א‬
١٨‫א‬‫א‬‫א‬‫א‬، C17C5
،‫א‬ ‫א‬،‫א‬‫א‬ K‫א‬‫א‬
‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬،‫א‬‫א‬
‫א‬‫א‬ ،‫א‬‫א‬‫א‬E‫א‬‫א‬F‫א‬
 K‫א‬
 W‫א‬‫א‬‫א‬٢J ٢J ٣
‫א‬‫א‬،‫א‬‫א‬
 W‫א‬‫א‬
 Wcombustion ‫א‬‫א‬ -١
–‫א‬‫א‬‫א‬
 K‫א‬K‫א‬‫א‬‫א‬
- ١٨ -
 ‫א‬‫א‬  ١٤٠  ‫א‬
‫א‬‫א‬  ‫א‬‫א‬ ‫א‬
CH4 + 2O2 CO2 (g) + 2H2O + ‫ﻃﺎﻗﺔ‬

 (g)
 WHalogenation‫א‬ -٢
،‫א‬Br2‫א‬Cl2‫א‬E‫א‬‫א‬F‫א‬
‫א‬‫א‬‫א‬ ‫א‬،‫א‬
 ‫א‬
 W‫א‬‫א‬،
 WE١F
Br
+ Br2 + HBr
 Bromocyclopentane

 WE٢F
H
hν
H C H + Cl2 H3C _ Cl + HCl
H Chloromethane
hν 
CH3 Cl + Cl2 CH2Cl2 + HCl
Dicarbomethane

hν
hv
CH 2Cl2 + Cl2 CHCl 3 + HCl
Chloroform

hν
- ١٩ -
 ‫א‬‫א‬  ١٤٠  ‫א‬
‫א‬‫א‬  ‫א‬‫א‬ ‫א‬
hv
C H Cl 3 + Cl2 C C 14 + HCl
Carbontetrachloride'
،‫א‬‫א‬‫א‬
‫א‬‫א‬‫א‬
 W
 K‫א‬EF‫א‬‫א‬ K 
‫א‬‫א‬
 ‫א‬‫א‬‫א‬‫א‬‫א‬
 K‫א‬‫א‬

H 2 /Pt ,Pd ‫ أو‬Ni _ _ _

C C C C
‫ﺿﻐﻂ‬
H H
 Alkene Alkane

H2 , Pt
CH3CH2CH2CH2CH = CH 2 CH3CH2CH2CH2CH2CH2
‫ﺿﻐﻂ‬
1- Hexene n- Hexane
 W K
،‫א‬‫א‬،‫א‬
 ‫א‬ ‫א‬
‫א‬‫א‬‫א‬KGrignard reagents ‫א‬
 K‫א‬‫א‬

‫اﻳ ﺜﺮ ﺟ ﺎف‬
R-X + Mg RMgX
 Alkyl halide Alkyl magnesium halide 

- ٢٠ -
 ‫א‬‫א‬  ١٤٠  ‫א‬
‫א‬‫א‬  ‫א‬‫א‬ ‫א‬

‫א‬‫א‬‫א‬‫א‬
 K‫א‬‫א‬
R-MgX + H 2O RH + Mg(OH)X
 Alkane
RMgX+CH 3OH RH + Mg(OCH 3)X
 Alkane
Br Mg Br
‫اﻳ ﺜﺮ ﺟ ﺎف‬
CH3CH2CHCH 3+Mg CH3CH2CHCH 3
Mg(OH)Br + CH 3CH2CH2CH3 H2O


 W K
 K‫א‬‫א‬‫א‬

2R - X + 2 Na R - R + 2 NaX
 Alkane
 2 CH 3 CH2 Cl + 2 Na CH3 CH2 CH2 CH3
 W‫א‬‫א‬‫א‬‫ א‬K
‫א‬‫א‬‫א‬‫א‬
 ‫א‬‫א‬
،‫א‬‫א‬‫א‬
 W‫א‬‫א‬Lithium dialkyl copper ( R2CuLi)

(CH 3 CH2)2 CuLi + CH 3 CH2 CH2 Br
 CH3 CH2 CH2 CH2 CH3 + CH3 CH2 Cu + LiBr
- ٢١ -
 ‫א‬‫א‬  ١٤٠  ‫א‬
‫א‬‫א‬  ‫א‬‫א‬ ‫א‬

 W‫א‬‫א‬‫א‬‫א‬
 CH 3 CH2 Cl + Li CH 3 CH2 Li

 2 CH 3 CH2 Li + Cul (CH 3 CH2)2 CuLi + Lil
 W‫א‬٢J ٢J ٤
K‫א‬،‫א‬‫א‬‫א‬‫א‬‫א‬
K‫א‬‫א‬‫א‬
  ‫א‬‫א‬،‫א‬‫א‬٪٨٠ ‫א‬
 K‫א‬،‫א‬‫א‬
‫א‬‫א‬ KRefining‫א‬‫א‬
 K












- ٢٢ -
 ‫א‬‫א‬  ١٤٠  ‫א‬
‫א‬‫א‬  ‫א‬‫א‬ ‫א‬
 Walkenes‫א‬٢J ٣
،EC=CF–‫א‬ ‫א‬
،CnH2n‫א‬‫א‬‫א‬،olefins
 KC2H4‫א‬‫א‬CnH2n-2‫א‬

H 120 H
C = C
 H H


 W‫א‬٢J ٣J ١
W‫א‬‫ א‬K
‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬
،‫א‬‫א‬–ylenealkane‫א‬‫א‬‫א‬ ‫א‬–ane
 W‫א‬‫א‬
 K‫א‬‫א‬E1-3-2F
Alkene‫א‬  Alkane‫א‬
 Ethylene CH 2=CH 2  Ethane CH3CH3
 Propylene CH3-CH =CH2 


 Propane CH 3CH 2CH 3
Butylene CH3CH2CH=CH2 

 B-Butylene CH3CH=CHCH3
  n-Butane CH 3CH 2CH 2CH 3
Isobutylene CH3 CH = CH2 Isobutane CH3 CH CH3
 CH3  CH3
- ٢٣ -
 ‫א‬‫א‬  ١٤٠  ‫א‬
‫א‬‫א‬  ‫א‬‫א‬ ‫א‬
– CH2=CH2‫א‬‫א‬‫א‬‫א‬
 W( Vinyl group )‫א‬CH=CH2

CH2 = CH CH 2 = CH CH2 = CH
Cl Br
 Vinyl Chloride  Vinyl bromide 
 Vinyl Cyclohexane

 W( allyl group)‫א‬CH3CH=CH2‫א‬‫א‬‫א‬
CH2CH = CH2
Cl
 Allyl Choride
WIUPAC‫א‬‫ א‬K
‫א‬‫א‬‫א‬،‫א‬‫א‬‫א‬
  ‫א‬E  ‫א‬‫א‬FIUPAC‫א‬
 W‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬
 KE‫א‬F‫א‬‫א‬‫א‬‫א‬‫א‬ E١
–‫א‬‫א‬‫א‬ ‫א‬–ane‫א‬‫א‬‫א‬‫א‬ E٢
Kene
‫א‬‫א‬‫א‬‫א‬،‫א‬‫א‬‫א‬‫א‬‫א‬ E٣
K‫א‬
‫א‬‫א‬‫א‬،‫א‬‫א‬‫א‬
W‫א‬‫א‬،‫א‬‫א‬‫א‬

- ٢٤ -
 ‫א‬‫א‬  ١٤٠  ‫א‬
‫א‬‫א‬  ‫א‬‫א‬ ‫א‬
5 4 3 2 1
CH3CH-CH = CH-CH 3
CH3
 4- Methyl - 2- Pentene

 W‫א‬‫א‬‫א‬
  CH3CH2CH = CH2
CH2 = CH2 CH 3 -CH = CH 2  1-Butene
Ethene Propene 
 

 CH2-CH = CH2
Cl
 3-Chloro -l- Propene
 2-Ethyl-1-Butene 

‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬
‫א‬K‫א‬ ‫א‬‫א‬،‫א‬‫א‬‫א‬
K‫א‬‫א‬‫א‬‫א‬‫א‬
6
3
5 1 4 2
4 2
3 5 1
6
Cyclohexene 3-Methylcyclohexene
 (1-Cyclohexene‫)وﻟﻴﺲ‬  (6-Methylcyclohexene ‫)وﻟﻴﺲ‬
–ene‫א‬‫א‬‫א‬‫א‬KKKKKKtetra،tri ،di ‫א‬

‫א‬‫א‬‫א‬‫א‬
K‫א‬‫א‬‫א‬‫א‬

- ٢٥ -
 ‫א‬‫א‬  ١٤٠  ‫א‬
‫א‬‫א‬  ‫א‬‫א‬ ‫א‬

4 3 2
5
5
CH2 = CH-CH 2-C-CH 2CH3 1 4
1 CH 2
2 3
 2-Ethyl,1,4-Pentadiene  1,3-Cyclopentadiene
 

2 4 6
1 3 5 7
 1,3,6-Heptatriene 

‫א‬F‫א‬‫א‬‫א‬‫א‬ 
‫א‬E2-butane 1-butene‫א‬‫א‬‫א‬
K‫א‬‫א‬‫א‬‫א‬،‫א‬‫א‬
W2-butene
 
H CH3 CH3 CH3
C C C C
H H
CH3 H
 Cis-2-butene 
 trans-2-butene  

E‫א‬‫א‬‫א‬‫א‬F‫א‬‫א‬
 –cisF‫א‬،‫א‬
F‫א‬‫א‬،E
،‫א‬‫א‬Ktrans‫א‬E‫א‬
trans-2- ٣٧،‫א‬،cis-2-butene ،‫א‬‫א‬‫א‬
 K ٠{٩butene
- ٢٦ -
 ‫א‬‫א‬  ١٤٠  ‫א‬
‫א‬‫א‬  ‫א‬‫א‬ ‫א‬
 W‫א‬‫א‬‫א‬٢J ٣J ٢
‫א‬‫א‬ ‫א‬‫א‬‫א‬ ‫א‬‫א‬
،‫א‬،‫א‬،‫א‬‫א‬
‫א‬‫א‬،‫א‬‫א‬‫א‬‫א‬ ‫א‬
‫א‬‫א‬
 ‫א‬‫א‬‫א‬ ،‫א‬
 K‫א‬
 W‫א‬٢J ٣J ٣
 W‫א‬‫א‬
W‫א‬‫א‬‫א‬‫א‬ E٤
‫א‬‫א‬‫א‬‫א‬،H+،‫א‬
KH3PO4‫א‬H2SO4‫א‬‫א‬

H H H H
+
H ,
H C C H C C + H2O
OH H H H
(‫آﺤﻮل )اﻳﺜﺎﻧﻮل‬ (‫اﻟﻜﻴﻦ )اﺛﻴﻠﻴﻦ‬



 ‫א‬F‫א‬‫א‬‫א‬‫א‬ ،‫א‬‫א‬‫א‬
،‫א‬‫א‬E‫א‬ ‫א‬‫א‬‫א‬‫א‬‫א‬
 W‫א‬‫א‬
+
H ,
CH2 CH CH CH3 CH3-CH = CHCH3
H 2-Butene
OH H
2-Butanol + + H2O
CH3=CHCH2CH3
1-Butene
- ٢٧ -
 ‫א‬‫א‬  ١٤٠  ‫א‬
‫א‬‫א‬  ‫א‬‫א‬ ‫א‬
W‫א‬‫א‬‫א‬‫א‬ E٥
 KKOH‫א‬‫א‬( I , Br, Cl =X ) HX 
KOH / ‫آﺤﻮل‬ + -
CH2 CH2 CH2 = CH2 +K +CI +H2O
H Cl ‫اﺛﻴﻠﻴﻦ‬
 ‫آﻠﻮرو اﻳﺜﺎن‬ 
،‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬،‫א‬‫א‬‫א‬‫א‬
 W‫א‬‫א‬،‫א‬


KOH / ‫آﺤﻮل‬
CH2 CH CH CH3 CH3 CH = CH CH3 + K+
H Br H
 
 J ٢EFJ ٢

 H+Br-+H2o
 
 CH2 = CHCH2CH3
 EFJ ١
 W‫א‬ H2SO4‫א‬‫א‬ K١
‫א‬‫א‬،‫א‬‫א‬‫א‬
‫א‬K‫א‬‫א‬
  ‫א‬‫א‬‫א‬،‫א‬
 K

- ٢٨ -
 ‫א‬‫א‬  ١٤٠  ‫א‬
‫א‬‫א‬  ‫א‬‫א‬ ‫א‬
CH2 = CH2 + H2SO4 ‫ﻣﺮآﺰ‬ CH2 CH2
H OSO3H
 ‫آﺒﺮﻳﺘﺎت اﻻﻳﺜﻴﻞ اﻟﻬﻴﺪروﺟﻴﻨﻴﺔ‬ 
 
 WPolymerization‫ א‬K٢
‫א‬––‫א‬
 
،‫א‬‫א‬‫א‬‫א‬ Kpolymers‫א‬
K‫א‬‫א‬‫א‬‫א‬
W‫א‬‫א‬W
 ‫א‬Naphtha fraction‫א‬‫א‬‫א‬‫א‬ 
١٠J ٤‫א‬‫א‬‫א‬‫א‬،‫א‬
،٩٠٠J ٧٠٠‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬
 K‫א‬‫א‬‫א‬‫א‬‫א‬
‫א‬‫א‬‫א‬‫א‬‫א‬  ‫א‬‫א‬‫א‬‫א‬
K‫א‬‫א‬
،ECr2O3+Al2O3) ‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬
K‫א‬‫א‬
Cr2O3 +Al2O3
CH3CH2CH3 CH2 = CHCH3
700cْ 


 W( X = Cl ,Br, I ) HX‫א‬
 
- ٢٩ -
 ‫א‬‫א‬  ١٤٠  ‫א‬
‫א‬‫א‬  ‫א‬‫א‬ ‫א‬
C C + HX C C
H X
  ‫هﺎﻟﻴﺪ اﻟﻜﻴﻞ‬ 

CH2=CH2 + HCI CH 3 CH2 CI
 (‫آﻠﻮرو اﻳﺜﺎن )آﻠﻮرﻳﺪ اﺛﻴﻞ‬ 

‫א‬،‫א‬‫א‬‫א‬
،‫א‬‫א‬‫א‬‫א‬،‫א‬‫א‬‫א‬
 K‫א‬‫א‬Markovnikov's Rule 
CH2 = CHCH3 + HCl CH2 CH CH3
 H Cl

 J ٢

 WHydration ‫א‬
‫א‬K‫א‬H+‫א‬‫א‬
 ‫א‬
 K
+
H
CH2 = CHCH3 + H2O CH2 CH CH3
  H OH 

 J ٢

- ٣٠ -
 ‫א‬‫א‬  ١٤٠  ‫א‬
‫א‬‫א‬  ‫א‬‫א‬ ‫א‬
 W‫א‬٢J ٣J ٤
‫א‬K،‫א‬‫א‬‫א‬
 W‫א‬K‫א‬‫א‬
 WHydrogenation‫ א‬.١
 K‫א‬CatalystsE‫א‬FPdNi Pt ‫א‬‫א‬
Pt or Ni
CH2 = CH2 + H2 CH3 CH3
 ‫اﺛﻴﻠﻴﻦ‬ ‫إﻳﺜﺎن‬

،‫א‬‫א‬‫א‬،‫א‬‫א‬
 ‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬
 WHalogenations‫ א‬.٢
‫א‬
 ‫א‬‫א‬‫א‬‫א‬
 K‫א‬
 
C C + X2 / CCI4 C C
 (X = CI , Br) X X 

 
CH2 = CH2 + Br2 / CCI4 CH2 CH2
 Br Br 
 
،E–‫א‬‫א‬‫א‬F‫א‬‫א‬‫א‬‫א‬ ‫א‬
 K‫א‬‫א‬‫א‬

- ٣١ -
 ‫א‬‫א‬  ١٤٠  ‫א‬
‫א‬‫א‬  ‫א‬‫א‬ ‫א‬
 WAlkynes‫א‬٢J ٤
J F–‫א‬ ‫א‬ 
‫א‬‫א‬،CnH2n-2‫א‬‫א‬KEJ C C
،‫א‬sp‫א‬‫א‬،‫א‬‫א‬،C2H2‫א‬
‫א‬K‫א‬‫א‬
‫א‬‫א‬‫א‬، ٣٠٠٠‫א‬‫א‬‫א‬
 K‫א‬
CaO‫א‬‫א‬‫א‬
 K‫א‬CaS2‫א‬،
2500 oC
3C + CaO CaC2 + CO
CaC2 + 2H2O C2H2 + Ca(OH) 2
 W‫א‬٢J ٤J ١
EIUPAC‫א‬F ‫א‬‫א‬‫א‬ ‫א‬
‫א‬‫א‬،‫א‬‫א‬،‫א‬‫א‬‫א‬
‫א‬‫א‬‫א‬‫א‬،
 W‫א‬‫א‬–ene ‫א‬–yne‫א‬
HC CH CH3C CH CH3CH2C CH
Acetylene Methyl acetylene Ethyl acetylene 
Ethyne 1- Butyne 

 Propyne
- ٣٢ -
 ‫א‬‫א‬  ١٤٠  ‫א‬
‫א‬‫א‬  ‫א‬‫א‬ ‫א‬
 WIUPAC‫א‬‫א‬
CH3 CH3
CH3C CCH3
CH3CH CH C C CH2CH CH3
2-Butyne
Cl
3-Chloro-2,7-dimethyl-4-octyne
CH C C CH
1,3-Butadiyne

‫א‬‫א‬ ‫א‬‫א‬
‫א‬‫א‬–yne‫א‬‫א‬‫א‬‫א‬‫א‬‫ א‬،‫א‬
 Kalkene‫א‬‫א‬‫א‬،‫א‬‫א‬‫א‬
HC CH CH2 CH CH2
1-Penten-4-yne
‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬
 K‫א‬–yne ‫א‬
 W‫א‬‫א‬‫א‬٢J ٤J ٢
‫א‬‫א‬‫א‬‫א‬  ‫א‬
‫א‬،‫א‬K‫א‬‫א‬
C17‫א‬C16C4 ‫א‬،‫א‬C4C2
 K‫א‬
- ٣٣ -
 ‫א‬‫א‬  ١٤٠  ‫א‬
‫א‬‫א‬  ‫א‬‫א‬ ‫א‬
 W‫א‬٣J ٣J ٤
‫א‬‫א‬
 ‫א‬‫א‬
 W‫א‬‫א‬‫א‬
Dehydrohalgenation W‫א‬‫א‬‫א‬‫א‬ .١
 W

KOH
CH3CH CH H [ CH3CH = C H]
EtOH
Br Br Br
1,2-Dibromopropane Allylbromide
NaNH2 /
CH3 C C H
Propyne

 W‫א‬‫א‬ .٢
 W‫א‬‫א‬‫א‬‫א‬
- liq NH 3
HC C Na+ + CH3Br HC C CH3 + NaBr
- liq NH3
HC C Na+ + CH3CH2I HC C CH2CH3 + NaI
- liq NH3
CH3 C C Na+ + CH3CH2Br CH3 C C CH2CH3 + NaBr
Sodium propynide
- ٣٤ -
 ‫א‬‫א‬  ١٤٠  ‫א‬
‫א‬‫א‬  ‫א‬‫א‬ ‫א‬
‫א‬ ‫א‬‫א‬‫א‬‫א‬
 ‫א‬‫א‬
 K‫א‬‫א‬‫א‬‫א‬
 W‫א‬‫א‬‫א‬‫א‬
‫א‬‫א‬‫א‬‫א‬ ‫א‬
 W‫א‬‫א‬‫א‬‫א‬،‫א‬‫א‬
‫א‬‫א‬‫א‬‫א‬W‫א‬‫א‬‫א‬ J ١
W‫א‬‫א‬‫א‬‫א‬
CH4 + O2 2HC CH + 2CO + 10H2
‫א‬‫א‬‫א‬‫א‬W‫א‬ J ٢
،‫א‬‫א‬‫א‬‫א‬،‫א‬
E‫א‬F‫א‬‫א‬‫א‬‫א‬
‫א‬‫א‬‫א‬‫א‬
W‫א‬
CaCO3 CaO + CO2
 Calcium carbonate
2500
CaO + 3C CaC2 + CO
Coke Calcium carbide
ْ C
25
CaC2 + 2H2O HC CH + Ca(OH)2
Acetylene
- ٣٥ -
 ‫א‬‫א‬  ١٤٠  ‫א‬
‫א‬‫א‬  ‫א‬‫א‬ ‫א‬
 W‫א‬٢J ٤J ٣
 W‫א‬‫א‬‫א‬‫א‬
‫א‬‫א‬‫א‬،‫א‬‫א‬‫א‬
 W‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬K
 W‫א‬ .١
‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬
 K‫א‬‫א‬،‫א‬
R R
Pd or Ni H2\Ni
R C C R + H2 C=C RCH2CH2R
H H

Ni-
 ‫א‬‫א‬ ‫א‬‫א‬
 
Linders catalyst Pd + Pb(OAc)4‫א‬‫א‬‫א‬B2
 KPd/CaCO3)
 W‫א‬‫ א‬.٢
 ‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬
 W‫א‬‫א‬
Cl Cl Cl
CH3 C C CH3 + Cl2 CH3 C = C CH3 CH3 C C CH3

Cl Cl Cl
1,1,2,2-Tetrachlorobutane
- ٣٦ -
 ‫א‬‫א‬  ١٤٠  ‫א‬
‫א‬‫א‬  ‫א‬‫א‬ ‫א‬
 W‫א‬‫א‬ .٣
‫א‬‫א‬‫א‬‫א‬‫א‬
‫א‬‫א‬‫א‬‫א‬‫א‬،
 K‫א‬‫א‬‫א‬‫א‬‫א‬
Cl
HCl HCl
CH3 C CH CH3C = CH 2 CH3 C CH3
Cl Cl
2,2-Dichloropropane
 W‫א‬ .٤
‫א‬‫א‬‫א‬‫א‬
‫א‬،mercuric sulfate ‫א‬
 K‫א‬‫א‬
O
H H
HgSO4
CH CH + H2O C=C CH3 C H
H2SO4
H OH
Enol Acetaldehyde
OH O
HgSO4
CH3 C CH + H2O CH3 C = CH2 CH3 C CH3
H2SO4
 Acetone
- ٣٧ -
 ‫א‬‫א‬  ١٤٠  ‫א‬
‫א‬‫א‬  ‫א‬‫א‬ ‫א‬
 W‫א‬ .٥
‫א‬‫א‬‫א‬ ‫א‬‫א‬‫א‬ ‫א‬
 W‫א‬‫א‬
O O
-
1)KMnO4 /OH
- R C C Rَ
2)H2O / OH
O O
-
1)KMnO4 /OH
R C C Rَ R C OH + Rَ C OH
ْ C/H +
2) 100
1)O3
RCOOH + RَCOOH
2)H2O /Zn Or H2O2
 ‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬٢J ٤J ٤
‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬
‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬K‫א‬
‫א‬‫א‬(PVC)  ‫א‬‫א‬
‫א‬‫א‬A‫א‬‫א‬‫א‬‫א‬
 K‫א‬‫א‬
‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬
 KPayragyline ‫א‬‫א‬







- ٣٨ -
 ‫א‬‫א‬  ١٤٠  ‫א‬
‫א‬‫א‬  ‫א‬‫א‬ ‫א‬
 2-5

 WIUPAC‫א‬‫א‬‫א‬‫א‬J ١

CH3CHCHCHCH 3
-‫ب‬  CH3-C(CH3)2CH3 J 
 Br Cl CH3
CH3
CH3CH2CH2 C = CH2
J  J 
C2H5
CH3
J  CH C CH J 
CH3
CH3 C = C CH3
J 
CH3 Br


 W‫א‬‫א‬‫א‬‫א‬‫א‬–٢


2-bromo-2-methyloctane 2,3-dimethylbutane J 
J
2-chloro-3-methyl-2-pentene J  1,1-dimethylcyclohexane J 
2,2-Dibromo-3-hexyne J  2,3Dimethyl-1,4-cyclohexadiene J 
 ‫؟‬‫א‬C6H14‫א‬‫א‬‫א‬‫א‬‫א‬–٣

 ‫؟‬‫א‬‫א‬‫א‬‫א‬‫א‬–٤
- ٣٩ -
 ‫א‬‫א‬  ١٤٠  ‫א‬
‫א‬‫א‬  ‫א‬‫א‬ ‫א‬
 W‫א‬‫א‬–٥
CH3CH3 + Cl2 hυ
J 
CH4 + 2O2 J 
CH3CH2Cl + Na J 
CH3CH2OH H+,∆
J 
CH3CH=CH2 Pt or Ni
J 
CCl
CH3CH=CHCH3 + Br2 4 J 
CCl4
+ Cl2 J 
KOH NaNH2 /
CH3CH CH CH3 J 
EtOH
Br Br
CH3 C C CH3 + 2Cl2 J 
HgSO4
CH3 C CH J 
H2SO4
 W،–٦

i) CH3CH3 ii) CH3CH2Cl iii) CH2 = CH2
 W‫א‬‫א‬‫א‬–٧
3-Bromo-1-pentyne , 4-Methyl-2-hexene
 W‫א‬‫א‬‫א‬
H2 , Br2/H2O , H2O/H+ , HCl
- ٤٠ -
 ‫א‬‫א‬  ١٤٠  ‫א‬
‫א‬‫א‬  ‫א‬‫א‬ ‫א‬
 ٢J ٥‫א‬
 W١
2,2- Dimethyl Propane -‫ا‬ .١
3-Ethyl-1-Methyl cyclohexane -‫ﺟـ‬ .٢
3-Methyl -1- butyne -‫هـ‬ .٣
 2- Bromo -3-Methyl -2- buteneJ 

 W٢
.٤
CH3 - CH -CH -CH3
CH3 CH3 .٥
CH 3 C C CH 2CH 3
Cl CH 3 .٦
Br
CH 3 C C CH 2CH 3
Br .٧
 K‫א‬‫א‬‫א‬‫א‬W٤
 W٥
CH4 +2O 2 CO2 + 2H2O + ‫ﻃﺎﻗﺔ‬ .٢ J  K١
+
CH3 CH2 OH
H ,
CH2 = CH2 + H2O .٤ J  K٣
CCI4
CH3 - CH = CH - CH 3 + Br2 CH2CH - CH CH 3
J  K٥
Br Br .٦
- ٤١ -
 ‫א‬‫א‬‫א‬
‫א‬‫א‬‫א‬‫א‬
‫א‬‫א‬
‫א‬‫א‬
 ‫א‬‫א‬
٣
 ‫א‬‫א‬  ١٤٠  ‫א‬
 ‫א‬‫א‬  ‫א‬‫א‬ ‫א‬
 W‫א‬‫א‬
،‫א‬‫א‬‫א‬،‫א‬‫א‬ ‫א‬‫א‬‫א‬‫א‬
 K‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬
 W‫א‬‫א‬
 W‫א‬‫א‬‫א‬
 K‫א‬‫א‬ .١
K‫א‬‫א‬ .٢
K‫א‬‫א‬‫א‬‫ א‬.٣
K‫א‬‫א‬ .٤
 W‫א‬‫א‬‫א‬
 K٪٩٠‫א‬‫א‬‫א‬
 W‫א‬‫א‬
 K٤
 W‫א‬‫א‬
K‫א‬‫א‬‫א‬‫א‬‫א‬ .٢
K .٣
 W‫א‬‫א‬
 K‫א‬‫א‬‫א‬‫א‬
- ٤٢ -
 ‫א‬‫א‬  ١٤٠  ‫א‬
 ‫א‬‫א‬  ‫א‬‫א‬ ‫א‬
 W1J 3
‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬
‫א‬‫א‬‫א‬K‫א‬‫א‬‫א‬
 ‫א‬
 K‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬
E‫א‬‫א‬‫א‬‫א‬F‫א‬EAromatic) ‫א‬‫א‬
،J OCH3  ‫א‬‫א‬‫א‬
J C6H5‫א‬‫א‬J J J J J COOCH3،J COOH
،J C6H5‫א‬‫א‬‫א‬
EF‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬ ،‫א‬‫א‬‫א‬‫א‬
 K‫א‬‫א‬
 W‫א‬2J 3
‫א‬‫א‬‫א‬‫א‬‫א‬C6H6‫א‬
‫א‬،‫א‬K‫א‬‫א‬‫א‬‫א‬ ‫א‬
‫א‬K‫א‬sp2‫א‬‫א‬،‫א‬‫א‬‫א‬
‫א‬‫א‬‫א‬، (A˚١٣٩F‫א‬‫א‬–
‫א‬‫א‬KE١٥٤A˚)C-C‫א‬‫א‬‫א‬،E١٣٢A˚)C=C
 WKekule ‫א‬‫א‬

 I II
 ‫א‬Hybrid‫א‬‫א‬KII،I‫א‬
‫א‬‫א‬‫א‬‫א‬KII،I
 Delocaized
- ٤٣ -
 ‫א‬‫א‬  ١٤٠  ‫א‬
 ‫א‬‫א‬  ‫א‬‫א‬ ‫א‬
 W‫א‬‫א‬3J 3
 W‫א‬‫א‬‫א‬‫א‬‫א‬
‫א‬‫א‬‫א‬‫א‬‫א‬ K١
FP‫א‬‫א‬‫א‬EF
KE‫א‬
K‫א‬ K٢
K‫א‬‫א‬‫א‬ K٣
‫א‬‫א‬‫א‬EHuckels ruleF K٤
En = 0,1,2,3KKKKKKKFE4n+2)‫א‬‫א‬π‫א‬‫א‬
‫א‬Eπ‫א‬F‫א‬‫א‬
WE٦F‫א‬‫א‬E١Fn‫א‬

 (4x1+2) = 6
E‫א‬‫א‬F‫א‬‫א‬‫א‬‫א‬‫א‬
 W‫א‬

 
 Benzen Naphthalene Anthracene
 n =1  n =2 n =3
- ٤٤ -
 ‫א‬‫א‬  ١٤٠  ‫א‬
 ‫א‬‫א‬  ‫א‬‫א‬ ‫א‬
..
N N
 .. 
Pyridine Pyrole
 Phenanthrene  n =1
 n =1
4(1)+2=6 πes
n=3 4(1)+2=6 πes
 4(3)+2=14 πes
+
+ -
 
 n=0  n =1 
4(0)+2=2 πes n =1
4(1)+2=6 πes
 4(1)+2=6 πes
 W‫א‬‫א‬‫א‬

- +
 W‫א‬‫א‬‫א‬4J 3
‫א‬‫א‬º٨٠K  ‫א‬،‫א‬‫א‬
‫א‬‫א‬ ‫א‬‫א‬º٤{٥

 Kπ‫א‬‫א‬‫א‬
- ٤٥ -
 ‫א‬‫א‬  ١٤٠  ‫א‬
 ‫א‬‫א‬  ‫א‬‫א‬ ‫א‬
 W‫א‬4J 3
 ‫א‬‫א‬‫א‬‫א‬
 W‫א‬
W‫א‬‫א‬‫א‬‫א‬‫א‬ K١
 W‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬

Br I CH2CH3
  
Bromobenzene Iodobenzene Ethylbenzene
NO2

Nitrobenzene
 W‫א‬
CH3 CH=CH2 CH _ CH _ CH CHO

3 3
 
Toluene Styrene  Cumene Benzaldehyde
O
OH COOH NH2
C _ CH3
 
Phenol Benzoic acid  Aniline
Acetopnenone
- ٤٦ -
 ‫א‬‫א‬  ١٤٠  ‫א‬
 ‫א‬‫א‬  ‫א‬‫א‬ ‫א‬
SO3H OCH3
 
Anisole
Benzenesulfonic acid
‫א‬ ،‫א‬‫א‬‫א‬‫א‬
 K‫א‬‫א‬‫א‬‫א‬‫א‬phenyl

CH3CHCH2CH3 CH2CH2OH
 
 2-Phenylbutane 2-Phenylethanol

Benzyl‫א‬‫א‬‫א‬
‫א‬‫א‬‫א‬، Benzal‫א‬‫א‬
 KBenzo
 
CH2Cl CHCl2 CCl3
  
Benzylchloride  Benzalchloride  Benzotrichloride

 ‫א‬ K٢
ortho EOF‫א‬‫א‬‫א‬K‫א‬‫א‬
‫א‬  meta EmF ‫א‬ ‫א‬    ‫א‬ ‫א‬ 
- ٤٧ -
 ‫א‬‫א‬  ١٤٠  ‫א‬
 ‫א‬‫א‬  ‫א‬‫א‬ ‫א‬
 ‫א‬   K  para Ep F ‫א‬ ‫א‬   ‫א‬
K Benzene ‫א‬ K‫א‬‫א‬
W‫א‬‫א‬،‫א‬‫א‬،‫א‬
F
CI CH2CH3
CI
 CI
 I
 O-dichlorobenzene m-chloroethylbenzene p-fluoroiodobenzene
CH 3 COOH OH
CI
 NO 2 
 Br
m-nitrotoluene m-bromobenzoic acid o-chlorophenol
 W‫א‬‫א‬CH3-
CH3 CH3 CH 3
CH3
  CH3  CH 3
 o-xylene  m-xylene  p-xylene
 ‫א‬‫א‬
CI NO2
2
1
CI 1 CI 6 2
3
5 3
6 4 CI
F
 5  4
 
 1,2,3-trichlorobenzene  3-chloro-5-fluronitrobenzene
  ‫א‬F
 (1,2,6-trichlorobenzene)  E١‫א‬
 
- ٤٨ -
 ‫א‬‫א‬  ١٤٠  ‫א‬
 ‫א‬‫א‬  ‫א‬‫א‬ ‫א‬
OH CH3
1
Br Br NO2 NO2
6 2
5 3
4
 Br  NO2
 
2,4,6-tribromophenol 2,4,6-trinitrotoluene (TNT)
‫א‬) ‫א‬F
E١‫א‬  E١‫א‬

 W‫א‬‫א‬٣J ٦
،‫א‬‫א‬‫א‬‫א‬‫א‬،‫א‬
‫א‬‫א‬‫א‬K‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬
‫א‬‫א‬‫א‬‫א‬‫א‬
‫א‬‫א‬‫א‬‫א‬‫א‬
‫א‬،
 K‫א‬
_
Al2O3 CrO3 / 500ْ C
CH3
CH3(CH2)5CH3 + 3H2
Pt / 400ْ C
Toluene K
CH3 Al2O3 _ Pt
+ 3H2
ْ
550 C
Benzene
- ٤٩ -
 ‫א‬‫א‬  ١٤٠  ‫א‬
 ‫א‬‫א‬  ‫א‬‫א‬ ‫א‬
 W‫א‬‫א‬٣J ٧
‫א‬‫א‬‫א‬،‫א‬‫א‬ 
 K‫א‬‫א‬‫א‬‫א‬،‫א‬‫א‬‫א‬
 W‫א‬‫א‬‫א‬ .١
‫א‬‫א‬‫א‬ ‫א‬‫א‬
 W‫א‬
 WHalogenation‫א‬ K
 ‫א‬،‫א‬
‫א‬‫א‬،‫א‬‫א‬E‫א‬‫א‬‫א‬F‫א‬
،E‫א‬‫א‬F‫א‬‫א‬‫א‬‫א‬‫א‬،
‫א‬،‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬
‫א‬‫א‬K‫א‬
‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬،‫א‬‫א‬
‫א‬‫א‬‫א‬‫א‬‫א‬
 K‫א‬
CH2Cl CHCl2 CCl3
CI2 Cl2 Cl2
/ً‫ﺿﻮ‬ / ً ‫ﺿﻮ‬ / ً ‫ﺿﻮ‬
CH3
Benzoyl Benzoal Benzotrichoride
choride choride
CH3 CH3
Cl2/FeCl3
CI
Toluene
+
Cl
 o-chlorotoluene p-chlorotoluene
- ٥٠ -
 ‫א‬‫א‬  ١٤٠  ‫א‬
 ‫א‬‫א‬  ‫א‬‫א‬ ‫א‬
 W‫א‬‫א‬ K
‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬
‫א‬‫א‬‫א‬‫א‬‫א‬
‫א‬‫א‬‫א‬ ‫א‬‫א‬‫א‬K
  ‫א‬‫א‬‫א‬
 ‫א‬
 K

CH3 COOH
KMnO4 or
K2Cr2O7
 Benzoic acid
CH2CH2CH3 COOH
CH3 COOH
KMnO4 or
+ (CO2 + H2O)
K2Cr2O7
Phthalic acid
 ( 1,2- benzenedicarboxylic acid)
W‫א‬ .١
W‫א‬ -‫أ‬
،‫א‬‫א‬‫א‬
EthylbenzeneK‫א‬،‫א‬‫א‬‫א‬
 KCyclohexane 
CH 2CH 3 CH 2CH 3
Ni,Pt or Pd
+ 3H 2
Ethylcyclohexane
 Ethylbenzene
- ٥١ -
 ‫א‬‫א‬  ١٤٠  ‫א‬
 ‫א‬‫א‬  ‫א‬‫א‬ ‫א‬
 W‫א‬‫א‬‫א‬‫א‬
‫א‬E‫א‬‫א‬‫א‬‫א‬F‫א‬
،‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬
‫א‬،‫א‬‫א‬‫א‬
‫א‬‫א‬‫א‬‫א‬، 
،‫א‬‫א‬‫א‬‫א‬K‫א‬
،‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬
‫א‬‫א‬‫א‬‫א‬‫א‬
 W‫א‬‫א‬‫א‬‫א‬‫א‬ ،‫א‬‫א‬‫א‬
Alkylation E‫א‬–F J ١
CH3
AlCl3
+ CH3Cl + HCl


AcylationE‫א‬–F J ٢
O
O C _ CH 3
AlCl 3
_ _
+ CH3 C Cl


Halogenation‫א‬ J ٣

Br
FeBr3
+ Br2

- ٥٢ -
 ‫א‬‫א‬  ١٤٠  ‫א‬
 ‫א‬‫א‬  ‫א‬‫א‬ ‫א‬
Nitroation‫א‬ J ٤
NO2
H2SO4(conc.)
+ HNO3

‫א‬ J ٥
SO3H Sulfonation
SO3
+ H2SO4 
 W‫א‬‫א‬‫א‬٣J ٨
،‫א‬‫א‬
 ‫א‬‫א‬‫א‬
‫א‬
 ‫א‬‫א‬‫א‬‫א‬K‫א‬‫א‬‫א‬
AnisoleK‫א‬‫א‬،
K nitroanizole ‫א‬‫א‬‫א‬‫א‬
 K‫א‬‫א‬‫א‬
OCH3 OCH3 OCH3
HNO3 NO2
H2SO4 +
 NO2
‫א‬‫א‬
‫א‬‫א‬–‫א‬
 K‫א‬
NO2 NO2
HNO 3
H2SO4
 NO2
- ٥٣ -
 ‫א‬‫א‬  ١٤٠  ‫א‬
 ‫א‬‫א‬  ‫א‬‫א‬ ‫א‬
=O،R+F‫א‬‫א‬‫א‬‫א‬‫א‬
‫א‬‫א‬‫א‬‫ א‬ ‫א‬EH+،Br+،NO2+،CH3C+
‫א‬‫א‬‫א‬‫א‬،‫א‬

 ‫א‬‫א‬‫א‬‫א‬‫א‬،‫א‬
 W‫א‬
 ‫א‬–‫א‬ .١
 W‫א‬‫א‬‫א‬‫א‬
 -NH2(-NHR,-NR2) ,-OH >-OR,-NHCOCH3 > -C6H5 ,-R
 K‫א‬ERF
K‫א‬‫א‬–‫א‬ .٢
 E-F,-Cl, - Br )
W‫א‬‫א‬K‫א‬ .٣
 K-NO2, -N+(R)3,-C=N,COOH( -COOR ),-SO3H,-CHO,-COR
 
 W‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬
‫א‬،‫א‬
 K‫א‬‫א‬‫א‬
- ٥٤ -
 ‫א‬‫א‬  ١٤٠  ‫א‬
 ‫א‬‫א‬  ‫א‬‫א‬ ‫א‬
NO2 NO2
HNO3 Br2,Fe
H2SO4
Br
m-bromonitobenzene
Br Br Br
NO2
Br2,Fe HNO3
+
H2SO4
NO2
o-bromonitro p-bromonitro
 benzene (38%) benzene (62%)
 W‫א‬‫א‬‫א‬٣J ٩
‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬
‫א‬
 K‫א‬
‫א‬K‫א‬،‫א‬‫א‬،EF
‫א‬‫א‬KE‫א‬F‫א‬
‫א‬‫א‬‫א‬‫א‬‫א‬K‫א‬،
 K‫א‬‫א‬‫א‬‫א‬،‫א‬‫א‬‫א‬
 







- ٥٥ -
 ‫א‬‫א‬  ١٤٠  ‫א‬
 ‫א‬‫א‬  ‫א‬‫א‬ ‫א‬
 
 W‫א‬‫א‬‫א‬W١

CH = CH 2 COOH CH3
Br NO2
a) b) c)
CH3
CH3 COOH
CI
d) e)
I I NO 2

 W‫א‬‫א‬‫א‬‫א‬‫א‬W٢
a) 1,3,5-trichloro benzen b) m-bromotoluene
c) p-bromoniro benzene d) lsopropyl benzene
e) 4-bromo-2,3-dinitrotoluene f) m-chloro benzoic acid

 W‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬W٣

CH(CH 3)2
-
KMnO 4 / OH
 
CH 3
Br 2 /hv
- ٥٦ -
 ‫א‬‫א‬  ١٤٠  ‫א‬
 ‫א‬‫א‬  ‫א‬‫א‬ ‫א‬
NO 2
Br 2
FeBr 3
OC 2H5
AICI 3
+ CH 3CH 2CI
CI
O
AICI 3
+ CH 3 C - CI
CH 3
H 2O 3
HNO 3
AICI 3
+ CH 3 CHCI CH 3
CN
Br 2
FeBr 3









- ٥٧ -
 ‫א‬‫א‬  ١٤٠  ‫א‬
 ‫א‬‫א‬  ‫א‬‫א‬ ‫א‬
 ٣J ٨
 W١
O-Bromostyrene J ‫א‬
3,5- Diiodo tolueneJ 

 W٢
CH3
 Br2
CH (CH 3)2
 
 W٣
CH(CH 3)2 COOH
-
KMnO 4/OH
NO2 NO 2
Br 2
FeBr 3
Br
CH3 CH3 CH3
NO2
HNO2
+
H2SO4
NO2
CH (CH 3) 2
AICI 3
+ CH 3 CHCI CH 3
 
- ٥٨ -
 ‫א‬‫א‬‫א‬
‫א‬‫א‬‫א‬‫א‬
‫א‬‫א‬
‫א‬‫א‬‫א‬
 ‫א‬‫א‬‫א‬
٤
 ‫א‬‫א‬‫א‬  ١٤٠  ‫א‬
 ‫א‬‫א‬‫א‬  ‫א‬‫א‬ ‫א‬
 W‫א‬‫א‬
‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬
 ‫א‬‫א‬
 K‫א‬‫א‬‫א‬
 W‫א‬‫א‬
 W‫א‬‫א‬‫א‬
 K‫א‬‫א‬‫א‬ .١
K‫א‬‫א‬‫א‬‫א‬‫א‬ .٢
K‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬‫ א‬.٣
 W‫א‬‫א‬‫א‬
 K٪٨٠‫א‬‫א‬‫א‬
 W‫א‬‫א‬
 K
 W‫א‬‫א‬
K‫א‬‫א‬ .٢
K .٣
 W‫א‬‫א‬
 K‫א‬‫א‬‫א‬‫א‬
- ٥٩ -
 ‫א‬‫א‬‫א‬  ١٤٠  ‫א‬
 ‫א‬‫א‬‫א‬  ‫א‬‫א‬ ‫א‬
 1J 4
، ‫א‬‫א‬‫א‬‫א‬
R،R - X‫א‬‫א‬،‫א‬‫א‬‫א‬ 
‫א‬‫א‬‫א‬‫א‬‫א‬،X،
 K‫א‬‫א‬‫א‬‫א‬‫א‬،‫א‬
 ‫א‬‫א‬‫א‬2J 4
،‫א‬‫א‬‫א‬‫א‬‫א‬ ‫א‬
‫א‬K‫א‬‫א‬
 ‫א‬‫א‬‫א‬
 ‫א‬‫א‬‫א‬‫א‬
K‫א‬‫א‬‫א‬‫א‬W‫א‬‫א‬
‫א‬F‫א‬Alkyl‫א‬ ‫א‬
 ‫א‬
‫א‬‫א‬EF‫א‬IUPAC‫א‬‫א‬،E
 W‫א‬‫א‬

CH3Cl CH3CH2CH2Br
1˚ halides
 (Methyl chloride) (n – propyl bromide)
‫א‬
 Chloromethane 1 - Bromopropane

CI
I
CH3 - CH - CH3 2ºhalides
EIsopropyl iodide) ‫א‬
(Cyclopentyl chloride)
2- Iodopropane
Chlorocyclopentane
CH3 CH3
CH3 - CH2 - CH2 - C - CH = CH2 CH3 - C - CH3 3º halides
‫א‬
Br Br
3-Bromo-3-methyl-1-hexene (tert-Butyl bromide)
- ٦٠ -
 ‫א‬‫א‬‫א‬  ١٤٠  ‫א‬
 ‫א‬‫א‬‫א‬  ‫א‬‫א‬ ‫א‬
 W‫א‬‫א‬‫א‬‫א‬
_ CH2 = CH
CH2 = CH CH2
CH2X
X X
Allylhalide Vinylhalide Benzylhalide

 W‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬

CCl4 CHCl3 CH2Cl2
(Carbontetrachloride) (Chloroform) (Methylene chloride)
Tetrachloromethane Trichloromethane Dichloromethane
Br
CHBr3 CHI3
CH3 - C - CH2CH3
(Bromofoem) (Iodoform) Br
2,2-Dibromobutane
 ‫א‬‫א‬‫א‬3J 4
‫א‬،‫א‬
 ‫א‬ ‫א‬‫א‬‫א‬
‫א‬‫א‬‫א‬،‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬
 ‫א‬‫א‬
‫א‬‫א‬،‫א‬‫א‬
‫א‬F‫א‬‫א‬‫א‬K‫א‬
 K‫א‬E‫א‬‫א‬
- ٦١ -
 ‫א‬‫א‬‫א‬  ١٤٠  ‫א‬
 ‫א‬‫א‬‫א‬  ‫א‬‫א‬ ‫א‬
 ‫א‬‫א‬‫א‬3J 4
 ‫א‬‫א‬‫א‬‫א‬‫א‬ ‫א‬
 W
 E‫א‬‫א‬F‫א‬‫א‬‫א‬‫א‬‫ א‬.١
‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬
 K‫א‬‫א‬‫א‬
Cl2
CH3CH3 CH3CH2CI + HCI + ...
UV or heat
‫ﺿﻮ او ﺣﺮارة‬
Br2
CH3 - CH = CH2 CH2 - CH = CH2 + HBr
UV or
Br
 ‫א‬‫א‬‫א‬‫א‬ .٢
‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬
 W‫א‬‫א‬
HCl
CH3 - CH = CH2 CH3 - CH - CH3
CCl4
Cl
‫א‬‫א‬
 W‫א‬‫א‬
HBr
CH3-CH = CH2 R-O-O-R CH3CH2CH2
Br
 
- ٦٢ -
 ‫א‬‫א‬‫א‬  ١٤٠  ‫א‬
 ‫א‬‫א‬‫א‬  ‫א‬‫א‬ ‫א‬
 W‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬
HCl HCl
CH CH CH2 = CH CH3CHCl2
CCl4 CCl4
Cl
 E‫א‬‫א‬F‫א‬‫א‬‫א‬‫ א‬.٣
‫א‬HX
 ‫א‬‫א‬‫א‬ ‫א‬‫א‬
 W‫א‬EPCl5 , PCl3 , PBr3F‫א‬‫א‬SOCl2‫א‬

HCl
CH3(CH2)5 CH2OH CH3(CH2)5 CH2 +H2O
ZnCl2 / 150ْ
Cl
NR 3
CH3CH2OH + SOCl 2 CH3CH2Cl + SO 2 + HCl
CH3CH2OH +PBr3 CH3CH2Br + P (OH)3


 ‫א‬‫א‬5J 4
‫א‬‫א‬‫א‬‫א‬‫א‬
 ‫א‬
‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬KE‫א‬F‫א‬‫א‬
KE‫א‬F‫א‬
 KKKK‫א‬‫א‬
 Nucleophilic substitution reactions‫א‬‫א‬‫א‬ K١


  ‫א‬
 ‫א‬‫א‬‫א‬
E‫א‬‫א‬‫א‬F‫א‬‫א‬
- ٦٣ -
 ‫א‬‫א‬‫א‬  ١٤٠  ‫א‬
 ‫א‬‫א‬‫א‬  ‫א‬‫א‬ ‫א‬
‫א‬‫א‬، ‫א‬‫א‬‫א‬‫א‬‫א‬
 W‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬
R3Cδ+χδ- R3C-Nu + χ –
 W‫א‬‫א‬‫א‬‫א‬
O
- - - -
SR , SH , CH3NH2 , NH3 , - O - C - R , OR ,OH
.. - -
N (CH3) 3 , HN (CH3)2 , CN ,R - C = C

‫א‬،‫א‬‫א‬‫א‬‫א‬
 W‫א‬‫א‬

KOH
CH3CH2CH2Br CH3CH2CH2OH
H2 O
Elemination reactionsEEFE‫א‬‫א‬F‫א‬ K٢
‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬
 ‫א‬
 K‫א‬‫א‬E‫א‬‫א‬‫א‬‫א‬F‫א‬
- +
_ KOH (Or) CH3CH2O Na
CH3CH CH3 CH3 - CH = CH2
EtOH /
Br
- ٦٤ -
 ‫א‬‫א‬‫א‬  ١٤٠  ‫א‬
 ‫א‬‫א‬‫א‬  ‫א‬‫א‬ ‫א‬
-4‫א‬‫א‬ K٣
Grignard formation K
 K‫א‬‫א‬‫א‬‫א‬‫א‬
ether
CH3CH2CH2Br + Mg CH3CH2CH2MgBr
 ‫א‬ ‫א‬          
 K،‫א‬‫א‬‫א‬‫א‬‫א‬
 ‫א‬ K
W‫א‬‫א‬
- +
CH3CH2CH2Br + 2Li CH3CH2CH2 Li + LiBr
 K‫א‬‫א‬‫א‬‫א‬‫א‬
 ‫א‬‫א‬‫א‬٤J ٦
‫א‬‫א‬‫א‬‫א‬‫א‬
 KD.D.T.‫א‬
H
Cl C Cl
CCl 3
 D.D.T

‫א‬‫א‬‫א‬–[CF2–CF2]nTeflonW‫א‬
‫א‬–[H2–CCl2]n–‫א‬‫א‬‫א‬‫א‬‫א‬
K‫א‬‫א‬‫א‬‫א‬–[CH2 – CHCl2-]n–PVC K‫א‬
- ٦٥ -
 ‫א‬‫א‬‫א‬  ١٤٠  ‫א‬
 ‫א‬‫א‬‫א‬  ‫א‬‫א‬ ‫א‬
CCl3FCCl2F2‫א‬CF3CHClBr‫א‬HCX3haloform‫א‬
‫א‬‫א‬‫א‬،‫א‬‫א‬‫א‬
‫א‬‫א‬‫א‬K‫א‬‫א‬‫א‬
 Antifungus‫א‬Antibiotics‫א‬‫א‬‫א‬

 ٤J ٧
 EIUPAC F‫א‬‫א‬‫א‬‫א‬W١

Br
CH3CH_ CH _ CH3
E E
 Br CH3

NO2
_ _ _
CH CH3  E CH 3 CH2 CH=CH 2 E
Cl  Cl

 

CH2 = CH CH2Cl E

 E3◦ 2◦1◦F‫א‬‫א‬‫א‬W٢

Br
CH3 Cl CH3
CH3 C CH3 E E E
 Cl  

 K‫א‬‫א‬‫א‬‫א‬W٣

CH3
HCl E
CH3CHOH ZnCl
2
HBr
CH 3 E
- ٦٦ -
 ‫א‬‫א‬‫א‬  ١٤٠  ‫א‬
 ‫א‬‫א‬‫א‬  ‫א‬‫א‬ ‫א‬
CH3
Br2 E
CH3CHCH3 hv
Cl2
CH2CH3 hv
SOCl2
OH E
+ -
_ CH Na O CH2CH3
CH3CH2CH 3 CH3CH2OH E
Br
Br
KOH
CH3 C CH2
EtOH
CH3
NH2CH3 E
CH 3CH 2CH 2Cl
- +
CH3C C Na
CH 2CH2Br E
KOH
CH 3CH _ CH 3 E
EtOH /
Br
ether E
CH 3CH 2CH 2Br + Mg

 W‫א‬‫א‬‫א‬‫א‬W٤

-
OH  E١
CH 3CHBrCH 3 ethanol
-
OH  E٢
CH 3CHBrCH 3 H2O
-
CN  E٣
(CH 3)3CBr
ethanol
H2 O  E٤
(CH 3)3CBr




- ٦٧ -
 ‫א‬‫א‬‫א‬  ١٤٠  ‫א‬
 ‫א‬‫א‬‫א‬  ‫א‬‫א‬ ‫א‬
 ٤J ٧

 W١
2-Bromo-3-methyl butane–
1-Bromo-2-Nitro cyclohexaneJ 
1-chloro-1-buteneJ 

 W٢
3◦ E 2◦ E  1◦ E


 W٣
CH3 CH3
HCl
CH3CHCl + H2O
E
CH3CHOH ZnCl
2
CH3 CH3
Br2
CH3CHCH3 hv CH3 C CH3 E
Br
NH2CH3 E
CH3CH2CH2Cl CH3CH2CH2NHCH 3
KOH
CH CH_ CH
3 3 EtOH / CH 3CH=CH 2 + HBr E
Br

 W٤
‫א‬‫א‬J ١
‫א‬‫א‬J ٢
‫א‬‫א‬J ٤


- ٦٨ -
 ‫א‬‫א‬‫א‬
‫א‬‫א‬‫א‬‫א‬
‫ א‬‫א‬
‫א‬
‫א‬‫א‬
‫א‬‫א‬
٥
‫א‬‫א‬ ١٤٠ ‫א‬
‫א‬‫א‬ ‫א‬‫א‬ ‫א‬
 W‫א‬‫א‬
‫א‬‫א‬‫א‬ ‫א‬‫א‬ 
 ‫א‬‫א‬‫א‬
 K‫א‬‫א‬‫א‬

 W‫א‬‫א‬
 W‫א‬‫א‬‫א‬
 K‫א‬‫א‬ .١
 K‫א‬‫א‬‫א‬‫א‬ .٢
K‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬ .٣

 W‫א‬‫א‬‫א‬
 K٪80‫א‬‫א‬‫א‬
 KW‫א‬‫א‬

 W‫א‬‫א‬
 KOverhead Projector .١
 K‫א‬‫א‬‫א‬ .٢
K .٣

 W‫א‬‫א‬
 K‫א‬‫א‬‫א‬‫א‬
- ٦٩ -
‫א‬‫א‬ ١٤٠ ‫א‬
‫א‬‫א‬ ‫א‬‫א‬ ‫א‬
 W5J 1
J OH‫א‬‫א‬ 
‫א‬‫א‬‫א‬،ArOH‫א‬‫א‬،ROH‫א‬‫א‬‫א‬
 Ar 
 ‫א‬R،ArR‫א‬‫א‬
،SP3‫א‬‫א‬‫א‬،
KSP2‫א‬‫א‬
‫א‬‫א‬‫א‬ ،‫א‬‫א‬‫א‬
‫א‬ ‫א‬‫א‬K‫א‬
‫א‬K‫א‬‫א‬
 K‫א‬
 W‫א‬5J 2
‫א‬
 ‫א‬‫א‬‫א‬‫א‬
 W‫א‬‫א‬‫א‬،‫א‬‫א‬‫א‬‫א‬

  
O O
Tertiary 3 Secondary 2 Primary 1O
H R H
R C OH R C OH R C OH
R R H
 ‫א‬ ‫א‬   ‫א‬ ‫א‬   ‫א‬ ‫א‬ 
  J OH   J OH   J OH 
 ‫א‬       
     K‫א‬ KR‫א‬
K‫א‬
- ٧٠ -
‫א‬‫א‬ ١٤٠ ‫א‬
‫א‬‫א‬ ‫א‬‫א‬ ‫א‬
 W‫א‬5J 3
‫א‬KIUPAC‫א‬‫א‬‫א‬‫א‬،
 K‫א‬‫א‬‫א‬‫א‬
 W‫א‬‫ א‬K١
 W‫א‬‫א‬‫א‬‫א‬

CH3 OH  CH3CH2OH  CH2=CH-CH2OH
 Methyl alcohl  Ethyl alcohol  Allyl alcohol
CH3
CH3 CH CH3
CH3 c CH3
OH
OH
Isopropyl alcohol Tert-Butyl alcohol
OH CH2OH
Cyclopentyl alcohol Benzyl alcohol


 WE‫א‬FW‫א‬‫ א‬K٢
J OH‫א‬‫א‬ K١
EeF‫א‬‫א‬‫א‬‫א‬ ‫א‬
 WKJ ol
CH3OH
 CH3CH2OH
- ٧١ -
‫א‬‫א‬ ١٤٠ ‫א‬
‫א‬‫א‬ ‫א‬‫א‬ ‫א‬
Ethanol Methanol
-OH‫א‬‫א‬‫א‬‫א‬ K٢
‫א‬‫א‬‫א‬،‫א‬‫א‬‫א‬‫א‬
 W‫א‬‫א‬‫א‬E١F‫א‬‫א‬‫א‬

CH3CH2CH2CH CH3
CH3CH2CH2OH
OH
1-Propanol 2-Pentanol
C 2H 5
OH
CH3CH2CHCH2CHCH3
OH
Cyclohexanol 4-Ethyl-2-hexanol
CH2CH2Br
CH3CH2CH2CHCH2 OH
2-(2-Bromoethyl)-1-Pentanol

‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬ K٣
‫א‬K‫א‬‫א‬‫א‬‫א‬‫א‬
‫א‬‫א‬‫א‬‫א‬‫א‬
 ‫א‬‫א‬‫א‬‫א‬‫א‬
 K‫א‬
CH2CH3
CH2 CH CH CH CH3
CH3CH C CH2
OH CH3
OH
4-Methyl-1-Penten-3-ol 3-Ethyl-3-buten-2-ol
OH
CH C CH CH3
OH
CH3
3-Butyn-2-ol  4-Methyl-2-cyclohexenol
- ٧٢ -
‫א‬‫א‬ ١٤٠ ‫א‬
‫א‬‫א‬ ‫א‬‫א‬ ‫א‬
 -ol  ‫א‬tetra,tri ,di‫א‬‫א‬‫א‬ K٤

 KK‫א‬


CH2 CH2 CH2 CH CH2
OH OH OH OH OH
 1,2-Ethanediol 1,2,3-Propantriol
 Ethylene glycol Glycerol or Glycerene
 W‫א‬
   ‫א‬  ‫א‬     ‫א‬   
،‫א‬ -OH ،
،‫א‬‫א‬‫א‬
 W‫א‬‫א‬
OH OH
OH
Br NH2
Phenol m-Bromophenol p-Aminophenol
OH
OH
COOH
OH
o-Hydroxybenzoic acid (
Salicylic acid)
Hydroquinone
- ٧٣ -
‫א‬‫א‬ ١٤٠ ‫א‬
‫א‬‫א‬ ‫א‬‫א‬ ‫א‬
 W‫א‬‫א‬‫א‬‫א‬5J 4
‫א‬‫א‬،‫א‬‫א‬‫א‬
‫א‬ ‫א‬  ‫א‬ ‫א‬     ‫א‬   
‫א‬‫א‬‫א‬‫א‬‫א‬K‫א‬
 K‫א‬‫א‬،EF‫א‬‫א‬
R Ar
Ar
O O
O O
H
R H H
H

 ‫א‬
‫א‬‫א‬‫א‬‫א‬
 K‫א‬‫א‬‫א‬
Ethanol Propane
 L٤٦  °٧٨ ‫א‬‫א‬
L٤٤  °٤٢ ‫א‬
،‫א‬ ‫א‬،‫א‬‫א‬‫א‬‫א‬
‫א‬‫א‬،‫א‬‫א‬‫א‬‫א‬
،‫א‬‫א‬‫א‬‫א‬،‫א‬‫א‬‫א‬
 K‫א‬
H R
o o o
R H
H H

 ‫א‬
- ٧٤ -
‫א‬‫א‬ ١٤٠ ‫א‬
‫א‬‫א‬ ‫א‬‫א‬ ‫א‬
 W‫א‬‫א‬5J 5
 W‫א‬ K 
،‫א‬‫א‬‫א‬‫א‬‫א‬
 K‫א‬
H
+
H
CH3CH CH2 + H2 O CH3 CH CH3
Propene  2-Propanol
‫א‬،Ethanol‫א‬Methanol  ‫א‬‫א‬
 W
  water gas‫א‬‫א‬‫א‬‫א‬W‫א‬ K

 KE‫א‬‫א‬ F
O
1300 C
C +H2O CO + H2
‫א‬‫א‬‫א‬Water gas
 K300 atm300c ‫א‬
Zn + Cr 2 O3 as Cat.
CO + H 2 + H2 CH3OH
Water gas
 WNatural gas‫א‬‫א‬ K

‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬
 K900 Co
Ni as Cat.
CH4 + H2O CO + 3H 2O
 K‫א‬‫א‬‫א‬Synthesis‫א‬‫א‬‫א‬
ZnO + Cr 2 O3 as Cat.
CO + H 2O O CH3OH
300C , 300 atm.
- ٧٥ -
‫א‬‫א‬ ١٤٠ ‫א‬
‫א‬‫א‬ ‫א‬‫א‬ ‫א‬
 W‫א‬‫א‬
        ‫א‬  K 
: Ethyl hydrogen sulphate٨٠Co‫א‬
CH2 CH2 + H2SO4 CH3 CH2 O SO2 OH
 K‫א‬
CH3 CH2 O SO2 OH + H2O CH3 CH2 OH + H2SO4
 ‫א‬ ‫א‬ ‫א‬   ‫א‬ ‫א‬  K
Phosphoric F‫א‬‫א‬
Co‫א‬E‫א‬‫א‬acid on silca
 K70 atm٣٠٠
 W‫א‬ K 
‫א‬‫א‬‫א‬‫א‬
 K‫א‬‫א‬‫א‬‫א‬
SO3H - + OH
ONa
NaOH
HCl
Benzene sulfonic acid Sodium phenoxide Phenol
 W‫א‬‫א‬
،Propene ‫א‬‫א‬‫א‬‫א‬، Cumene‫א‬ E١
AlCl3‫א‬‫א‬‫א‬‫א‬
 K‫א‬‫א‬
 K‫א‬‫א‬
CH CH3
+ CH3 CH CH2
CH3
Cumene
- ٧٦ -
‫א‬‫א‬ ١٤٠ ‫א‬
‫א‬‫א‬ ‫א‬‫א‬ ‫א‬
‫א‬‫א‬Hydroperoxide ‫א‬‫א‬‫א‬‫א‬
 K‫א‬‫א‬‫א‬‫א‬‫א‬
CH3
OH
CH CH3 C CH3 +
H
+ O2 + ( CH3 )2 C O
CH3 O OH
Phenol Acetone

 K‫א‬‫א‬‫א‬‫א‬
 W‫א‬‫א‬ E٢
- +
Cl O Na
Cl2 + OH
NaOH
H
o o
40 C 330 C
Benzene Chlorobezene Sodium phenoxide Phenol
 W‫א‬‫א‬5J 6
 W‫א‬‫א‬
 W‫א‬‫א‬‫א‬‫א‬‫א‬‫ א‬-١
‫א‬ ،‫א‬‫א‬‫א‬‫א‬
 K‫א‬‫א‬‫א‬‫א‬،‫א‬
H2SO4
2CH3CH2OH O
(CH3CH2) 2 + H2O
140 C
Ethanol Diethyl ether
H2SO4
CH3CH2OH O
CH2 CH2 + H2O
180 C
Ethylene
 K‫א‬‫א‬‫א‬‫א‬‫א‬
- ٧٧ -
‫א‬‫א‬ ١٤٠ ‫א‬
‫א‬‫א‬ ‫א‬‫א‬ ‫א‬
 W Oxidation‫א‬
،‫א‬‫א‬‫א‬ E1 F‫א‬‫א‬
‫א‬‫א‬K‫א‬‫א‬‫א‬‫א‬‫א‬
 W‫א‬‫א‬،‫א‬
Cu/
CH3CH2OH CrO3 or Pyridine
CH3CHO
O
Ethanol (1) Acetaldehyde
3+
H2Cr2O7
CH3CH2OH CH3COOH + Cr
Acetic acid
OH O
H2Cr2O7
CH3CHCH3 CH3 C CH3
or Cu /
o
Alcohol ( 2 ) Ketone
O 
Oxid.Agent
CH3-C-CH3 
CH3
W‫א‬‫ א‬-٢
‫א‬‫א‬‫א‬‫א‬
،‫א‬‫א‬‫א‬‫א‬
 K‫א‬
- +
CH3 OH + Na CH3 O Na + 12 H2
Methanol Sodium Methoxide
- +
OH O Na
+ Na + 12 H2
Phenol
- ٧٨ -
‫א‬‫א‬ ١٤٠ ‫א‬
‫א‬‫א‬ ‫א‬‫א‬ ‫א‬
 W‫א‬‫א‬ -٣
K‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬
 K‫א‬ H+‫א‬
O
+
H
(Ar)R OH + RCOOH (Ar)RO C R + H2 O
Alcohol or Phenol Ester
+
H
CH3COOH + CH3CH2OH CH3COOCH2CH3 + H2O
Acetic acid Ethyl alcohol Ethyl acetate
- ٧٩ -
‫א‬‫א‬ ١٤٠ ‫א‬
‫א‬‫א‬ ‫א‬‫א‬ ‫א‬
 E‫א‬‫א‬F
 WE3 FE2 FE1 F‫א‬‫א‬‫א‬‫א‬ E١
CH3 CH2 CH2 OH CH2CH3 (A
(B
CH3 CH2 C OH
CH2CH3

Br (D CH3 (C
CH3 CH CH2 H2 C C CH2 OH
OH
 W‫א‬‫א‬ E٢
(A (B OH (c (D
OH OH
CH2OH CH3 CH 3
Br OH
NH2 CH3
 OH
 W‫א‬‫א‬ E٣
(A
CH3 CH CH2CH3 CH3 C CH2CH3
OH O

(B
O
+
H
CH3 CH2 C OH + CH3OH

CH3 CH2 CH2 OH Cu , ? (C

H2SO4 ? (D
OH + K2Cr2O7
OH
(E

- ٨٠ -
‫א‬‫א‬ ١٤٠ ‫א‬
‫א‬‫א‬ ‫א‬‫א‬ ‫א‬
 W‫א‬‫א‬‫א‬‫א‬ E٤
1) 2,4-Dimethyl-2-Octanol.
2) Cyclopentane-1,4-diol.
3) 2,2,2-Trichloroethanol.
4) 2-Butene-1,4-diol.
5) 3-Bromo-2-nonanol.
6) O- Bromophenol.
7) 2,4,6-Trichlorophenol
8) p-Hydroxybenzyl alcohol.










- ٨١ -
‫א‬‫א‬ ١٤٠ ‫א‬
‫א‬‫א‬ ‫א‬‫א‬ ‫א‬
 E‫א‬‫א‬F
 WE1F‫א‬‫א‬
 K3o،  1,1-Diethyl propanol EA
. 2o، 1-Bromo-2-propanol (D
 WE2F‫א‬‫א‬
 4-Amino-5-bromo phenol EA
2,4,6-Trimethyl phenol EC
 WE3F‫א‬‫א‬
KMnO 4 (A
H2O

O
(B
CH3 CH2 C O CH 3

O
CH3 CH2 C H (C

 WE4F‫א‬‫א‬
CH3
CH3-CH2-CH2-CH2-C-CH2-CH-CH3 (1
CH3 OH

CCl3-CH2-OH (3
CH3-CH2-CH2-CH2-CH2-CH2-CH-CH-CH3 (5
Br OH

OH
Cl Cl (7
Cl


- ٨٢ -
 ‫א‬‫א‬‫א‬
‫א‬‫א‬‫א‬‫א‬
‫ א‬‫א‬
‫א‬
‫א‬‫א‬
‫א‬‫א‬
٦
 ‫א‬‫א‬ ١٤٠ ‫א‬
‫א‬‫א‬ ‫א‬‫א‬ ‫א‬
 W‫א‬‫א‬
 K‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬

 W‫א‬‫א‬
 W‫א‬‫א‬‫א‬
 K‫א‬‫א‬ .١
K‫א‬‫א‬‫א‬‫א‬ .٢

 W‫א‬‫א‬‫א‬
 K٪80‫א‬‫א‬‫א‬

 W‫א‬‫א‬
 K

 W‫א‬‫א‬
 KOverhead Projector .١
K .٢

 W‫א‬‫א‬
 K‫א‬‫א‬‫א‬‫א‬

- ٨٣ -
 ‫א‬‫א‬ ١٤٠ ‫א‬
‫א‬‫א‬ ‫א‬‫א‬ ‫א‬
 W6J 1
 R/RR-O-R/‫א‬‫א‬‫א‬‫א‬ 
 WK
‫א‬‫א‬‫א‬،R/ R‫א‬‫א‬
 K‫א‬
 W‫א‬‫א‬6J 2
‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬ 
 ‫א‬‫א‬،Ether
 ‫א‬
 K‫א‬
CH3OCH2CH3 CH3CH2OCH2CH3 CH3OCH3
Ethyl ether Methyl ether
Ethyl methyl ether
o CH3 o
Methyl phenyl ether Phenyl ether
( Anizole )
-O-R،IUPAC ‫א‬‫א‬‫א‬‫א‬
‫א‬،‫א‬REAlkoxy)‫א‬
 W‫א‬‫א‬R(Aryloxy)
CH3CH2CHCH3
Br o CH2CH3
p-Bromophenoxy ethane
oCH3
2-Methoxy butane
o CH2 CH3
 Ethoxy cyclohexane
‫א‬‫א‬‫א‬oxa‫א‬
 W‫א‬‫א‬‫א‬‫א‬ K‫א‬
- ٨٤ -
 ‫א‬‫א‬ ١٤٠ ‫א‬
‫א‬‫א‬ ‫א‬‫א‬ ‫א‬
1 2 3 4 5 6 7 8 9
CH2 O CH2 CH2 O CH2 CH2 CH3
O
Cl
1-Chloro-2,5,8 -trioxanonane
 W‫א‬‫א‬
o o O
Oxlane Oxane 1,4-Dioxane
or or or
Tetrahydrofuran Tetrahydropyran 1,4-Dioxa cyclohexane
( THF )
o
o
CH2 CH2
Oxetane
Oxiran e cepoxide
or
or Trimethylene oxide
Ethylene oxide

 W‫א‬‫א‬‫א‬‫א‬
‫א‬‫א‬
 ،‫א‬‫א‬
K‫א‬‫א‬ ‫א‬‫א‬‫א‬،‫א‬‫א‬‫א‬،‫א‬
‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬
 K‫א‬
‫א‬،‫א‬،‫א‬‫א‬‫א‬‫א‬ 
‫א‬،‫א‬‫א‬ ،‫א‬‫א‬‫א‬‫א‬K‫א‬
 W‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬
- ٨٥ -
 ‫א‬‫א‬ ١٤٠ ‫א‬
‫א‬‫א‬ ‫א‬‫א‬ ‫א‬
R
O H
O R
R
H O
R


 W‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬
‫א‬ ‫א‬ ‫א‬‫א‬ ‫א‬ ‫א‬
 o78  46 Ethanol CH3CH2OH
   o24J 46 Methylether CH3OCH3
  o42J 44 Propane CH3CH2CH3
 W‫א‬‫א‬‫א‬6J 3
‫א‬‫א‬F‫א‬‫א‬‫א‬ 
،‫א‬‫א‬‫א‬E‫א‬ ‫א‬‫א‬
 K
‫א‬‫א‬‫א‬‫א‬‫א‬
‫א‬EPeroxide)‫א‬ (‫א‬‫א‬‫א‬F
 K
‫א‬‫א‬‫א‬‫א‬
،Fe+++‫א‬‫א‬،‫א‬‫א‬‫א‬‫א‬‫א‬ FeSO4
 W‫א‬‫א‬ ‫א‬‫א‬
- ٨٦ -
 ‫א‬‫א‬ ١٤٠ ‫א‬
‫א‬‫א‬ ‫א‬‫א‬ ‫א‬

-
+++ SCN
Peroxide + Fe Fe(SCN)3
 
 W‫א‬‫א‬‫א‬‫א‬‫א‬
‫א‬F‫א‬‫א‬ .١
 KE‫א‬‫א‬
K‫א‬‫א‬‫ א‬.٢
K ‫א‬‫א‬‫א‬‫א‬‫ א‬.٣
 W‫א‬‫א‬6J 4
 W‫א‬‫א‬‫א‬W
‫א‬‫א‬‫א‬W
 ‫א‬‫א‬‫א‬‫ א‬.١
‫א‬‫א‬‫א‬K ‫א‬‫א‬
 K‫א‬‫א‬
H2SO4
CH3CH2OH CH3CH2OCH2CH3
140
 W .٢
‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬ 
F‫א‬‫א‬،Ealkoxide ion‫א‬F‫א‬
 K‫א‬‫א‬‫א‬Ephenoxide ion‫א‬
- +
CH3 CH O Na + CH3CH2Br CH3 CH O CH2CH3
CH3 CH3
Ethyl isopropyl ether
- ٨٧ -
 ‫א‬‫א‬ ١٤٠ ‫א‬
‫א‬‫א‬ ‫א‬‫א‬ ‫א‬
- +
O Na O CH3
+ CH3Br
Anizole
 W‫א‬‫א‬‫א‬W
W‫א‬‫א‬‫א‬‫ א‬.١
 K‫א‬‫א‬‫א‬‫א‬
W‫א‬Diethyl ether .٢
‫א‬‫א‬‫א‬‫א‬
 K‫א‬‫א‬
 W‫א‬‫א‬6J 5
‫א‬ ‫א‬‫א‬‫א‬‫א‬،‫א‬‫א‬‫א‬
 K‫א‬‫א‬‫א‬‫א‬،
+
H
CH3 CH 2 O CH 2 CH 3 + 2HI 2CH3 CH 2-I + H 2O
 Iodoethane







- ٨٨ -
 ‫א‬‫א‬ ١٤٠ ‫א‬
‫א‬‫א‬ ‫א‬‫א‬ ‫א‬
 E‫א‬‫א‬F
 W‫א‬‫א‬ .١
C6H5CH2 O C3 H7 CH3CH2CH2OCH2CH3E1
E4
CH3 CH CH2 CH CH3 (5 (CH3CH2CH2CH2)2OE2
CH3 O CH2CH3
CH3 O CH CH3 (3
(6
CH3
O CH2 CH3
 W‫א‬‫א‬‫א‬‫ א‬.٢
1) Diisopropyl ether. 2) Diallyl ether.
3) tert-Butyl methyl ether. 4) Benzyl ether.
5) Phenyl ether. 6) 4-Ethoxy -2-Methylhexane.
 W‫א‬‫א‬‫א‬‫א‬‫א‬‫ א‬.٣
CH3
(1) + (2) CH3 C O CH2 (1
CH3
O-
CH3O + (CH3)3CBr (3) (2

-
O
(CH3)C O + CH3I (4) (3


HI acid conc.
(CH 3)2CHCH 2OC(CH 3)3 (5) (4
with
- ٨٩ -
 ‫א‬‫א‬ ١٤٠ ‫א‬
‫א‬‫א‬ ‫א‬‫א‬ ‫א‬
 K‫א؟‬‫א‬‫א‬ .٤
CH3CH2CHCH2CH2CH3 (2  CH3CH2CH2CH2CH2CH2CH3 (1
OH
 CH3CH2CH2 O CH2CH2CH3 (3























- ٩٠ -
 ‫א‬‫א‬ ١٤٠ ‫א‬
‫א‬‫א‬ ‫א‬‫א‬ ‫א‬

 E‫א‬‫א‬F
WE1F‫א‬‫א‬
Dibutyl ether (3 Ethyl propyl ether (1
Isopropyl methyl ether (5
 WE2F‫א‬‫א‬
CH 3 O C (CH 3)3 (2 (CH 3)2 CH O CH (CH 3)2 (1
CH3-CH-CH 2-CH 2-CH-CH 3 (6
CH3 O C2H5
 WE3F‫א‬‫א‬
(CH3)3 C O CH 3 (2
(CH3)3 C O CH 3 (3


- ٩١ -
 ‫א‬‫א‬‫א‬
‫א‬‫א‬‫א‬‫א‬
‫א‬‫א‬
 ‫א‬‫א‬‫א‬
 ‫א‬‫א‬‫א‬
٧
 ‫א‬‫א‬ ١٤٠ ‫א‬
‫א‬‫א‬‫א‬ ‫א‬‫א‬ ‫א‬
 W‫א‬‫א‬
‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬
 K‫א‬‫א‬‫א‬‫א‬
 W‫א‬‫א‬
 W‫א‬‫א‬‫א‬
 K‫א‬‫א‬‫א‬ .١
 K‫א‬‫א‬‫א‬‫ א‬.٢
 K‫א‬‫א‬‫א‬‫א‬‫א‬ .٣
 W‫א‬‫א‬‫א‬
 K٪80‫א‬‫א‬‫א‬

 W‫א‬‫א‬
 K
 W‫א‬‫א‬
 KOverhead Projector  .١
 K‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬ .٢
 W‫א‬‫א‬
 K‫א‬‫א‬‫א‬‫א‬




- ٩٢ -
 ‫א‬‫א‬ ١٤٠ ‫א‬
‫א‬‫א‬‫א‬ ‫א‬‫א‬ ‫א‬
 W7J 1
‫א‬K C=O ‫א‬‫א‬‫א‬‫א‬
O
EArF،R R(Ar)-C-H W

  ‫א‬‫א‬
O
 R , R  R
C R
W ‫א‬‫א‬‫א‬K
 K
 W‫א‬‫א‬‫א‬7J 2
 KIUPAC‫א‬‫א‬‫א‬‫א‬،‫א‬‫א‬‫א‬
 W‫א‬‫א‬
 W‫א‬‫א‬J  
J ic acid‫א‬‫א‬‫א‬‫א‬  ‫א‬‫א‬‫א‬
‫א‬‫א‬aldehydeE‫א‬‫א‬  ‫א‬F
 K‫א‬

O
 ‫א‬‫א‬ Formic acid
H C H
 Formaldehyde
O
 ‫א‬‫א‬
CH 3 C H  Acetic acid
 Acetaldehyde
 ‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬
(C C C C O)

- ٩٣ -
 ‫א‬‫א‬ ١٤٠ ‫א‬
‫א‬‫א‬‫א‬ ‫א‬‫א‬ ‫א‬
‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬
 ‫א‬
 W‫א‬‫א‬
CH2CH3 O
CH3 CH CH C H
B
CH3

Dimethyl Valeraldehyde
 W‫א‬J  
F‫א‬‫א‬‫א‬‫א‬‫א‬ 
 Wketone‫א‬E‫א‬‫א‬
O O
CH3 C CH3 CH3 C CH( CH3)2

Dimethyl ketone Methyl isopropyl ketone

 ( acetone )
 Phenyl ‫א‬‫א‬‫א‬phenone‫א‬
 W‫א‬‫א‬‫א‬‫א‬‫א‬E-oic acid F-ic acid
O O
C CH3 C
 Acetophenone  Benzophenone
 W‫א‬‫א‬
 W‫א‬‫א‬J  
،‫א‬‫א‬J al‫א‬‫א‬‫א‬J e ‫א‬‫א‬‫א‬
– KK ‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬
‫א‬‫א‬‫א‬K‫א‬‫א‬‫א‬
 W‫א‬‫א‬
- ٩٤ -
 ‫א‬‫א‬ ١٤٠ ‫א‬
‫א‬‫א‬‫א‬ ‫א‬‫א‬ ‫א‬
O CH3 O
CH3 C H CH3 CH CH2 C H

 Ethanol
 3-Methyl butanal
‫א‬‫א‬‫א‬
 K‫א‬
O O
C H
C H
 Benzaldehyde CH 3
 p-tolualdehyde
 W‫א‬–
‫א‬‫א‬‫א‬‫א‬‫א‬
‫א‬J e‫א‬EJ al FJ one ‫א‬،‫א‬
‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬K‫א‬‫א‬
‫א‬‫א‬IUPAC‫א‬‫א‬‫א‬
 K‫א‬‫א‬‫א‬
O O O
CH3 C CH3 CH2 CH C CH3

Propanone 3-buten-2-one
Cyclopentanone
 W‫א‬‫א‬‫א‬‫א‬‫א‬7J 3
‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬
+ -
 ‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬ C=O
‫א‬‫א‬‫א‬‫א‬‫א‬،‫א‬‫א‬
‫א‬‫א‬‫א‬‫א‬،‫א‬‫א‬
- ٩٥ -
 ‫א‬‫א‬ ١٤٠ ‫א‬
‫א‬‫א‬‫א‬ ‫א‬‫א‬ ‫א‬
‫א‬ ‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬K
 K‫א‬
O
C O H H

 ‫א‬
 W‫א‬‫א‬‫א‬‫א‬‫א‬
Formalin‫א‬،‫א‬‫א‬‫א‬‫א‬
‫א‬K‫א‬‫א‬،E٪37F
،‫א‬، ‫א‬‫א‬‫א‬‫א‬‫א‬K‫א‬‫א‬
‫א‬،‫א‬‫א‬،56
 K‫א‬‫א‬
 W‫א‬‫א‬‫א‬7J 4
 W‫א‬‫א‬‫א‬‫א‬–
 W‫א‬ K 
،‫א‬‫א‬‫א‬‫א‬‫א‬
 ‫א‬‫א‬‫א‬K‫א‬
O
Cu /
CH3CH2CH2OH CH3CH 2C H
o
1-Propanol (1) Propanal

OH O
+3
H2Cr 2O7
CH3CHCH 3 CH3C CH3 + Cr
o
2-Propanol (2) Acetone

 W‫א‬‫א‬ K 
- ٩٦ -
 ‫א‬‫א‬ ١٤٠ ‫א‬
‫א‬‫א‬‫א‬ ‫א‬‫א‬ ‫א‬
‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬
 ‫א‬‫א‬E
 
 ‫א‬F‫א‬
 W‫א‬‫א‬‫א‬
O O
AlCl3
+ CH3CH2C Cl C CH2CH3 + HCl
 Ethyl phenyl ketone
 K‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬
 W‫א‬‫א‬‫א‬‫א‬J  
 W‫א‬‫א‬‫א‬ K١
‫א‬‫א‬‫א‬‫א‬‫א‬
 W‫א‬‫א‬
O (1
CuO-Ag
2CH 3OH + O2 O 2H C H + 2H 2O
 500-650 C
O
(2
PdCl2
CH2 CH2 + 1/2 O2 CH3 C H
H 2O

 W‫א‬‫א‬ K٢
 K‫א‬500 CO‫א‬‫א‬2-propanol‫א‬‫א‬
O
Cu as Cat.
(CH3)2CHOH O
CH3 C CH3
500 C
2-Propanol Acetone

 W‫א‬‫א‬‫א‬7J 5
، ‫א‬‫א‬‫א‬‫א‬ 
‫א‬‫א‬‫א‬‫א‬K‫א‬
- ٩٧ -
 ‫א‬‫א‬ ١٤٠ ‫א‬
‫א‬‫א‬‫א‬ ‫א‬‫א‬ ‫א‬
‫א‬EF‫א‬،‫א‬
 W‫א‬‫א‬‫א‬‫א‬
 .(Cyanohydrine )HCN‫א‬ .١
O OH
-
CN
CH3 C H + HCN CH3 C H
CN
 Acetaldehyde cyanohydrine
O
- OH
CN
CH3 C CH3 + HCN CH3 C CH3
CN
Acetone cyanohydrine

 W‫א‬‫ א‬.٢
‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬
 WG-NH2
O
 NH Ar  OH  H=G
C NH 2 
 NH
‫א‬‫א‬‫א‬
‫א‬‫א‬‫א‬‫א‬K‫א‬‫א‬
‫א‬‫א‬K‫א‬‫א‬‫א‬
F ‫א‬‫א‬‫א‬
 
 K‫א‬‫א‬‫א‬ E‫א‬
O
+ CH 3
H
CH 3 C CH 3 + NHNH 2 C N NH
CH 3
 Acetone Phenylhydrazene
- ٩٨ -
 ‫א‬‫א‬ ١٤٠ ‫א‬
‫א‬‫א‬‫א‬ ‫א‬‫א‬ ‫א‬
 WReduction‫א‬‫ א‬.٣
‫א‬‫א‬ ‫א‬‫א‬‫א‬‫א‬‫א‬ 
 KNaBH4‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬
OH
O H2/Pt
CH 3 CH CH 3
CH3 C CH 3
1)NaBH 4
CH 3 CH CH 3
2)H 2 O
OH
 2-Propanol
 WOxidation‫ א‬.٤
‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬ 
 K‫א‬
O O
(O)
R C H R C OH


  





- ٩٩ -
 ‫א‬‫א‬ ١٤٠ ‫א‬
‫א‬‫א‬‫א‬ ‫א‬‫א‬ ‫א‬
 E‫א‬‫א‬F
 W‫א‬‫א‬ .١
O O
Cl
(2 CH 3CH 2C H (1


O O
C H
(4 (CH 3)2CHCCH(CH 3)2 (3

 O
CH 3CH 2CH 2 CCH 3 (5



 W‫א‬‫א‬‫א‬‫ א‬.٢

 Acetophenone (2 Benzaldehyde (1
Benzylphenyl ketone (4 Benzophenone (3
3-Pentanone (6  Butanal (5
 W‫א‬‫א‬ .٣

O O
? (1
C Cl + C
CH 3 CH 2 CH 2 C H
1) NaBH 4
2) H3O
+ ? (2
O
1) NaBH 4
+
? (3
2) H3O
CH 3 C CH 3
NH 2 OH
? (4
O
CH 3 C H
Oxidation.
? (5
O
CH 3 CH 2 C H
H 2 / Pt
? (6
- ١٠٠ -
 ‫א‬‫א‬ ١٤٠ ‫א‬
‫א‬‫א‬‫א‬ ‫א‬‫א‬ ‫א‬
E‫א‬‫א‬F
 WE1F‫א‬‫א‬
. 2-Chlorocyclohexanone (2  . Propanol (1
  . Methyl propyl ketone (3
 WE2F‫א‬‫א‬‫א‬
O CHO
(1
CH3 CH2 CH2 C-H (4
 
 O
CH3 CH2 CH2 C-CH3 (6

 WE3F‫א‬‫א‬‫א‬
N-OH
(4 
CH3 CH2 CH2 CH2 OH (2
CH3 -C- CH3

 OH
CH3 CH2 C CH3 (6


- ١٠١ -
 ‫א‬‫א‬‫א‬
‫א‬‫א‬‫א‬‫א‬
‫ א‬‫א‬
‫א‬
 ‫א‬‫א‬
 ‫א‬‫א‬
٨
 ‫א‬‫א‬ ١٤٠ ‫א‬
‫א‬‫א‬
‫א‬‫א‬ ‫א‬
 W‫א‬‫א‬
‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬ 
 K‫א‬‫א‬‫א‬‫א‬‫א‬

 W‫א‬‫א‬
 W‫א‬‫א‬‫א‬
 K‫א‬‫א‬ .١
 K‫א‬‫א‬‫א‬‫א‬ .٢

 W‫א‬‫א‬‫א‬
 K٪80‫א‬‫א‬‫א‬

 W‫א‬‫א‬
 K

 W‫א‬‫א‬
 KOverhead Projector  .١
 K .٢
 W‫א‬‫א‬
 K‫א‬‫א‬‫א‬‫א‬


- ١٠٢ -
 ‫א‬‫א‬ ١٤٠ ‫א‬
‫א‬‫א‬
‫א‬‫א‬ ‫א‬
 W8J 1
EJ COOH) ‫א‬‫א‬‫א‬
KE-OHF ‫א‬EC=OF‫א‬‫א‬K 
، ‫א‬
 ‫א‬‫א‬
 K‫א‬‫א‬
 W‫א‬‫א‬8J 2
 W‫א‬‫א‬J ‫א‬
‫א‬‫א‬‫א‬‫א‬
 ‫א‬‫א‬‫א‬
 KE8J 1FKW‫א‬‫א‬‫א‬‫א‬K
 WE‫א‬‫א‬‫א‬E8J 1FF
 ‫א‬  ‫א‬  ‫א‬‫א‬
‫א‬،Formic  Formic acid
HCOOH
 K‫א‬  ‫א‬
Acetum
 Acetic acid
‫א‬،‫א‬‫א‬
 CH3COOH 
‫א‬‫א‬
 ‫א‬
 K‫א‬
،Butyrum Butyric acid
CH3(CH2)2COOH
K‫א‬‫א‬‫א‬  K‫א‬

β،α‫א‬‫א‬،‫א‬‫א‬
‫א‬‫א‬α‫א‬‫א‬‫א‬‫א‬KKKγ،
 K‫א‬‫א‬‫א‬‫א‬‫א‬


- ١٠٣ -
 ‫א‬‫א‬ ١٤٠ ‫א‬
‫א‬‫א‬
‫א‬‫א‬ ‫א‬
‫א‬‫א‬ O
α γ β α
C C C C C C OH
‫א‬‫א‬ 5 4 3 2 1
 W
CH3 CH3
CH3 CH CH COOH
 2,3-Dimethylbutanoic acid 
 α،β -Dimethylbutyric acid 
 WIUPAC ‫א‬‫א‬W 

‫א‬‫א‬‫א‬e‫א‬oic acid ‫א‬
‫א‬‫א‬‫א‬K‫א‬‫א‬‫א‬
،‫א‬‫א‬‫א‬‫א‬
 W‫א‬‫א‬‫א‬‫א‬‫א‬
O Br
CH3 CH COOH
CH3 C OH
2-Bromopropanoic acid
Ethanoic acid
(Acetic acid)
COOH
CH3
CH3 C CHCOOH
Cyclohexane
3-Methyl-2-butenoic acid Carboxylic acid
- ١٠٤ -
 ‫א‬‫א‬ ١٤٠ ‫א‬
‫א‬‫א‬
‫א‬‫א‬ ‫א‬
 WW
 W‫א‬‫א‬‫א‬‫א‬ ‫א‬‫ א‬.١

COOH OH CH3
COOH
 Benzoic acid  Salicylic acid

COOH
 P-Toluic acid
 K
‫א‬ ‫א‬ .٢
 W
COOH
COOH COOH
COOH
CH2
COOH (CH2)4 COOH
CH2
CH2
COOH COOH
COOH
COOH
Oxalic acid Malonic acid Succinic acid Adipic acid Phthalic acid
‫א‬،Fatty acids‫א‬‫א‬ .٣
‫א‬، 2612‫א‬‫א‬‫א‬
‫א‬‫א‬ ،‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬
‫א‬
CH 3 (CH 2)14 COOH CH3 (CH 2)16 COOH
 W
Palmitic acid Stearic acid
 
- ١٠٥ -
 ‫א‬‫א‬ ١٤٠ ‫א‬
‫א‬‫א‬
‫א‬‫א‬ ‫א‬
 W‫א‬‫א‬‫א‬‫א‬8J 3
،‫א‬‫א‬‫א‬
‫א‬‫א‬،
 ‫א‬‫א‬‫א‬‫א‬‫א‬
‫א‬‫א‬‫א‬‫א‬‫א‬
 ‫א‬‫א‬‫א‬‫א‬،‫א‬
 W‫א‬‫א‬،‫א‬
KO100،L46Z‫א‬‫א‬ HCOOH Formic acid
 KO78،L46Z‫א‬‫א‬ C2H5OH Ethanol
‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬
‫א‬‫א‬‫א‬‫א‬،‫א‬
 ‫א‬‫א‬‫א‬
‫א‬‫א‬‫א‬‫א‬،‫א‬‫א‬‫א‬‫א‬،‫א‬
 K‫א‬
_ +
O H O
R C C R
+ _
 O H O
 E‫א‬‫א‬‫א‬F
 W‫א‬‫א‬8J 4
‫א‬‫א‬‫א‬‫א‬‫א‬
 K‫א‬‫א‬
_
H2O +
HCl H3O + Cl

‫א‬،‫א‬‫א‬‫א‬‫א‬‫א‬
 K‫א‬‫א‬
_ +

RCOOH + H2 O RCOO + H3 O
- ١٠٦ -
 ‫א‬‫א‬ ١٤٠ ‫א‬
‫א‬‫א‬
‫א‬‫א‬ ‫א‬
‫א‬‫א‬‫א‬‫א‬‫א‬
‫א‬‫א‬K‫א‬‫א‬‫א‬
 W‫א‬‫א‬‫א‬‫א‬
_
O O O
_
R C R C R C
_
O O O

 W‫א‬‫א‬‫א‬‫א‬‫א‬
 WElectron-withdrawing group‫א‬‫ א‬.١

‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬
‫א‬‫א‬‫א‬‫א‬K‫א‬‫א‬
 W‫א‬
 ....., -COOH , -SO3H , -CN , -NO2 , Br , Cl ,F
Benzoic acid p-Nitro Benzoic acid‫א‬
 KPara‫א‬‫ א‬-NO2
  :Electron-donating group‫א‬‫ א‬.٢

،‫א‬‫א‬‫א‬‫א‬‫א‬
،‫א‬‫א‬‫א‬
W
-OH , -NH2 , -OCH3 , -CH3
 ‫א‬‫א‬‫א‬‫א‬
 K‫א‬‫א‬‫א‬‫א‬J CH3‫א‬
‫א‬‫א‬‫א‬‫א‬‫א‬

 ‫א‬‫א‬‫א‬EInductetive effectF
‫א‬EpKaF‫א‬‫א‬‫א‬
 WEChlorobutyricF
- ١٠٧ -
 ‫א‬‫א‬ ١٤٠ ‫א‬
‫א‬‫א‬
‫א‬‫א‬ ‫א‬
Cl Cl Cl
CH3CH2CHCOOH CH3CHCH 2COOH CH2CH2CH2COOH

CH 3CH 2CH 2COOH
PKa = 4.82 PKa = 2.85 PKa = 4.05 PKa = 4.52
Z1 W 92 W 6 W 2
 ‫א‬

‫א‬Ka‫א‬‫א‬‫א‬
 W‫א‬‫א‬‫א‬ pKa
_ + 
[ RCOO ] [ H ]
Ka = [ RCOOH ]
_ log Ka = pKa
 K‫א‬pKaKa‫א‬
‫ﺗﺰداد اﻟﺤﻤﻮﺿﺔ‬ Ka ‫زﻳﺎدة‬
‫ﺗﻘﻞ اﻟﺤﻤﻮﺿﺔ‬ pKa ‫زﻳﺎدة‬

 W‫א‬‫א‬‫א‬‫א‬
 ‫א‬  pKa  Ka  ‫א‬
 Ð Ð  3.74  Ð 1.77*10-4 HCOOH
 Ð Ð 4.47  Ð 1.76*10-5 CH3COOH
 Ð Ð 4.85  Ð 1.43*10-5 CH3CH2COOH
 W‫א‬‫א‬8J 5
‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬
 W‫א‬‫א‬‫א‬،‫א‬‫א‬
- ١٠٨ -
 ‫א‬‫א‬ ١٤٠ ‫א‬
‫א‬‫א‬
‫א‬‫א‬ ‫א‬
 W‫א‬‫א‬‫א‬‫א‬ .١
O
H2Cr 2O7 +3
RCH 2 OH ( ‫) أﺧﻀﺮ اﻟﻠ ﻮن‬

OR R C H RCOOH + Cr
 W‫א‬ .٢
‫א‬‫א‬.(Ar)R-CN‫א‬‫א‬
 K‫א‬‫א‬‫א‬
_
CN  
 R-X RCN
 K‫א‬‫א‬‫א‬
+
H3O , +
RCN RCOOH + NH 4

 W‫א‬ .٣

R
KMnO4 ,
COOH
C2H5
KMnO4 ,
 Ethyl benzene Benzoic acid





- ١٠٩ -
 ‫א‬‫א‬ ١٤٠ ‫א‬
‫א‬‫א‬
‫א‬‫א‬ ‫א‬
 W‫א‬‫א‬ 8J 6
‫א‬
  K  ‫א‬‫א‬‫א‬
 K‫א‬‫א‬
 W‫א‬‫א‬‫א‬‫א‬‫ א‬.١
_
+
CH3COOH + NaOH CH3COO Na + H 2O
Acetic acid Sodium acetate

_ +
Ph COOH + NaOH Ph COO Na + H 2O
 Benzoic acid Sodium benzoate

،‫א‬ ‫א‬‫א‬‫א‬
 W‫א‬‫א‬
_ +
(Ar) R COOH + NaHCO 3 (Ar) R COO Na + H 2O + CO2

 K‫א‬،‫א‬‫א‬‫א‬
 W،‫א‬‫א‬ .٢
RCON
‫א‬‫א‬RCOOR‫א‬‫א‬RCOCl‫א‬‫א‬
O 
 K‫א‬
R-C-O-C-R
 W‫א‬‫א‬8- 7
E-OHF‫א‬‫א‬‫א‬‫א‬
‫א‬–NH2Cl-RCOO-J OR‫א‬
‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬
‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬
 W‫א‬‫א‬‫א‬‫א‬‫א‬
- ١١٠ -
 ‫א‬‫א‬ ١٤٠ ‫א‬
‫א‬‫א‬
‫א‬‫א‬ ‫א‬
 ‫א‬  ‫א‬‫א‬
O O
‫א‬
 CH3 C Cl Acetyl chloride
 R C X
O O
 
 CH3 C OC2H5 Ethyl acetate  R C OR
O
O
C NH2 ‫א‬
NH2
Benzamide  R C

O O O O
‫א‬
CH3 C O C CH3 Acetanhydride R C O C R
O O _
_
+  ‫א‬ +
 CH3 C O Na Sodium acetate  R C O M
 ‫א‬‫א‬7J 8J 1
 :Acid halides ‫א‬‫א‬W

،-yl halide‫א‬‫א‬‫א‬ - ic acid‫א‬
 W‫א‬‫א‬
O O
CH3 C OH CH3 C Cl
Acetic acid Acetyl chloride

 :Esters ‫א‬‫א‬W
‫א‬ ‫א‬‫א‬،-ate‫א‬‫א‬‫א‬ -ic acid‫א‬
 WKE‫א‬‫א‬F‫א‬‫א‬‫א‬‫א‬
- ١١١ -
 ‫א‬‫א‬ ١٤٠ ‫א‬
‫א‬‫א‬
‫א‬‫א‬ ‫א‬
O O
CH3 C OH CH3 C OC2H5
 Acetic acid Ethyl acetate

 WAmides‫א‬‫א‬W
 WKamide‫א‬‫א‬‫א‬J oicAcid‫א‬
O O
CH3 CH2 C OH CH3 CH2 C NH2
Propanoic acid Propanamide

 WAcid anhydrides‫א‬‫א‬W‫א‬
 .anhydrideacid‫א‬
O O O
C O OH C O C
Benzoic acid Benzoic anhydride


 :Acid salts‫א‬W
‫א‬‫א‬ ‫א‬‫א‬ ،‫א‬‫א‬‫א‬
 K‫א‬‫א‬
O O _ +
CH3 C OH CH3 C O NH 4
Acetic acid Ammonium acetate




- ١١٢ -
 ‫א‬‫א‬ ١٤٠ ‫א‬
‫א‬‫א‬
‫א‬‫א‬ ‫א‬
 W‫א‬‫א‬‫א‬‫א‬‫א‬7J 8J 2
‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬
‫א‬‫א‬،‫א‬‫א‬‫א‬ 
K‫א‬،‫א‬‫א‬‫א‬‫א‬‫א‬
‫א‬‫א‬‫א‬E‫א‬‫א‬F‫א‬‫א‬
 K‫א‬‫א‬‫א‬‫א‬‫א‬
‫א‬، ‫א‬‫א‬‫א‬
 K‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬
_ O
O O
.. + C
R-C-NH 2 R-C = NH 2 , .. +
R NH2

 ‫א‬‫א‬  ‫א‬‫א‬
‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬ 
 K‫א‬
- ١١٣ -
 ‫א‬‫א‬ ١٤٠ ‫א‬
‫א‬‫א‬
‫א‬‫א‬ ‫א‬
 W‫א‬‫א‬7J 8J 3
 K‫א‬
O
R C Cl
SOCl 2
in Benzene
O O O O
ROH
R C O C R R C OH R C OR
+
SH 2SO 4 H
Acid anhydride Acid Ester
NH 3 NaOH
O O _ +
R C NH 2 R C O Na
Acid salt
Amide











- ١١٤ -
 ‫א‬‫א‬ ١٤٠ ‫א‬
‫א‬‫א‬
‫א‬‫א‬ ‫א‬
 E‫א‬‫א‬F
 W‫א‬‫א‬ K١
O CO 2H
2) OH
1) CH 3 CH CH C OH
OH NH 2
NH 2
O O
_ +
CH3 CH2 CH 2 C O NH 4 4) CH 3 CH 2 C OCH 3
3)
O O O
CH 3
5) C O C CH 3 6) H C N
CH 3
O O
7) CH 3 CH 2 C Cl
8) CH3 CH 2 CH 2 C NH 2
 W‫א‬‫א‬‫א‬‫א‬‫ א‬K٢
a) 2,3-dibromopentanoic acid.
b) Methyl benzoate.
c) Methyl formamide.
d) m-nitrobenzoyl chloride.
e) Potassium formate.
f) N,N-diethylpropanamide.
g) Benzoic formic anhydride.
h) Ethyl 2-aminopropanoate.
 ‫؟‬‫א‬‫א‬‫א‬ K٣
 K‫א‬‫א‬ K 
 K‫א‬‫א‬ K
 K‫א‬‫א‬ K
 K‫א‬‫א‬ K
 K‫א‬‫א‬ K 
- ١١٥ -
 ‫א‬‫א‬ ١٤٠ ‫א‬
‫א‬‫א‬
‫א‬‫א‬ ‫א‬
 W‫א‬‫א‬ K٤
+
1) CN
H 2O / H
?
2) CH3 CH 2H5
KMnO 4
?
O
3) CH3CH2 C OH
SOCl 2
Benzene
?
O
4) CH3 C OH
H
+
?
O
5) 2CH3 C CH3 ?
H2SO4












- ١١٦ -
 ‫א‬‫א‬ ١٤٠ ‫א‬
‫א‬‫א‬
‫א‬‫א‬ ‫א‬
E‫א‬‫א‬F
 WE1F‫א‬‫א‬
2) 4-Amino-2-hydroxy benzoic acid.
4) Methyl propanoate.
5) Acetic benzoic anhydride.
7) Propanoyl chloride.
 WE2F‫א‬‫א‬
O
H-C-NHCH 3 (3 CH 3 -CH2-CH-CH-COOH (1
Br Br
O _ O O
+
H-C-O K (5
-C-O-C-H (7
 WE3F‫א‬‫א‬‫א‬

 ‫א‬‫א‬
 ‫א‬ K١
‫א‬‫א‬‫א‬‫א‬‫א‬
 K‫א‬
O O
+ _
H-C-OH H + H-C-O

 ‫א‬‫א‬‫א‬
  
+
 KE H ‫א‬،‫א‬F
O O _
+
CH3-C-OH H + CH3-C-O " ‫" اﻟﻘﺎﻋﺪة اﻟﻤﺮاﻓﻘﺔ‬
?‫א‬?E
  ‫א‬‫א‬CH3F  
 KEH+‫א‬F
- ١١٧ -
 ‫א‬‫א‬ ١٤٠ ‫א‬
‫א‬‫א‬
‫א‬‫א‬ ‫א‬
‫א‬،‫א‬‫א‬ K٢
‫א‬‫א‬،‫א‬‫א‬ ‫א‬
 K‫א‬‫א‬‫א‬
 WE4F‫א‬‫א‬‫א‬
O
HOOC COOH (2
CH3-C-O C 2H5 (4

- ١١٨ -
 ‫א‬‫א‬‫א‬
‫א‬‫א‬‫א‬‫א‬
‫ א‬‫א‬
‫א‬
‫א‬
‫א‬
٩
 ‫א‬‫א‬  ١٤٠  ‫א‬
 ‫א‬  ‫א‬‫א‬ ‫א‬
 W‫א‬‫א‬
‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬
 K‫א‬‫א‬‫א‬

 W‫א‬‫א‬
 W‫א‬‫א‬‫א‬
 K‫א‬ .١
 K‫א‬‫א‬‫א‬ .٢
 K‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬‫ א‬.٣

 W‫א‬‫א‬‫א‬
 K٪90‫א‬‫א‬‫א‬

 W‫א‬‫א‬
 K

 W‫א‬‫א‬
 KOverhead Projector  .١
K .٢

 W‫א‬‫א‬
K‫א‬‫א‬‫א‬‫א‬
- ١١٩ -
 ‫א‬‫א‬  ١٤٠  ‫א‬
 ‫א‬  ‫א‬‫א‬ ‫א‬
 W8-1
EF‫א‬ ‫א‬
‫א‬KEFEF‫א‬
‫א‬‫א‬KEF‫א‬‫א‬‫א‬‫א‬
 K‫א‬RR3N , R2NH , RNH2‫א‬‫א‬
‫א‬‫א‬ ‫א‬‫א‬‫א‬‫א‬
‫א‬‫א‬‫א‬ ‫א‬‫א‬‫א‬
‫א‬E‫א‬F‫א‬‫א‬‫א‬‫א‬‫א‬
 K‫א‬‫א‬‫א‬
 W‫א‬8-2
 W‫א‬8-2-1
 W‫א‬‫א‬‫א‬
 3O 2O  1O
  ‫א‬ ‫א‬
‫ א‬‫ א‬ K‫א‬
K‫א‬ K
(C2H5)3N (CH3)2NH CH3NH2  
Triethylamine Dimethylamine  Methylamine 

N NHCH3 NH2

Pyridine N-Methyl aniline  Aniline
- ١٢٠ -
 ‫א‬‫א‬  ١٤٠  ‫א‬
 ‫א‬  ‫א‬‫א‬ ‫א‬
 W‫א‬8-2-2
 W‫א‬‫א‬W
‫א‬amine‫א‬‫א‬‫א‬‫א‬
 W‫א‬‫א‬
CH3 CH3
CH3NH2
o CH3 NH CH3 N CH3
o
Methylamine (1) o
Dimethylamine (2)
Trimethylamine (3)
CH3 CH3
CH3CH2CHNH2 CH3CH2 N CH3
o o
sec-Butylamine (1) Ethydimethylamine (3)
 W‫א‬‫א‬‫א‬‫א‬
NH2
Cl NH(CH3)
Cl
NH2
NO2
Cl
O-Nitroaniline 2,4,6-Trichloroaniline N-Methylaniline
‫א‬‫א‬‫א‬‫א‬‫א‬
CH3 NH2
p-Toluidine
 KP- Toluidine‫א‬Toluidine‫א‬Aminotoluene
‫א‬،‫א‬‫א‬‫א‬‫א‬
 W‫א‬‫א‬
- ١٢١ -
 ‫א‬‫א‬  ١٤٠  ‫א‬
 ‫א‬  ‫א‬‫א‬ ‫א‬
N N
N N N
H H
H
Pyrrolidine Pyrrole Quinoline
Pipyridine Pyridine
 W‫א‬‫א‬W
‫א‬‫א‬‫א‬IUPAC‫א‬‫א‬‫א‬
‫א‬‫א‬Amino
‫א‬‫א‬،‫א‬‫א‬‫א‬
 W‫א‬
CH3 CH3 CH CH2 CH CH3
CH3 CH2 CH CH2 CH CH3 NH2
NH2
5-Methyl -3-aminohexane
2-Amino-4-phenylpentane
H2N CH2 CH2 CH2 COOH CH3 CH NH CH2 CH3
4-Aminobutanoic acid CH2CH2CH2CH3
2-(N-Ethyl amino)hexane
COOH
NH2
P-Aminobenzoic acid
 W‫א‬W
EAmmoniumFEAmineF
 ‫א‬‫א‬‫א‬‫א‬
‫א‬‫א‬‫א‬‫ א‬‫א‬(Anilinium)EAnilineF‫א‬
 W‫א‬
- ١٢٢ -
 ‫א‬‫א‬  ١٤٠  ‫א‬
 ‫א‬  ‫א‬‫א‬ ‫א‬
+ _
NH3 Br
CH3 _
+
CH3-N-CH 3 I
CH3
Tetramethylammonium Anilinium bromide

 W‫א‬‫א‬‫א‬8J 3
‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬ 
(C2H5)2NH, (CH3)3N, (CH3)2NH, WEF‫א‬‫א‬
J ٤F‫א‬‫א‬‫א‬‫א‬CH3NH2
‫א‬E11F E١١
 K‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬
،‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬
‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬
‫א‬‫א‬‫א‬‫א‬K
‫א‬‫א‬‫א‬‫א‬E ‫א‬‫א‬F‫א‬‫א‬
‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬
 KE8-1F‫א‬
 K‫א‬‫א‬‫א‬‫א‬‫א‬E8-1F‫א‬
‫א‬ 
‫א‬ ‫א‬‫א‬
 ‫א‬
  - 42 44 Propane CH3CH2CH2
   17 45 Ethylamine CH3CH2NH2
  7.5 45 Dimethylamine CH3NHCH 3
  78 46 Ethyl alcohol CH3CH2OH
  100.5 46 Formic acid
 HCOOH
  ‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬
 K‫א‬‫א‬‫א‬،‫א‬‫א‬K‫א‬‫א‬‫א‬،
- ١٢٣ -
 ‫א‬‫א‬  ١٤٠  ‫א‬
 ‫א‬  ‫א‬‫א‬ ‫א‬
 W‫א‬8- 4
،‫א‬‫א‬‫א‬‫א‬،‫א‬
‫א‬‫א‬
 ‫א‬ 
 K‫א‬‫א‬
_
+
 RNH 2 + HX
[ RNH 3 ] X
‫א‬‫א‬،‫א‬‫א‬‫א‬‫א‬
 ‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬
‫א‬‫א‬‫א‬‫א‬‫א‬،‫א‬
 W‫א‬‫א‬
. NH2 +
NH2
+
NH2
+
NH2
[ _
_
_
]
Resonance structures of aniline
 E‫א‬‫א‬‫א‬F
‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬
 K‫א‬–SO3H‫א‬–NO2‫א‬
 ‫א‬‫א‬‫א‬‫א‬
‫א‬‫א‬،‫א‬  ‫א‬–OCH3‫א‬
 ‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬
NH2 NH2 NH2
> >
OCH 3 NO2
‫ﺗﻘﻞ اﻟﻘﺎﻋﺪﻳﺔ ﺑﺎﺗﺠﺎﻩ اﻟﺴﻬﻢ‬

 
- ١٢٤ -
 ‫א‬‫א‬  ١٤٠  ‫א‬
 ‫א‬  ‫א‬‫א‬ ‫א‬
 ‫א‬‫א‬‫א‬‫א‬ ‫א‬

،‫א‬‫א‬‫א‬
 ‫א‬‫א‬‫א‬
،‫א‬‫א‬‫א‬‫א‬‫א‬، ‫א‬‫א‬‫א‬
‫א‬‫א‬‫א‬‫א‬
 ‫א‬‫א‬‫א‬‫א‬
‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬
 K‫א‬‫א‬Kb
+ _
R NH 2 + H2O R NH 3 + OH
Alkylammonium ion
 Amine
+ _
[ R _ NH3] [ OH ]
Kb =
 [ R _ NH2 ]
‫א‬ KK ‫א‬Kb
 ‫א‬ pKb  Kb‫א‬‫א‬
 W‫א‬‫א‬‫א‬pKb
NH2
 NH3  CH3NH2  (CH3)2 NH

_ 10 _5 _4 _4
K b = 4.2 * 10 K b = 1.8 * 10 K b= 4.4 * 10 K b= 5.1 * 10
pK b= 9.38 pK b= 4.74 pK b= 3.36 pK b= 3.29
  
  
 (CH3)3 N
pK b= 4.26   

_
10
  
K b = 5.5 * 10


- ١٢٥ -
 ‫א‬‫א‬  ١٤٠  ‫א‬
 ‫א‬  ‫א‬‫א‬ ‫א‬
 W‫א‬8-5
 W‫א‬
‫א‬‫א‬‫א‬ ‫א‬‫א‬‫א‬‫א‬‫א‬W 
 W‫א‬‫א‬
 W‫א‬‫א‬ J 
_
+ OH
H3N + R X R NH 3 X R NH 2 + H2O + X
o
Alkyl halide Primaryamine 1

 W‫א‬‫א‬‫א‬ J 

1) CH3Cl
CH 3CH 2NH 2 CH 3CH 2NH
2) OH
CH 3
‫أﻣﻴﻦ أوﻟﻲ‬ ‫أﻣﻴ ﻦ ﺛ ﺎﻧﻮي‬

o o
(1) (2)

 ‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬
 W‫א‬‫א‬‫א‬‫א‬–
‫א‬ ‫א‬K‫א‬‫א‬‫א‬‫א‬‫ א‬K
LIAIH4‫א‬ ‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬
 K‫א‬‫א‬‫א‬
H2 / Pt
CH3 NO2 CH3 NH2
Nitromethane Methylamine
+ _
Fe / HCl Na2CO3
NO2 NH3Cl NH2
 K‫א‬‫א‬‫א‬‫א‬‫א‬‫ א‬K
‫א‬‫א‬،‫א‬‫א‬‫א‬
‫א‬‫א‬‫א‬‫א‬ ‫א‬‫א‬LIAIH4‫א‬
 K‫א‬
- ١٢٦ -
 ‫א‬‫א‬  ١٤٠  ‫א‬
 ‫א‬  ‫א‬‫א‬ ‫א‬
H2 / Pd or
CH3CH2 C N CH3 CH2 CH2 NH2
LiAlH4 / Ether
H2 / Pd
C N CH2 NH2
‫א‬‫א‬Hofman degradation‫א‬W
NaOBr‫א‬‫א‬‫א‬‫א‬
 W‫א‬‫א‬E‫א‬‫א‬‫א‬F
O
4NaOH
CH 3(CH 2)4 C NH 2 + Br2 CH 3(CH 2)4 NH2 + By Products
H2O
‫א‬‫א‬‫א‬ ‫א‬،‫א‬‫א‬
 W
 K‫א‬‫א‬‫א‬ J ١
KNitroalkanes‫א‬‫א‬‫ א‬J ٢
‫א‬‫א‬‫א‬‫א‬ J ٣
‫א‬Nitrobenzene‫א‬‫א‬‫א‬Phenylamine
K‫א‬‫א‬‫א‬‫א‬‫א‬
- ١٢٧ -
 ‫א‬‫א‬  ١٤٠  ‫א‬
 ‫א‬  ‫א‬‫א‬ ‫א‬
 W‫א‬8- 6
 W‫א‬‫א‬
 W‫א‬HCl‫א‬‫א‬‫ א‬J ١
+ _
CH3 CH2 NH2 + HCl CH3 CH2 NH3 Cl
_
+
(CH3)3 N + HCl (CH3)3 NHCl
 WNitrous acid‫א‬‫ א‬J ٢
‫א‬–‫א‬‫א‬‫א‬‫א‬ J 
J F ‫א‬‫א‬NaNO2 ‫א‬
‫א‬‫א‬Diazonium salts‫א‬E٥O
‫א‬‫א‬،‫א‬‫א‬ ‫א‬K‫א‬
K‫א‬‫א‬‫א‬
O
0-5 C +
Ph NH2 + HNO2 Ph N2
Diazonium ion


‫א‬F‫א‬‫א‬‫א‬‫א‬‫א‬ J 

‫א‬‫א‬‫א‬‫א‬‫א‬ENaNO2HCl
‫א‬‫א‬
 ‫א‬‫א‬‫א‬،‫א‬
 KEFNitrosoamine
‫א‬‫א‬‫א‬‫א‬
 W‫א‬‫א‬
CH 3 (CH 2)4 CH 2 NH 2 HNO2
‫א‬ + N2
o
(1) amine
- ١٢٨ -
 ‫א‬‫א‬  ١٤٠  ‫א‬
 ‫א‬  ‫א‬‫א‬ ‫א‬
CH3(CH2) NH N=O
+ H2 O
o HNO2 CH3 CH2-N-CH 2 CH3 + H2O
2 amine N-Nitrosodiethylamine

HNO2
 (CH3 CH2)3 N No reactions.
 W‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬ J ٣
 ‫א‬J   ‫א‬J   ‫א‬J 
 W‫א‬‫א‬ K١
‫א‬‫א‬‫א‬ ‫א‬‫א‬
 K
NH2 NH2
Br2 / H2O
Br Br
Br
Aniline 2,4,6-Tribromoaniline
‫א‬‫א‬‫א‬
 K‫א‬‫א‬‫א‬‫א‬،
NH2 NHCOCH3 NHCOCH3 NH2
+
(CH3CO)2O Br2 H2O / H
Br
Br
Aniline Acetanilide p-Bromoacetanilide p-Bromoaniline
 W‫א‬‫א‬ K٢
‫א‬‫א‬‫א‬‫א‬
 
  ‫א‬‫א‬–N+H3‫א‬‫א‬
p- Nitroaniline 
 ‫א‬‫א‬‫א‬
 W‫א‬
- ١٢٩ -
 ‫א‬‫א‬  ١٤٠  ‫א‬
 ‫א‬  ‫א‬‫א‬ ‫א‬
NH2 NHCOCH 3 NHCOCH 3 NH2

O +
(CH3CO)2O H2SO4/15C H2O/H
H2 O
NO2 NO2
P-Nitroacetanilide P-Nitroaniline


 W‫א‬‫א‬ K٣
–‫א‬‫א‬‫א‬‫א‬ ‫א‬
 K
_
+ +
NH2 NH3HSO4 NH3
O
H2SO4 180-200 C
_
SO3
Aniline Anilinium hydrogen
Sulphanilic acid
sulphate
 W‫א‬‫א‬‫א‬٨J ٧
‫א‬،
 
،‫א‬‫א‬H2N-(CH2)6-H2N"1,6-hexamethylenediamine"
hexamethylenediamine
  
٢٧٠‫א‬C6H12N4W‫א‬‫א‬‫א‬،urotropin
،EformaldehydeF‫א‬‫א‬Ko
 o٩٥‫א‬E٪٢٧F‫א‬E٪٣٠F‫א‬
‫א‬‫א‬‫א‬،‫א‬‫א‬‫א‬
‫א‬‫א‬،octogen‫א‬hexogen‫א‬
C6H5-NH2 ‫א‬‫א‬
 ‫א‬‫א‬‫א‬‫א‬K‫א‬‫א‬
‫א‬‫א‬‫א‬‫א‬،‫א‬‫א‬‫א‬aniline
، ‫א‬‫א‬‫א‬‫א‬‫א‬،‫א‬‫א‬‫א‬‫א‬
- ١٣٠ -
 ‫א‬‫א‬  ١٤٠  ‫א‬
 ‫א‬  ‫א‬‫א‬ ‫א‬
‫א‬‫א‬ ‫א‬‫א‬،‫א‬‫א‬
‫א‬‫א‬،EhydroquinoneF،‫א‬
 KE‫א‬F‫א‬‫א‬‫א‬‫א‬
‫א‬‫א‬،
 ‫א‬‫א‬
 K،



- ١٣١ -
 ‫א‬‫א‬  ١٤٠  ‫א‬
 ‫א‬  ‫א‬‫א‬ ‫א‬
 E‫א‬‫א‬F
 W‫א‬‫א‬‫ א‬K١
1) CH3 CH2 N(CH3)2 2) CH3 CH2 CH CH3
NH2
+ _ 4) CH3 CH CH2 CH2CH2

3) CH3 CH2 N(CH3)3I
Br NH2
5) NH2 6) CH CH2 CH2

NH2 OH
Br
 W‫א‬‫א‬‫ א‬K٢
1) Cyclopentylamine . 2) B-phenylethylamine .
3) 1,6-Hexamethylendiamine . 4) Benzylamine .
5) N,N-Dimethylamine . 6)tetra-n-Butylammonium
iodide .
7) P-Aminobenzoic acid .
 K‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬ K٣
1) CH3 CH2 CH NH2 _
+
2) (CH3)3 NHNO3
CH3
4) (CH3CH2) C NH2
3) NH
_
+
5) N(CH3)2 Cl 6) NCH3
_
+
7) N(CH3)2 8) (CH3)2 CH N (CH3)3 Br
 K‫؟‬‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬ K٤
 W‫א‬‫א‬ K٥
O2 N NH 2
, CH 3O NH 2 , NH 2 (A

- ١٣٢ -
 ‫א‬‫א‬  ١٤٠  ‫א‬
 ‫א‬  ‫א‬‫א‬ ‫א‬
 NH3
, (CH3)2 NH , (CH3)3 N , CH3-C-NH 2 (B
 W‫א‬‫א‬ K٦
1) CH3Cl
a) (CH 3CH 2)2 NH
2) OH
?
Br Br
?
b)
NO2 NH2
H2 / Pt
c) CH3CH2CN ?
O
d) CH3CH2 C NH2 + Br2
4NaOH
?
H2O
+ _
e) CH3NH2 + ? CH3 NH3Cl
f) (CH 3CH2)2 N CH 3
HNO2
?
NH 2 NH 2
Br Br
g)
+ ?
Br
h) NH2 + CH3Cl ?



- ١٣٣ -
 ‫א‬‫א‬  ١٤٠  ‫א‬
 ‫א‬  ‫א‬‫א‬ ‫א‬
E‫א‬‫א‬F
 WE1F‫א‬‫א‬
1) Ethyl dimethyl amine . 4) 1-Amino-4-bromo pentane .
5) O- bromo aniline .
 WE٢F‫א‬‫א‬
CH 2NH 2
(4 NH 2 (1


 +
_
(CH 3CH 2CH 2CH2)4 N I (6

 WE٣F‫א‬‫א‬
 KE3  KE2
 KE6  KE4
 WE٥F‫א‬‫א‬
 P-methoxy aniline > Aniline > P-Nitro aniline .
 WE٦F‫א‬‫א‬
CH3CH 2CH2 NH2 (c (CH 3CH 2)2 N CH 3 (a
 K (f HCl (e


- ١٣٤ -
‫א‬‫א‬ ١٤٠ ‫א‬
‫א‬‫א‬ ‫א‬
 ‫א‬‫א‬
 W‫א‬‫א‬‫א‬
 ‫א‬‫א‬، K١
‫א‬W ‫א‬، ‫א‬ ‫א‬‫א‬K
 ١٩٨٩
‫א‬W‫א‬،‫א‬‫א‬K،‫א‬،‫ א‬K٢
 ١٩٩٠
 ١٩٩٦،‫א‬،‫א‬،‫א‬‫א‬K،‫ א‬K٣
١٩٩٨،‫א‬،‫א‬،‫א‬K‫א‬، K٤
،‫א‬‫א‬‫א‬K،‫א‬‫א‬،‫א‬،‫ א‬K٥
 ٢٠٠٠،‫א‬،‫א‬
 W‫א‬‫א‬‫א‬W
1.Fessenden, Ralph J.and Fessenden, Joan S. Organic Chemistry ,2nd ed, PWS, Boston
1982.
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‫א‬ ١٤٠ ‫א‬
‫א‬‫א‬ ‫א‬
 ‫א‬
‫א‬ 
 ١–‫א‬‫א‬
٢‫א‬ ١J ١
 ٣‫א‬‫א‬ ١J ٢
 ٥‫א‬‫א‬‫א‬ ١J ٣
 ٨ ١J ٤
١٠‫א‬–‫א‬‫א‬
 ١١‫א‬  ٢J ١
 ١١‫א‬  ٢J ٢
 ١٨‫א‬‫א‬‫א‬ ٢J ٢J ٢
 ١٨‫א‬‫א‬‫א‬ ٢J ٢J ٣
٢٢‫א‬ ٢J ٢J ٤
 ٢٣‫א‬  ٢J ٣
 ٢٣‫א‬ ٢J ٣J ١
 ٢٧‫א‬‫א‬‫א‬ ٢J ٣J ٢
 ٢٧‫א‬ ٢J ٣J ٣
 ٣١‫א‬ ٢J ٣J ٤
 ٣٢‫א‬  ٢J ٤
 ٣٢‫א‬ ٢J ٤J ١
 ٣٢‫א‬‫א‬‫א‬ ٢J ٤J ٢
 ٣٤‫א‬ ٢J ٤J ٣
 ٣٦‫א‬ ٢J ٤J ٤
٣٨‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬ ٢J ٤J ٥
 ٣٩  ٢J ٥
‫א‬ ١٤٠ ‫א‬
‫א‬‫א‬ ‫א‬
٤٢‫א‬‫א‬–‫א‬‫א‬
 ٤٣‫א‬  ٣J ١
 ٤٣‫א‬  ٣J ٢
 ٤٤‫א‬‫א‬  ٣J ٣
 ٤٥‫א‬‫א‬‫א‬  ٣J ٤
 ٤٦‫א‬  ٣J ٥
 ٤٩‫א‬‫א‬  ٣J ٦
 ٥٠‫א‬‫א‬  ٣J ٧
٥٦  ٣J ٨
٥٩‫א‬‫א‬‫א‬–‫א‬‫א‬‫א‬
 ٦٠‫א‬  ٤J ١
 ٦٠‫א‬‫א‬‫א‬  ٤J ٢
 ٦١‫א‬‫א‬‫א‬  ٤J ٣
 ٦٢‫א‬‫א‬‫א‬  ٤J ٤
 ٦٣‫א‬‫א‬‫א‬  ٤J ٥
 ٦٥‫א‬‫א‬‫א‬  ٤J ٦
 ٦٦  ٤J ٧
٦٩‫א‬‫א‬J ‫א‬‫א‬
 ٧٠‫א‬  ٥J ١
٧٠‫א‬  ٥J ٢
٧١‫א‬  ٥J ٣
٧٣‫א‬  ٥J ٤
٧٤‫א‬‫א‬‫א‬‫א‬  ٥J ٥
٧٥‫א‬‫א‬  ٥J ٦
٧٧‫א‬‫א‬  ٥J ٧
٨٠  ٥J ٨
‫א‬ ١٤٠ ‫א‬
‫א‬‫א‬ ‫א‬
٨٣‫א‬‫א‬–‫א‬‫א‬
 ٨٤‫א‬  ٦J ١
 ٨٤‫א‬‫א‬  ٦J ٢
 ٨٦‫א‬‫א‬‫א‬  ٦J ٣
 ٨٧‫א‬‫א‬  ٦J ٤
 ٨٨‫א‬‫א‬  ٦J ٥
 ٨٩  ٦J ٦
٩٢‫א‬‫א‬‫א‬–‫א‬‫א‬
 ٩٣‫א‬  ٧J ١
 ٩٣‫א‬‫א‬‫א‬  ٧J ٢
 ٩٦‫א‬‫א‬‫א‬  ٧J ٣
 ٩٧‫א‬‫א‬‫א‬  ٧J ٤
 ١٠٠  ٧J ٥
١٠٢‫א‬‫א‬–‫א‬‫א‬
 ١٠٣‫א‬  ٨J ١
 ١٠٣‫א‬‫א‬  ٨J ٢
 ١٠٦‫א‬‫א‬‫א‬‫א‬‫א‬  ٨J ٣
 ١٠٨‫א‬‫א‬  ٨J ٤
 ١١٠‫א‬‫א‬  ٨J ٥
 ١١٠‫א‬‫א‬  ٨J ٦
 ١١١‫א‬‫א‬ ٨J ٦J ١
 ١١٣‫א‬‫א‬‫א‬‫א‬‫א‬ ٨J ٦J ٢
 ١١٤‫א‬‫א‬ ٨J ٦J ٣
 ١١٥  ٨J ٧
‫א‬ ١٤٠ ‫א‬
‫א‬‫א‬ ‫א‬
١١٩‫א‬–‫א‬‫א‬
 ١٢٠‫א‬  ٩J ١
 ١٢٠‫א‬  ٩J ٢
 ١٢٣‫א‬‫א‬‫א‬  ٩J ٣
 ١٢٤‫א‬  ٩J ٤
 ١٢٦‫א‬  ٩J ٥
١٢٨‫א‬  ٩J ٦
 ١٣٠‫א‬‫א‬‫א‬  ٩J ٧
 ١٣٢  ٩J ٨

 ‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬
 ‫א‬E‫א‬F‫א‬‫א‬
GOTEVOT appreciates the financial support provided by BAE SYSTEMS

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 ‫א‬‫א‬‫א‬

 NH4OCN H2N C NH2

 WFunctional Group ‫א‬‫א‬١J ٢

H+ , Br+ , NO2+ , BF3 , AlCl3

 CH 3CH2OH + HBr CH3CH2Br +H2O

 CH2 CH2 + Br2 CH2BrCH 2Br

b) - CH3CH2I + NaSH CH3CH2SH + NaI

n  ‫א‬‫א‬ ‫א‬

 Pentane C5H12 W‫א‬‫א‬

 WAlkyl Group ER-F‫א‬

F: Fluoro NO2W Nitro

 ClW Chloro NH2W Amino

BrW Bromo CNW Cyano

CH4 + 2O2 CO2 (g) + 2H2O + ‫ﻃﺎﻗﺔ‬

H 2 /Pt ,Pd ‫ أو‬Ni _ _ _

 Alkyl halide Alkyl magnesium halide 

Mg(OH)Br + CH 3CH2CH2CH3 H2O

 2 CH 3 CH2 Cl + 2 Na CH3 CH2 CH2 CH3

 CH3 CH2 CH2 CH2 CH3 + CH3 CH2 Cu + LiBr

 2 CH 3 CH2 Li + Cul (CH 3 CH2)2 CuLi + Lil

 Ethylene CH 2=CH 2  Ethane CH3CH3

 Propylene CH3-CH =CH2 

–ene‫א‬‫א‬‫א‬‫א‬KKKKKKtetra،tri ،di ‫א‬

(‫آﺤﻮل )اﻳﺜﺎﻧﻮل‬ (‫اﻟﻜﻴﻦ )اﺛﻴﻠﻴﻦ‬

CH2 = CH2 + H2SO4 ‫ﻣﺮآﺰ‬ CH2 CH2

 (X = CI , Br) X X 

CaC2 + 2H2O C2H2 + Ca(OH) 2

Acetylene Methyl acetylene Ethyl acetylene 

Ethyne 1- Butyne 

CH4 + O2 2HC CH + 2CO + 10H2

CaCO3 CaO + CO2

CH3 C C CH3 + Cl2 CH3 C = C CH3 CH3 C C CH3

3-Ethyl-1-Methyl cyclohexane -‫ﺟـ‬ .٢

3-Methyl -1- butyne -‫هـ‬ .٣

 2- Bromo -3-Methyl -2- buteneJ 

CH3 CH=CH2 CH _ CH _ CH CHO

e) 4-bromo-2,3-dinitrotoluene f) m-chloro benzoic acid

CH3CH2OH +PBr3 CH3CH2Br + P (OH)3

 Nucleophilic substitution reactions‫א‬‫א‬‫א‬ K١

3◦ E 2◦ E  1◦ E

Isopropyl alcohol Tert-Butyl alcohol

Cyclopentyl alcohol Benzyl alcohol

 -ol  ‫א‬tetra,tri ,di‫א‬‫א‬‫א‬ K٤

 1,2-Ethanediol 1,2,3-Propantriol

 Ethylene glycol Glycerol or Glycerene

  water gas‫א‬‫א‬‫א‬‫א‬W‫א‬ K

 WNatural gas‫א‬‫א‬ K

Benzene sulfonic acid Sodium phenoxide Phenol

Benzene Chlorobezene Sodium phenoxide Phenol

Ethanol Diethyl ether

CH3 CH CH2 H2 C C CH2 OH

CH3 CH CH2CH3 CH3 C CH2CH3

‫א‬ ‫א‬ ‫א‬‫א‬ ‫א‬ ‫א‬

 o78  46 Ethanol CH3CH2OH

   o24J 46 Methylether CH3OCH3

  o42J 44 Propane CH3CH2CH3

Ethyl isopropyl ether

(1) + (2) CH3 C O CH2 (1

EArF،R R(Ar)-C-H W

CH3 C CH3 CH3 C CH( CH3)2

CH3 C H CH3 CH CH2 C H

CH3 C CH3 CH2 CH C CH3

 Ethyl phenyl ketone