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CHAPTER -14
Organic Chemistry
* Organic Chemistry is the chemistry of carbon compounds derived from living things both
animal and vegetable.
Hydro-carbons

↓ ↓
Saturated Hydrocarbon Unsaturated Hydrocarbon
↓ ↓
Alkane Alcohol Alkene Alkyne
↓ ↓ ↓ ↓
Single bond(-) CnH2n+2 O / Double bond (=) Triple bond( ≡)
CnH2n+2 CnH2n+1 OH CnH2n CnH2n-2
Substitution Addition Substitution /Addition
-C-C- -C=C- -C ≡C-

Bond Order

6
C = 2.4 -C- 1
H=1 H-
* C has bond order = 4 * H has bond order = 1
-O- (or) =O
* O has bond order = 2 * Halogen has bond order = 1

Name No: of carbon Name No: of carbon


Meth C1 Hex C6
Eth C2 Hept C7
Prop C3 Oct C8
But C4 Non C9
Pent C5 Dec C10

Properties of hydrocarbons
–The normal alkane from C1 to C4 are colourless gases, C5 to C17 are colourless liquids,
C18 and above are solids.
Molecular formula Structural formula
CH3–CH2–CH2–CH3 n-butane
C4H10 (butane)
CH3–CH–CH3 iso-butane
CH3
CH3–CH2–CH2–CH2–CH3 n-pentane
C5H12 (pentane) CH3–CH–CH2–CH3 iso-pentane
CH3
CH3
CH3–C –CH3 neo-pentane
CH3


































1. Molecular Formula
(a) Alkane (CnH2n+2 )
No: of Carbon Name Molecular Formula
1 methane CH4
2 ethane C2H6
3 propane C3H8
4 butane -------
5 pentane -------

(b) Alkene (CnH2n )


No: of Carbon Name Molecular Formula
1 - -
2 ethene C2H4
3 propene C3H6
4 butene C4H8

(c) Alkyne (CnH2n-2 )


No: of Carbon Name Molecular Formula
1 - -
2 ethyne C2H2
3 propyne C3H4
4 butyne C4H6
5 pentyne -------

Alkane/Alkene/Ankyne
HH
(a) H–C–C–H → CH2= CH2
HH ethene (ethylene)
ethane
HH H
(b) H–C–C–C–H → CH3– CH= CH2 H
HH H propene (propylene)
propane (methyl ethylene)
HH H H
(c) H–C–C–C–C–H → CH3– CH2– CH = CH2 H
HH H H 1-butene (1-butylene)
butane (ethyl ethylene)
HH H H
(d) H–C–C–C–C–H → CH3– CH = CH – CH3 H
HH H H 2-butene (2-butylene)
butane (dimethyl ethylene)
HH H HH CH3
(e) H–C–C–C–C-C–H → CH3 - C - CH3 Trivial neo
HH H HH CH3 CH3
neo pentane neo
(2,2-dimethyl propane)


































(f) H–C=C–H → H – C ≡C – H
H H ethyne
ethene (acetylene)
H H H
(g) H–C–C=C–H → CH3– C ≡ CH H
H propyne
propene (methyl acetylene)
H H H H
(h) H – C – C – C = C – H → CH3– CH2 – C ≡ CH H
H H 1-butyne
butene (ethyl acetylene)
H H H H
(i) H – C – C = C – C – H → CH3 – C ≡ C – CH3 H
H H 2-butyne
butene (dimethyl acetylene)
H H H H H
(j) H – C – C – C = C – C – H → CH3 – CH2 – C ≡ C – CH3 H
H H H 2-pentyne
pentene (ethyl methyl acetylene)

1. Structural Formula

(a) Alkane (CnH2n+2 )


No: of Carbon Name Structural Formula
1 methane CH4
2 ethane CH3- CH3
3 propane CH3-CH2- CH3
4 butane -------
5 pentane -------

(b) Alkene (CnH2n )


No: of Carbon Name Structural Formula
1 - -
2 ethene CH2= CH2
3 propene CH3-CH= CH2
4 1-butene CH3-CH2-CH= CH2
5 1-pentene -------

(c) Alkyne (CnH2n-2 )


No: of Carbon Name Structural Formula
1 - -
2 ethyne CH ≡CH
3 propyne CH3-C ≡CH
4 1-butyne CH3-CH2-C ≡CH
5 1-pentyne -------


































Graphical Formula
(a) Alkane ( CnH2n+2)
No: of Carbon Name Grphical Formula
H
1 methane H–C–H
H
H H
2 ethane H–C–C–H
H H
H H H
3 propane H–C–C–C–H
H H H
4 butane -----
5 pentane -----
(b) Alkene ( CnH2n)
No: of Carbon Name Grphical Formula
1 - -
H H
2 ethene C=C
H H
H H H
3 propene H–C–C=C
H H
H H H H
4 1-butene H–C–C–C=C
H H H
5 pentene -----
(c) Alkyne (CnH2n-2 )
No: of Carbon Name Graphical Formula
1 - -
H H
2 ethyne C ≡C
H H
3 propyne H - C - C ≡C
H
H H H
4 1-butyne H - C - C - C ≡C
H H

5 1-pentyne -------

Exercise

1.Write down the molecular formula of the following compounds.


(a) methane (b) propane (c) ethene (d) hexene
(e) butene (f) nonane (g) pentyne (h) heptane
(i) ethyne (j) heptene (k) octane (l) octyne


































2.Write down the structural formula of the following compounds.
(a) ethene (b) 1-butene (c) 1-octene (d) 1-heptyne
(e) 1-nonyne (f) hexane (g) propane (h) 1-pentene
(i) 1-butyne (j) decane (k) ethane (l) 1-hexyne

3.Write down the graphical formula of the following compounds.


(a) ethyne (b) 1-decyne (c) propyne (d) 1-decene
(e) hexane (f) 1-heptyne (g) 1-nonene (h) 1-octyne
(i) propane (j) 1-hexene (k)1-pentene (l) 1-butyne

4.Write down the name of the following compounds.


(a) C3H6 (b) C3H4 (c) C3H8 (d) C4H10
(e) C4H8 (f) C4H6 (g) C6H14 (h) C6H10
(i) C6H12 (j) C8H18 (k) C8H16 (l) C8H14

* Alkyl Radical (R–)

* CnH2n+2 (H ) CnH2n+1
Alkane → Alkyl

* CH4 (H ) CH3– (eg. CH3Cl methyl chloride)


Methane → methyl

* CH3- CH3 (H ) CH3- CH2– (eg. CH3CH2I ethyl iodide)


Ethane → ethyl

* CH3- CH2- CH3 (H ) CH3- CH2- CH2– (eg. CH3CH2CH2Br n-propyl bromide)
Propane → n-propyl
(H )
→ CH3- CH- CH3 (or) CH3- CH-
iso -propyl CH3
(eg. CH3– CHBr – CH3 iso-propyl bromide)

* R (Alkyl) (CnH2n+1)

methyl CH3–
ethyl CH3- CH2– normal
n -propyl CH3- CH2- CH2– iso
iso -propyl CH3- CH- CH3
Exercise
1.Write down the formula of the following compounds.
(a) alkyl iodide (b)ethyl chloride (c) methyl bromide (d) n-propyl halide
(e) iso-propyl chloride(f) methyl halide (g) iso-propyl halide (h) n-propyl iodide
(i) iso-propyl iodide (j) n-propy bromide (k) iso-propyl bromide (l) n-propyl bromide
(m) ethyl bromide (n) methyl iodide


































1.Write down the name of the following compounds.

(a) CH3Cl (b) CH3-CHBr-CH3 (c) RX (d) CH3- CH2X


(e) CH3-CH2-CH2I (f) CH3-CH2Br (g) CH3-CHX-CH3 (h) CH3-CH2-CH2Cl
(i) CH3-CHI-CH3 (j) CH3- CH2Cl (k) CH3I (l) CH3-CHCl-CH3
(m) CH3-CH2-CH2X (n)CH3X (o) CH3-CH2-CH2Br

IUPAC (OR) Geneva system

*IUPAC = International Union of Pure and Applied Chemistry

* Alkane

Formula ⇒ IUPAC name

IUPAC

Example (1) Give the IUPAC name of the following compounds.

(a) CH3-CH2-CH2-CH2-CH-CH2-CH3 Ans; 3- methyl heptane


CH3
CH3
(b) CH3-CH2-CH2- CH - CH2 -C- CH2-CH3 Ans; 5-ethyl 3,3-dimethyl octane
CH2 CH3
CH3

IUPAC name ⇒ Formula

C bond
H

Example (2) Draw the structural formula of the following compounds.

(a) 4,4,5-trimethyl octane


CH3
Ans; CH3- CH2- CH2- CH - C - CH2- CH2- CH3
CH3 CH3

(b) 4-ethyl 2-methyl hexane

Ans; CH3-CH2-CH-CH2-CH-CH3
CH2 CH3
CH3


































Naming of Alcohols (IUPAC system and Trivial system)

Alkane Alcohol IUPAC system Trivial system


*CH4 CH3-OH methanol methyl alcohol
(methane) (or) wood spirit

*CH3-CH3 CH3-CH2OH ethanol ethyl alcohol (or)


(ethane) rectified spirit

*CH3-CH2-CH3 CH3-CH2-CH2OH propan-1-ol n-propyl alcohol


(propane) CH3-CHOH-CH3 propan-2-ol iso-propyl alcohol

*CH3-CH2-CH2-CH3 CH3-CH2-CH2-CH2OH butan-1-ol n-butyl alcohol


(n-butane) CH3-CH2-CHOH-CH3 butan-2-ol sec-butyl alcohol

*CH3-CH-CH3 CH3-CH-CH2OH 2-methyl iso-butyl alcohol


CH3 CH3 propan-1-ol
(iso-butane or (or) iso-butanol
2-methyl propane)

CH3
*CH3-CH-CH3 CH3-C -OH 2-methyl tertiary butyl alcohol
CH3 CH3 propan-2-ol(or)
(OR) OH tertiary butanol
CH3-C-CH3
CH3

*Diol (dialcohol)

Alkane Dialcohol IUPAC system Other name


*CH4 Do not exist - -
(methane)

*CH3-CH3 CH3OH-CH2OH ethan-1,2-diol ethene glycol (or)


1,2-dihydroxy ethane

*CH3-CH2-CH3 CH3-CHOH-CH2OH propan-1,2-diol propene glycol (or)


1,2-dihydroxy propane

*CH3-CH2-CH2-CH3 CH3-CH2-CHOH-CH2OH butan-1,2-diol 1,2-dihydroxy butane


CH3-CHOH-CHOH-CH3 butan-2,3-diol 2,3-dihydroxy butane

OH
*CH3-CH-CH3 CH3-C -CH2OH 2-methyl 1,2-dihydroxy
CH3 CH3 propan-1,2-diol 2-methyl propane


































*Alkene / Alkyne / Alcohol

Formula ⇒ IUPAC name

[ (=) / ( ≡) / ( OH ) ]
[ (=) / ( ≡) / ( OH ) ]
IUPAC

Example (1) Give the IUPAC name of the following compounds.

(a) C H- CH - CH = CH - CH3
3
(b) CH3- CH - CH - CH2- C ≡C - CH3
CH3 CH3 CH3
Ans; 4- methyl 2-pentene Ans; 5,6-dimethyl 2-heptyne
CH3 CH3
(c) CH3- CH2 - C - CHOH - CH2- CH3 (d) CH3- CH2 - C - CHOH - CHOH- CH3
CH3 CH3
Ans; 4,4-dimethyl hexan-3-ol Ans; 4,4-dimethyl hexan-2,3-diol

Example (2) Give the Structural formula of the following compounds.

(a) 5-methyl 1-hexene (b) 4-methyl 2-heptene


CH3 - CH - CH2 - CH2 - CH = CH2 CH3 - CH2 - CH2 - CH - CH = CH - CH3
CH3 CH3

(c) 3-methyl 1-butyne (d) 2-methyl propan-2-ol


CH3- CH - C ≡CH CH3- COH - CH3
CH3 CH3

Exercise
*Alkane (-)

1.Give the IUPAC name of the following compounds.


CH3
(a) CH3- CH - CH2- CH3 (b) CH3 - CH2 - CH - CH - C - CH3
CH3 CH2 CH3 CH3
CH3

CH3
(c) CH3- CH - CH - CH2- CH3 (d) CH3- CH - CH2- CH - CH - CH3
CH2 CH2 CH3 CH3
CH2 CH3
CH3


































(e) CH3- CH - CH2- CH2-CH2-CH3 (f) CH3- CH2- CH - CH - CH3
CH3 CH2 CH3
CH3

2. Draw the Structural formula of the following compounds.

(a) 3-methyl hexane (b) 2-methyl butane

(c) 3,4-dimethyl heptane (d) 4-ethyl 3-methyl octane

(e) 2-methyl pentane (f) 3,3,4-trimethyl octane

(g) 3-ethyl 2,2-dimethyl decane (h) 5-ethyl 3,4-methyl nonane

*Alkene (=)

1.Give the IUPAC name of the following compounds.


CH3
(a) CH3- CH- CH = CH - CH3 (b) CH3- CH2- CH2- CH - CH2- C - CH = CH - CH3
CH2 CH2 CH3
CH3 CH3

CH3
(c) CH3- CH = CH - CH - CH3 (d) CH3- CH2- C - CH - CH = CH2
CH3 CH3 CH3

CH3
(e) CH3- C = CH2 (f) CH2= CH - C - CH3
CH3 CH3

CH3
(g) CH3- CH = CH - CH - CH3 (h) CH3-CH2 - C - C = CH - CH3
CH2 CH3 CH2- CH3
CH3

2. Draw the Structural formula of the following compounds.

(a) 3-methyl 2-hexene (b) 3,3-dimethyl 1-octene

(c) 6-ethyl 3-methyl1-nonene (d) 2-methyl 1-propene

(e) 4-ethyl 2-heptene (f) 4-methyl 2-butene

(g) 7-methyl 3-decene (h) 3-ethyl 1-pentene




































* Alkyne ( ≡)

1.Give the IUPAC name of the following compounds.


C H
3
(a) CH3- C - C ≡C - CH3 (b) CH3- CH - CH2 - C ≡C - CH3
CH3 CH3

(c) CH3- C ≡C - CH - CH3 (d) CH3 - CH2 - CH - CH - CH - C ≡C - CH3


CH3 CH2 CH3 CH3
CH3

(e) CH3 - C ≡C - CH - CH3 (f) CH3- C ≡C - CH2 - CH3


CH2
CH3

CH3
(g) CH3- CH - C ≡C - CH2- CH3 (h) CH3- C ≡C - CH2 - CH2 - CH2 - CH - CH3
CH2- CH3

2. Draw the Structural formula of the following compounds.

(a) 4-methyl 2-pentyne (b) 2-butyne

(c) 4,5-dimethyl 2-hexyne (d) 3,3-dimethyl 4-ethyl 1-noyne

(e) 4-methyl 1-hexyne (f) 6-ethyl 4,5,5-trimethyl 2-decyne

(g) 6-methyl 2-octyne (h) 3-methyl 1-butyne

*Alcohol (OH)

1.Give the IUPAC name of the following compounds.

(a) CH3- CH- CH2OH (b) CH3- CH2- CH - CHOH - CH2


CH2 - CH3 CH3 CH3

(c) CH3- CH - CH - CH2OH (d) CH3- CH - CH - CHOH -CH2 - CH2 - CH3


CH3 CH3 CH3 CH3

(e) CH3 -CHOH - CH3 (f) CH3 -CHOH -CH2 - CH3

(g) CH3- CH2 - CH - CH2 - CH2OH (h) CH3-CH2- CH2-CHOH - CHOH -CH2 - CH3
CH2
CH3


































(2) Draw the Structural formula of the following compounds.

(a) 4-methyl pentan-2-ol (b) 6,6-dimethyl heptan-1-ol

(c) propan-2-ol (d) 6,7,7-trimethyl nonan-4-ol

(e) 6-ethyl nonan-1,3-diol (f) butan-1-ol

(g) 4-methyl hexan-1-ol (h) 7-ethyl 4,5-dimethyl decan-2,3-diol

*Alkane (-)
- Alkane equation
(I) Preparation of Alkane
(II) Chemical properties of Alkane

(I) Preparation of Alkane

- RCOONa ⇒ sodium alkanoate ( sodium carboxylate)


- CH3COONa ⇒ sodium ethanoate ( sodium acetate)
- CH3-CH2COONa ⇒ sodium propanoate (sodium propionate)
- CH3-CH2-CH2-COONa ⇒ sodium butanoate
(1) Sodium alkanoate is heated with sodalime

alkane
CaO ane
CaO
(a) RCOONa + NaOH → RH + Na2CO3
Δ
sodium soda-lime alkane
alkanoate
CaO
(b) CH3COONa + NaOH → CH4 + Na2CO3
Δ
sodium soda-lime methane
ethanoate
CaO
(c) CH3-CH2COONa + NaOH → CH3-CH3 + Na2CO3
Δ
sodium soda-lime ethane
propanoate
CaO
(d) CH3-CH2-CH2-COONa + NaOH → CH3-CH2-CH3 + Na2CO3
Δ
sodium butanoate soda-lime propane


































(1) Reduction of RI with HI

(a) RI + HI → RH + I2
alkyl alkane
iodide
(b) CH3I + HI → CH4 + I2
methyl methane
iodide
(c) CH3-CH2I + HI → CH3-CH3 + I2
ethyl ethane
iodide
(d) CH3-CH2-CH2I + HI → CH3-CH2-CH3 + I2
n-propyl propane
iodide
(e) CH3-CHI-CH3 + HI → CH3-CH2-CH3 + I2
iso-propyl propane
iodide

(2) Reduction of RI with H2

Pt/Pd
H2 catalyst
Ni, 300� C

Pt / Pd
(a) RI + H2 RH + HI

alkyl iodide alkane
Pt / Pd
(b) CH3I + H2 CH4 + HI

methyl iodide methane
Pt / Pd
(c) CH3-CH2I + H2 CH3-CH3 + HI

ethyl iodide ethane
Pt / Pd
(d) CH3-CH2-CH2I + H2 CH3-CH2-CH3 + HI

n-propyl iodide propane
Pt / Pd
(e) CH3-CHI-CH3 + H2 CH3-CH2-CH3 + HI

iso-propyl iodide propane

(3) Reduction of alkene with H2


Ni,300� C
(=) + H2 → (-)
Pt / Pd
alkene alkane


































Ni,300� C
(a) CH2 = CH2 + H2 → CH3 - CH3
Pt / Pd
ethene ethane
Ni,300� C
(b) CH2 -CH= CH2 + H2 → CH3 - CH2- CH3
Pt / Pd
propene propane

(II) Chemical properties of alkane

(1) Combustion O2
Δ
(a) CH4 + 2O2 CO2 + 2H2O

methane
7 Δ
(b) CH3-CH3 + O2 2CO2 + 3H2O
2 →
ethane
Δ
(c) CH3-CH2-CH3 + 5O2 3CO2 + 4H2O

propane

(2) Substitution reaction of alkane(Chlorination) Cl

* methane + Chlo
H Cl HCl Chloroform CHCl3
diffused
CH4 + Cl2 → CH3Cl + HCl
sunlight
methane methyl chloride
diffused
CH3Cl + Cl2 → CH2Cl2 + HCl
sunlight
methyl chloride methylene chloride
diffused
CH2Cl2 + Cl2 → CHCl3 + HCl
sunlight
methylene chloride chloroform
diffused
CHCl3 + Cl2 → CCl4 + HCl
sunlight
chloroform carbon tetrachloride


































Alkane equation

(1) RCOONa + NaOH → ?


(2) CH3COONa + NaOH → ?
(3) CH3-CH2COONa + NaOH → ?
(4) CH3-CH2-CH2COONa+ NaOH → ?
(5) RI + HI → ?
(6) CH3I + HI → ?
(7) CH3-CH2I + HI → ?
(8) CH3-CH2-CH2I + HI → ?
(9) CH3-CHI-CH3 + HI → ?
(10) RI + H2 → ?
(11) CH3I + H2 → ?
(12) CH3-CH2I + H2 → ?
(13) CH3-CH2-CH2I + H2 → ?
(14) CH3-CHI-CH3 + H2 → ?
(15) CH2= CH2 + H2 → ?
(16) CH 3-CH = CH2 + H2 → ?
(17) CH 3- CH2 -CH= CH2 + H2 → ?
(18) CH4 + O2 → ?
(19) CH 3- CH3 + O2 → ?
(20) CH3-CH2-CH3 + O2 → ?
(21) CH4 + Cl2 → ?
(22) + Cl2 → ?
(23) + Cl2 → ?
(24) + Cl2 → ?
Exercise
(1) What happen when
(a) CH3COONa + NaOH → ?
(b) CH3-CH2COONa + NaOH → ?
(c) C3H7COONa + NaOH → ?
(d) R-CH2COONa + NaOH → ?
(e) CH3I + H2 → ?
(f) CH3-CH2I + HI → ?
(g) CH3-CH2-CH2I + HI → ?
(h) CH4 + Cl2 → ?
(j) CH4 + O2 → ?
(k) CH3-CH3 + O2 → ?

(2) What happen when


(a)R-CH2COONa is heated with sodalime?
(b) R-CH2-CH2COONa is heated with sodalime?
(c) Sodium ethanoate is heated with sodalime?
(d) Sodium propanoate is heated with sodalime?
(e) Heating sodium butanoate with sodalime?
(f) Methyl iodide is treated with hydrogen iodide?
(g) Ethyl iodide is treated with hydrogen iodide?
(h) Methane is mixed with chlorine is diffused sunlight?


































(3) Illustrate the following reactions
(a) Chlorination (b) Combustion of methane
(4) How would you prepare
(a) ethane from ethene (b) propane from propylene
(c) ethane from ethyl iodide (d) methane from sodium ethanoate
(e) ethane from sodium propanoate (f) methane from methyl iodide
(5) Answer the following equations.
(a) By heating a mixture of sodium propanoate and sodalime , a gas '' A '' is evolved .
What is gas '' A ''? Write down the equation.
(b) A gas '' X '' is obtained by heating a mixture of sodium ethanoate and sodalime.
What is gas '' X ''? Write down the equation.
(c) A gas '' X '' is obtained by heating a mixture of '' Y '' and sodalime . '' Y '' may be obtained
from the reaction between NaOH and acetic acid . Write down the balanced equation in
symbols for the first reaction only, and name the compounds ''X'' and ''Y''.
(d) Gas '' A '' can be formed by hydrogen of propene using a nickel catalyst at 300°C.
Write down the chemical equation and name the gas '' A ''.

Alkene (=)
- Alkene equation
(I) Preparation of Alkene
(II) Chemical properties of Alkene
(I) Preparation of Alkene
1. Dehydration of alcohol ( H2O

nol (alcohol)
''160'' ''ene''

Alumina ''350''
160° C , H 2SO 4 ( conc )
ROH → (=) + H2O
350° C , Al 2O 3

alcohol alkene
160° C , H 2SO 4 ( conc )
CH3-CH2OH → CH2 = CH2 + H2O
350° C , Al 2O 3

ethanol ethene
(ethyl alcohol)
160° C , H 2SO 4 ( conc )
CH3-CH2-CH2OH → CH3-CH= CH2 + H2O
350° C , Al 2O 3

porpanol propene
(n-propyl alcohol)
160° C , H 2SO 4 ( conc )
CH3-CHOH -CH3 → CH3-CH= CH2 + H2O
350° C , Al 2O 3

propanol propene
(iso-propyl alcohol)


































2. Dehydrohalogenation of alkyl halide
eth y l c h lo r i d e KOH ethanol ( Δ ) ethene KCl
ethanol
CH3-CH2Cl + KOH → CH2=CH2 + KCl + H2O
Δ

ethyl chloride ethene


ethanol
CH3-CH2-CH2Cl + KOH → CH3-CH=CH2 + KCl + H2O
Δ

n-propyl chloride propene


ethanol
CH3-CHCl -CH3 + KOH → CH3-CH=CH2 + KCl + H2O
Δ

iso-propyl chloride propene


(II) Chemical properties of Alkene
1. Combustion
Δ
CH2=CH2 (ethene) + 3O2 → 2CO2 + 2H2O
9 Δ
CH3-CH=CH2 (propene) + ( )O → 3CO2 + 3H2O
2 2
2. Addition reaction ( H2 , X2 , HX )
(a) Hydrogenation ( H2 )
Pt / Pd
CH2=CH2 + H2 → CH3-CH3
ethene ethane
Pt / Pd
CH3-CH =CH2 + H2 → CH3-CH2-CH3
propene propane
(b) Halogenation ( X2 )
CH2=CH2 + X2 → CH2 X-CH2X
ethene ethene dihalide
CH3-CH=CH2 + X2 → CH2X-CH2-CH2X
propene propene dihalide
*
(c) Hydrohalogenation ( HX-addendum )
CH2=CH2 + HX → CH3 -CH2X
ethene ethyl halide
( symmetrical alkene)
CH3-CH=CH2 + HX → CH3-CHX-CH3 + CH3-CH2-CH2X
propene iso-propyl halide n-propyl halide
( unsymmetrical alkene) (major product) (minor product)
CH2=CH2 + HCl → CH3 - CH2Cl
ethene ethyl chloride
( symmetrical alkene)
CH3-CH=CH2 + HCl → CH3-CHCl-CH3 + CH3-CH2-CH2Cl
propene iso-propyl chloride n-propyl chloride
( unsymmetrical alkene) (major product) (minor product)


































Markownikoff 's Rule
- When an unsymmetrical addendum (HX) adds on to an unsymmetrical alkene, two
products are possible; but that product where the negative part of the addendum adds
on to the carbon with the least number of hydrogen atom is the major product.

3. Formation of ozonide (Ozonolysis) (O3

* ethene Ozone (O3)


Zn dust propene
O
chloroform Zn
CH2=CH2 + O3 → CH2 CH2 + H2O → CH2O + CH2O + H2O2
CHCl 3 dust

O O
ethene ethene ozonide methanal methanal
O
chloroform Zn
CH3-CH=CH2 + O3 → CH3-CH CH2 + H2O → CH3-CHO + CH2O + H2O2
CHCl 3 dust

O O
propene propene ozonide ethanal methanal

4. Hydroxylation (OH
ethene KMnO4 ethene glycol
propene KMnO4 propene glycol
1 � � KMnO 4
CH2=CH2 + H2O + [O] → CH2OH-CH2OH
cold ( dil ) violet

ethene ethene glycol (colourless)


1 � � KMnO 4
CH3-CH=CH2 + H2O + [O] → CH3-CHOH -CH2OH
cold ( dil ) violet

propene propene glycol (colourless)

* n-butane and 1-butene


1-butene can decolourize the reddish brown colour of bromine solution in ethanol, but
n-butane does not.
ethanol
CH3-CH2CH=CH2 + Br2 → CH3-CH2CHBr-CH2Br
1-butene (reddish brown) 1,2-dibromobutane(colourless)
ethanol
CH3-CH2CH2CH3 + Br2 → (colour is not dicharged)
n-butane (reddish brown)


































* iso-butane and iso - butene
Iso-butene can decolourize the reddish brown colour of bromine solution in ethanol,
but iso-butane does not.
ethanol
CH3-C = CH2 + Br2 → CH3-CBr-CH2Br
CH3 CH3
iso-butene (reddish brown) 1,2-dibromo-2-methyl propane(colourless)
ethanol
CH3-CH - CH3 + Br2 → CH3-CBr-CH2Br
CH3 CH3
ethanol
iso-butane (reddish brown) → (No colour discharge)

5. Polymerization
( poly ethene >1000 atm
n poly
>1000 atm
n ( CH2=CH2 ) → ( CH2– CH2 ) n
Δ

ethene poly ethene


>1000 atm
n (CH3-CH=CH2) → ( CH2– CH2 ) n
Δ

CH3
propene poly propene

Exercise
(i) Complete the following reactions.
1. CH3-CH2OH → ?
2. CH3-CH2-CH2OH → ?
3. CH3-CHOH-CH3 → ?
4. CH3-CH2X + KOH → ?
5. CH3-CH2-CH2Cl + KOH → ?
6. CH3-CHBr-CH3 + KOH → ?
7. CH2=CH2 + O2 → ?
8. CH3-CH=CH2 + O2 → ?
9. CH2=CH2 + H2 → ?
10. CH2-CH=CH2 + H2 → ?
11. CH2=CH2 + Cl2 → ?
12. CH3-CH=CH2 + Cl2 → ?
13. CH2=CH2 + Br2 → ?
14. CH3-CH=CH2 + Br2 → ?
15. CH2=CH2 + HBr → ?
16. CH3-CH=CH2 + HCl → ?
17. CH2=CH2 + O3 → ?
18. CH3-CH=CH2 + O3 → ?
19. CH2=CH2 + H2O + [O] → ?
20. CH3-CH=CH2 + H2O + [O] → ?
21. R- CH=CH2 + H2O + [O] → ?
22. n (CH3-CH=CH2) → ?


































(ii) What happen when
1. ethanol is passed over alumina,Al2O3 heated at 350 � C ?
2. ethanol is heated with H2SO4(conc) at 160 � C ?
3. n-propyl alcohol is heated with concentrated sulphuric acid at 160 � C ?
4. passing propyl alcohol over alumina at 350 � C ?
5. ethyl chloride is heated with alcoholic solution of KOH?
6. n-propyl chloride is heated with alcoholic solution of potassium hydroxide?
7. iso-propyl chloride is heated with alcoholic solution of potassium hydroxide?
8. an alkyl halide is heated with alcoholic solution of potassium hydroxide?
9. propene is passed into bromine solution.
10.propene reacts with hydrogen halide?(or)symmerical alkene with unsymmerical addendum?
11. addition of hydrogen bromide to propene.
12. ethene is passid into 1% KMnO4?
13. propene is passed into cold dilute potassium permaganate solution?
14. ozonized oxygen is passed into ethene in chloride and product is decomposed by water?
15. ethene ozonide is decomposed with water?

(iii) Complete the following reaction.


1. Dehydration of n-propyl alcohol
2. Addition reaction (Hydrogenation of ethene with nickel catalyst)
3. Dehydrohalogenation of n-propyl chloride
4. Dehydrohalogenation of iso-propyl chloride
5. Ozonolysis (Formation of ozonide)
6. Ozonolysis of propene
7. Hydroxylation ( Formation of glycol)
8. Hydroxylation of propene
9. Hydrogenation of propene

(iv) How would you prepare?


1. ethene from ethanol
2. methanal from ethene
3. propene from iso-propyl chloride

(v) Answer the following questions?


1. A gas ''Y'' is obtained by heating a mixture of ethanol and concentrated sulphuric acid at
160 � C . What is gas ''Y''? Write down the chemical equation.
2. A gas ''G'' is obtained by passing the vapour of ethanol over alumina at 350 � C . What is gas
''G'' ? Write down the chemical equation.
3. A gas ''X'' is obtained by heating ethyl chloride with on alcoholic potassium hydroxide on a
water batch.What is gas ''X''? Write down the chemical equation.
4. A gas ''B'' is obtained by heating n-propyl bromide with on alcoholic potassium hydroxide
on a water batch.What is gas ''B''? Write down the chemical equation.
5. A gas ''B'' is obtained by passing the vapour of propanol and alumina at 350 � C . What is gas
''B'' ? Write down the chemical equation.
6. When compound X undergoes ozonolysis the final product is methanal. What is compound
X? Write down the relevant equation.


































Alkyne
Alkyne equation
(I) Preparation of Alkyne
(II) Chemical properties of Alkyne

(I) Preparation of Alkyne


CH2= CHX ⇒ vinyl halide CH3-CHX2 ⇒ ethylidene halide
CH2= CHCl ⇒ vinyl chloride CH3-CHCl2 ⇒ ethylidene chloride
CH2= CHBr ⇒ vinyl bromide CH3-CHBr2 ⇒ ethylidene bromide
CH2= CHI ⇒ vinyl iodide CH3-CHI2 ⇒ ethylidene iodide
CH3-CHOH ⇒ vinyl alcohol
1. Ethyne from coke
CaO + 3C electric furance CaC2 + CO
quick

lime
coke
→ calcium

carbide

CaC2 + 2H2O
→ CH ≡ CH

ethyne
+ Ca (OH)2

slaked lime
coke CaO electric furance
carbide H2 O ethyne
2. Dehydrohalgenation
ethene dibro KOH ethanol ( Δ ) ethyne KBr
ethylidene chlo KOH ethanol ( Δ ) ethyne KCl
(a) Dehydrohalgenation of ethene dibromide
ethanol
CH2Br - CH2Br + 2KOH → CH ≡ CH + 2KBr + 2H2O
Δ

ethene dibromide ethyne


(b) Dehydrohalgenation of ethylidene chloride
ethanol
CH3 - CHCl2 + 2KOH → CH ≡ CH + 2KCl + 2H2O
Δ

ethylidene chloride ethyne


(II) Chemical properties of Alkyne
1. Combustion
5 Δ
CH ≡ CH (ethyne) + O → 2CO2 + H2O
2 2
Δ
CH3 -C ≡ CH (propyne) + 4O2 → 3CO2 + 2H2O

2. Addition reaction (H2 , X2 , HX)


(a) Hydrogenation
Pt / Pd Pt / Pd
CH ≡ CH + H2 → CH2 = CH2 + H2 → CH3 - CH3
ethyne ethene ethane


































(b) Halogenation (X2)
ethyne chlo light bromine aqueous
liquid iodine ethanol
light light
CH ≡ CH + Cl2 → CHCl = CHCl + Cl2 → CHCl2 - CHCl2
ethyne ethyne dichloride ethyne tetra chloride
CH ≡ CH + Br2(l) → CHBr = CHBr + Br2 → CHBr2 - CHBr2
ethyne (reddish ethyne dibromide (reddish ethyne tetra bromide
brown) (colourless) brown) (colourless)
CH ≡ CH + Br2(aq) → CHBr = CHBr
ethyne (reddish ethyne dibromide
brown) (colourless)
ethanol
CH ≡ CH + I2 → CHI = CHI
ethyne ethyne diiodide
(c) Hydrohalogenation (HX)
CH ≡ CH + HX → CH2 = CHX + HX → CH2 -CHX2
ethyne vinyl halide ethylidene halide
3. Hydration (addition of water)
H 2SO 4
CH ≡ CH + H2O (dil) 2→ [ CH2 = CHOH ] → CH3- CHO
Hg + , 60 � c

ethyne vinyl alcohol (unstable) ethanal


O
H 2SO 4
CH3– C ≡ CH + H2O (dil) 2→ [ CH3 – COH = CH2] → CH3– C– CH3
Hg + , 60 � c

propyne propen-2-ol (unstable) dimethyl


ketone(acetone)
ethyne
60

(a) Substitution with sodium


Δ 1
(1) CH ≡ CH + Na → CH ≡ CNa + H
2 2
ethyne monosodium
(or) acetylene acetylide
Δ 1
CH ≡ CNa + Na → CNa ≡ CNa + H
2 2
monosodium disodium
acetylide acetylide


































Δ 1
(2) CH3-C ≡ CH + Na → CH3-C ≡ CNa + H
2 2
propyne (or) sodium
methyl acetylene methyl acetylide
Δ 1
(3) CH3-CH2-C ≡ CH + Na → CH3-CH2-C ≡ CNa + H
2 2
1-butyne (or) sodium
ethyl acetylene ethyl acetylide
Δ
(4) CH3-C ≡ C-CH3 + Na → no reaction
2-butyne (or) dimetyl acetylene
(b) Substitution with copper
1
(1) CH ≡ CH + Cu Cl + NH3 → CH ≡ CCu ↓ + NH4Cl
2 2 2
ethyne (or) acetylene monocopper(I) acetylide (red ppt)
1
CH ≡ CCu + Cu Cl + NH3 → CCu ≡ CCu ↓ + NH4Cl
2 2 2
monocopper dicopper(I)
acetylide acetylide (red ppt)
1
(2) CH3-C ≡ CH + Cu Cl + NH3 → CH3-C ≡ CCu ↓ + NH4Cl
2 2 2
propyne (or) copper(I)
methyl acetylene methyl acetylide (red ppt)
1
(3) CH3-CH2-C ≡ CH + Cu Cl + NH3 → CH3-CH2-C ≡ CCu ↓ + NH4Cl
2 2 2
1-butyne (or) copper(I)
ethyl acetylene ethyl acetylide (red ppt)
(4) CH3-C ≡ C- CH + Cu2Cl2 + NH3 → no precipitation
2-butyne (or) dimethyl acetylene
(c) Substitution with silver
(1) 2CH ≡ CH + Ag2O + NH3 → 2CH ≡ C Ag ↓ + NH4OH
ethyne (or) acetylene monosilver acetylide (white ppt)

2CH ≡ CAg + Ag2O + NH3 → 2CAg ≡ CAg ↓ + NH4OH


monocopper acetylide disilver acetylide (white ppt)

(2) 2CH3-C ≡ CH + Ag2O + NH3 → 2CH3-C ≡ CAg ↓ + NH4OH


propyne (or) silver methyl
methyl acetylene acetylide (white ppt)

(3) 2CH3-CH2-C ≡ CH + Ag2O + NH3 → 2CH3-CH2-C ≡ CAg ↓ + NH4OH


1-butyne (or) silver
ethyl acetylene ethyl acetylide (white ppt)
(4) CH3-C ≡ C- CH3 + Ag2O + NH3 → no precipitation
2-butyne (or) dimethyl acetylene


































Exercise
1. Complete the following reactons.

(a) CaO + C → ? (b) C aC 2 + H2O → ?


(c) CH ≡ CH + Cu2Cl2 + NH3 → ? (d) CH3-C ≡ CH + Cu2Cl2 + NH3 → ?
(e) CH3-C ≡ CH + Na → ? (f) CH3-C ≡ CH + Ag2O + NH3 → ?
(g) CH ≡ CH + Ag2O + NH3 → ? (h) CH ≡ CH + Cl2 → ?
(i) CH ≡ CH + H2O → ?

2. What happen when?

(a) ethene dibromide is heated with alcoholic KOH ?


(b) ethylidene chloride is heated with alcoholic potassium hydroxide ?
(c) propene di bromide is heated with alcoholic KOH ?
(d) calcium carbide is treated with water ?
(e) methyl acetylence is passed into ammoniacal silver oxide ?
(f) ethyl acetylence is passed into ammoniacal solution silver oxide ?
(g) ethyne(acetylene) is reacted with excess hydrogen in the presence of Pt or Pd ?
(h) calcium oxide is reacted with coke in the electric furnance?
(i) ethyne is reacted with chlorine in the dark by the presence of catalyst ?
(j) propyne reacts with excess hydrogen ?
(k) ethyne reacts with an excess of HBr ?
(l) reaction of 1-butyne with an excess of HBr?
(m)vinyl bromide react with HBr ?
(n) ethyne is passed into ammonical copper (I) chloride solution?
(o) methyl acetylene is passed into ammoniacal solution of copper(I) chloride?
(p) ethyne is passed into ammoniacal solution of silver oxide?
(q) acetylene is passed over heated sodium?
(r) methyl acetylene is passed over heated sodium?

3. Illustrate the following reactions.

(a) Dehydrahalogenation of ethene dibromide


(b) Dehydrahalogenation of ethylidene bromide
(c) Dehydrahalogenation of ethylidene chloride
(d) Substitution reacton of alkyne
(e) Acetylene preparetion from calcium carbide
(f) Substitution reaction of methyl acetylene
(g) Formation of silver acetylide

4. How would you prepare

(a) ethyne from carbon (b) ethyne from ethylidene chloride


(c) ethanal from ethyne


































5. Answer the following reactons.

(a) A gas '' X'' is obtained by heating a calcium carbide with water. What is gas '' X '' .
Write down the chemical equation.
(b) A gas '' X'' is obtained by heating ethylidene chloride with alcoholic potassim hydroxide.
What is gas '' X '' .Write down the chemical equation.
(c) A gas '' X'' is obtained by heating ethene dibromide with alcoholic potassim hydroxide.
What is gas '' X '' .Write down the chemical equation.
(d) A gas '' X'' is obtained by heating propene dibromide with alcoholic potassim hydroxide.
What is gas '' X '' .Write down the chemical equation.
(e) When gas A is passed into dilute sulphuric acid containing mercury (II) sulphate at 60 � C ,
the final product is ethanol . What is gas ''A''
(f) A gas ''B'' is liberated by passing propyne over heated sodium . What is gas ''B'' .
Write down the chemical equation.

6. How would you distinguish between the following pairs

(a) ethane and ethene (b) ethene and ethyne


(c) ethane and acetylene (d) propane and propene
(e) iso-butane and iso-butene (f) ethene and acetylene
(g) n-butane and 1-butyne (h) ethane and ethyne (by using ammoniacal
copper (I) chloride solution)
(i) 2-butene and 1-butyne (j) acetylene and dimethyl acetylene
(k) ethane and ethene (bu using %KMnO4) (l) 1-butyne and 2-butyne
(m) CH2 = CH2 and CH ≡ CH (n) ethylene and acetylene
(o) CH3-CH2-CH3 and CH3-C ≡ CH (p) methyl acetylene and dimethyl acetylene
(q) saturated hydrocarbon and unsaturated hydrocarbon

Alcohol

Alcohol equation

(I) Preparation of alcohol


(II) Chemical properties of alcohol

(I) Preparation of alcohol

1. Hydrolysis of alkyl halide


alkyl halide NaOH reflux ( Δ ) acohol NaX
reflux
(a) RCH2X + NaOH → RCH2OH + NaX
Δ

alkyl halide alcohol

reflux
(b) CH3-CH2Cl + NaOH → CH3-CH2OH + NaCl
Δ

ethyl chloride ethanol




































2. Manufacture of ethanol petroleum refinery products (ethanol from ethene)
(a) CH2= CH2 + H2SO4 → CH3-CH2HSO4
ethene ethyl hydrogen sulphate
(b) CH2= CH2 + CH3-CH2HSO4 → (CH3-CH2)2SO4
ethene ethyl hydrogen sulphate diethyl sulphate
(c) CH3-CH2HSO4 + H2O → CH3-CH2OH + H2SO4
ethyl hydrogen sulphate ethanol
(d) (CH3-CH2)2SO4 + 2H2O → 2CH3-CH2OH + H2SO4
diethyl sulphate ethanol
ethene ethanol product ethene
diethyl sulphate ethanol
3. Manufacture of ethanol by fermentation method
n malt n
(a) ( C6H10O5)n + H2O → C H O
2 diastase 2 12 22 111
starch maltose
yeast
(b) C12H22O11 + H2O → 2C6H12O6
maltase

maltose glucose
yeast
(c) C6H12O6 → 2CH3CH2OH + 2CO2 ↑
zymase

glucose ethanol
6 , 12 , 6 , 12 , 6 (d m z)
(II) Chemical properties of alcohols
1. Reaction with metallic sodium
1
CH3-CH2OH + Na → CH3-CH2ONa + H
2 2
ethanol sodium ethoxide
2. Reaction with PCl5
CH3-CH2OH + PCl5 → CH3-CH2Cl + POCl3 + HCl ↑
ethanol ethyl chloride
PCl5 ethanol OH
Cl POCl3 HCl

3. Reaction with sulphuric acid (H2SO4- 140 � C )


100 � C
CH3-CH2OH + H2SO4 → CH3-CH2SO4H + H2O
ethanol ethyl hydrogen sulphate
+
H
CH3-CH2OH + CH3-CH2SO4H → CH3-CH2-O-CH2-CH3 + H2SO4
ethanol ethyl hydrogen sulphate diethyl ether
140 - ethanol 100 � C product
product ethanol diethyl ether


































4. Esterification ( Formation of ester)
(a) Formation of organic esters
+
H
CH3CH2OH + CH3COOH → CH3COOCH2CH3 + H2O
ethanol ethanoic acid( acetic acid ) ethyl ethanoate(ethyl acetate)

H+ OH ethyl ethanoate

(b) Formation of inorganic esters


ZnCl 2
CH3-CH2OH + HCl → CH3-CH2Cl + H2O
ethanol ethyl chloride
CH3-CH2OH + HBr → CH3-CH2Br + H2O
ethanol ethyl bromide
CH3-CH2OH + HI → CH3-CH2I + H2O
ethanol ethyl iodide
5. (i) Dehydrogenation of alcohol
Cu ,300� C
CH3CH2OH → CH3CHO + H2
ethanol ethanal (acetaldehyde)
ethanol H2 300
(ii) Oxidtion of alcohol
K 2Cr2O 7
CH3CH2OH + [O] → CH3CHO + H2O
dilHSO 4

ethanol ethanal
K 2Cr2O 7
CH3CHO + [O] → CH3COOH
dilHSO 4

ethanal ethanoic acid


alcohol ethanol dichro
acid product / oxygen
Exercise
1. Complete the following reactons.
(a) CH3-CH2Cl + NaOH → ?
(b) CH3-CH2OH + HI → ?
(c) CH3-CH2OH + HCl → ?
(d) CH3-CH2OH + HBr → ?
(e) CH3-CH2OH + PCl5 → ?
(f) CH3-CH2OH + Na → ?
(g) CH3COOH + CH3CH2OH → ?
(h) (C6H10O5)n + H2O → ?
(i) C6H22O11 + H2O → ?
(j) C6H12O6 → ?
(k) CH3-CH2OH + Na → ?
(l) CH3-CH2OH + [O] → ?
(m) (CH3-CH2)SO4 + H2O → ?


































2. What happen when

(a) when ethanol is passed over freshly reduced copper at 300 � C ?


(b) maltose is treated with enzymase maltase?
(c) glucose is treated with zymase which is present in yeast?
(d) when ethanol is heated with concentrated sulphuric acid at 100 � C ?
(e) ethanol is heated with small amount of sulphuric acid at 140 � C ?
(f) ethyl hydrogen sulphate is treated with ethanol at 140 � C ?
(g) ethanol is treated with a mixture of potassium dichromate and dilute sulphuric acid?
(h) ethanol is treated with hydrogen chloride in the presence of anhydrous zinc chloride?
(i) the reaction of methanol with methanoic acid?
(j) PCl5 react with ethanol at room temperature?
(k) a piece of sodium is added to ethanol?
(l) methanol reacts with sodium?
3. Discuss the following reactions.
(a) Esterification ( formation of ester)
(b) Oxidation of alcohol
(c) Dehydrogenation of ethanol
4. Answer the following questions.
(a) When ethyl hydrogen sulphate is refluxed with an aqueous with an aqueous solution of
sodium hydroxide , compound X is formed . What is compound X? Write down the equation.
(b) Compound X can be formed by fermentation of glucose with enzyme zymase .What is
compound X ? Write down the equation.
(c) A compound X is obtained by passing ethene into cold dilute potassium permanganate
solution. What is compound X ? Write down the chemical equation.
(d) When a compound Z is treated with PCl5, ethyl chloride is obtained .What is compound Z.
Write down the equation.
(e) When phosphorus(V)chloride reacts with ethanol at room temperature a gas B is liberated.
What is the gas B? Write down the chemical equation.
(f) A compound X is obtained by the reaction of ethanol with HCl in the presence of anhy-
drous zinc chloride . What is the compound X ? Write down the chemical requation.
(g) Compound X undergoes esterification with ethanoic acid and the final product is ethyl
acetate . What compound X ? Write down the revant equation.
(h) A gas X can be formed by the hydrogenation of 2-butene using nickel catalyst at 300 � C .
Name the gas X. Write down the equation.
(i) A gas X can be obtained by hydrogenation of ethene using a nickel catalyst at 300 � C .What
is the gas X ? Write down the equation.
(j) A compound X is formed by passing ethanol over freshly reduced copper heated at 300 � C .
What is compound X? Write down the equation.
(k) A gas Z is liberated by adding a piece of sodium to ethanol at room temperature . What is
gas Z ?Write down the chemical equation.
5. Discuss the reaction of ethanol with
(a) ethanoic acid (b) PCl5
(c) H2SO4 at 140 � C (d) hot acidic potassium dichromate


































Petroleum Industry and pertrochemicals

Crude oil and other fossil fuels

(i) fossil fuels


(ii) the formation and fractional distillation of crude oil

(iii) catalystic cracking


(iv) alternative transport fuels
(v) coal
(vi) biogas

Fossil fuels
Fossil fuels were formed in the Earth's crust from material that once living.
There are there major fossil fuels;
(i) Coal
(ii) Crude oil (petroleum)
(iii) Natural gas
Coal - comes from fossil plant material.
Crude oil and natural gas are formed from the bodies of marine microorganisms.
* How are the Fossil fuels formed? What are the sources of coal,crude oil and natural gas?

non-renewable finite resources

Fuel (
A fuel is a substance which can be conveniently used as a source of energy.

* What is Fuel ?

Crude oil (petroleum)


Crude oil is one of the Earth's major natural resources. Crude oil is a mixture of
many different hydrocarbon molecules. Most of the crude oil is used to make fuel . Around
10% of crude oil is used as a feedstock, or raw material in the chemical industry.

* What are the Crude oil ?Explain its uses?




































Fractional distillationt
- Crude oil is a mixture of many different hydrocarbon molecules.
- At a refinery, crude oil is separated into different fractions consisting of groups of
hydrocarbons that have different bioling points by fracrional distallation .
- Separation of the hydrocarbons takes place in a fractionating tower or fractional
distillation column.
* Define the term fractional distallion.
* How would you separate the crude oil?
* What type of apparatus is used in this seperation?

molecules
molecules

Various crude oil Fractions


- The various crude oil fractions are
(1) refinery gas
(2) petrol(UK) or gasoline(USA) b . p and viscosity
(3) naphtha increasing
(4) paraffin(UK) or kerosene(USA)
(5) diesel oil
(6) lubricating oil
(7) bitumen residue
* What are the various crude oil fractions?
* Give the different terms used in UK of the following names gasoline and kerosene.

Cracking or catalytic cracking


- Larger molecules from the heavier fractions are broken down into smaller and more useful
molecules by the use of heat catalyst is known as cracking.
heat
eg. C10H22 → C8H18 + C2H4
catalyst

decane octane ethene

All cracking reactions gives two types of products -


(i) an alkane with a shorter chain than the original, and
(ii) a short-chain alkene molecule.

These two types of products are useful


-The shortened alkenes can be blended with the gasoline fraction to enrich
the petrol. The alkenes are useful as raw materials for making several
important products.
* What is catalytic cracking? What two types of products are given by all cracking reactions?
Mention their uses.


































Ethene from petrol (octane)
Pt
- octane (petrol) ethene + hydrogen

C8H18 4C2H4 + H2
Pt
- ethene + hydrogen → ethane
Pt
C2H4 + H2 → C2H6
* What an equation to indicate how petrol(ocatne) can be made into ethane.
Uses of diesel , kerosene and petrol
Diesel oil , kerosene , petrol
decreasing order of boiling piont
- Naphthas are used to make chemicals.
- Kerosene is used as a fuel in jet engines.
- Diesel oil is used as a fuel in diesel engines.
- Fuel oil is used as fuel for ships and for home heating systems.
- Gasoline is used as a fuel in cars(petrol).
* Express the uses of naphthas, kerosene , diesel oil , fuel oil and gasoline .
Biogas
- Biogas can be produce from cow dung and organic waste in the absence of air. It is the
mixture of methane and carbon dioxide produced naturally from the decay of organic waste in
the absence of air. ( anaerobic fermentation process)
Uses of biogas
- In Myanmar, biogas is used as a fuel for local industry and to powder the electricity
generating enegines.
* How is biogas produced ? Give the name of this reaction process.
What is biogas composed of ?
* What is biogas? Explain the use of biogas in Myanmar.
Different kinds of coal
(1) peat (not a coal)
(2) lihgnite ( brown coal)
(3) bituminous (soft coal)
(4) anthracite (hard coal)

* Two type of coal peat


* Write down the product of Anthracite(hard coal) from Peat (not a coal).
* Give the type of four steps in the coal-forming process.(OR) What are the different types
of coals.
Chemicals obtained from coal and their uses

- The chemicals which can be obtained from coal are ;


(1) Ammonia - for fertilizers
(2) Coal gas - for industrial heating
(3) Coal tar - for paint, dyes, creosote and pitch
(4) Coke - for iron and steel making and for home and industrial heating.
* Name the chemical which can be obtained from and mention their uses.


































Alternative transport fuels
Hydrocarbon (OR) Gasoline from methanol
ZSM _ 5
- methanol → hydrocarbon + water
n CH3OH → (CH2)n + n H2O

ZSM-5
- ZSM-5 is an artificial zeolite composed of aluminium, silicon and oxygen.

Zeolite
- A zeolite is one of a large group of alumino-silicates of sodium, potassium, calcium
and barium.
* What is zeolite?Explain the term ZSM-5 catalyst.Convert methanol to gasoline using zeolite.
Ignition temperature
- The ignition temperature is the temperature at which a fuel-air mixture ignites without a
flame. ( eg - for petrol it is 550 � C )
(- Ignition temperature

Flash-point
- The flash point is the temperature at which the vapour will ignite in air in the presence
of a flame. ( eg - for octane it is 13 � C )
(-Flash point
* Explain the terms ignition temperature and flash point.
* State the difference between the flash point and ignition temperature.

Long form of LPG and CNG and their uses


- LPG = liquid petroleum gas ( is composed of propane and butane)
- CNG = compressed natural gas ( is 90% methane)

Uses of LPG and CNG in Myanmar


- LPG is used in households, restaurants, hotels and motel for cooking, frying and other
heating system.
- CNG is used in taxis , buses and vehicles.
* What is the long form of LPG and CNG ? And mention their composition.
* What are the uses of LPG and CNG in Myanmar?

Knocking
- If the fuel ignites too easily then the engine will not run smoothly-knocking will occur.

Reforming
- High-quality petrol contains many branched-chain hydrocarbons, make in a process
known as reforming,so that does not ignite too soon.
-

reforming


































Tramsesterification (
-The plant or animal oil has to be converted to biodesel by the chemical process which is
known as tramsesterification.
-

First stage - Preparation of nearly 100% pure methanol or ethanol.


Second stage - The addition of potassium hydroxide or sodium hydroxide basic
catalyst to the prepared pure methanol or ethanol.
Third stage - The treatement of the seed oil with the prepared basic catalyst
solution and the solution is heated to 60 � C which is the
Transesterification process producing methyl or ethyl ester as the
product (biodiesel) of the reaction.
Fourth stage - The removal of glycerine and sodium of potassium salt of fatty acids
(soap) from the reaction mixture by washing with water and pure
biodiesel is separated out by using the biodiesel processor.

* Define the term Transesterification. There are four stages in the coverted of fats or oil to
biodiesel. Explain the final stage of this process.
*Give the name of the process which is used for conversion of biodiesel from used oil. Explain
the third stage conversion.

Source of biodiesel
- Plant and animal oil may serve as the source of biodiesel.

Biodesel
- It is derived from plant seed oil which can be used as a substitute for diesel fuel. The plant
seed oil has to be biodiesel by the chemical process known as biodiesel.

Uses of biodiesel
- In Myanmar, biodiesel is used to power tractor engines, petro-diesel engines, and electricity
generating engines. It is the potential substitue for petro-diesel.

Biomass
- Biomass is an organic waste.When it decays in the absence of air, methane is produced.
-The approximate composition formula of coal is C135H96O9NS.

Composition of car exhaust fumes


- Car exhaust fumes are composed of very little sulphur dioxide,carbon monoxide , unburnt
hydrocarbons(HC), and oxides of nitrogen(NOx).

* What is meant by the term biodiesel? What are the sources of biodiesel?
Explain the use of biodiesel in Myanmar.
What is meant biomass ? Give the approximate composition formula of coal.
* What are car exhaust fumes composed of ?



































Advantage of diesel engines
- Diesel engines are more efficient than petrol engines and produce less carbon monoxide.

Disadvantage of diesel engines


- Working temperature of diesel engine is higher , they produce more oxides of nitrogen. The
major problems are smoke and odour.

Fractionating tower or fractional distillation column





































Q. Petroleum (crude oil) is a mixture of several compounds which are separated in a refinery
by means of an apparatus as shown below.
(a) What is the name of the apparatus?
(b) What is the name of the process which is used in separating crude oil?
(c) On what physical property of the compounds in the mixture does teh separation depend?
(d) Use the letters A to G to describe where the following could be found.
(i) The fraction that represent gases. (ii) The fraction with the largest molecules.
(ii) The fraction that represent liquids with the lowest boiling point.

Ans; (a) fractional distillation column (or) fractionating tower.


(b) fractional distillation.
(c) The separation depends on boiling point.
(d) (i) A (ii) G (iii) B

******************************************************



































Staturated hydrocarbons
Alkanes are known as saturated hydrocarbon. They are represented by the general
formula,CnH2n+2 .

Unstaturated hydrocarbons
Alkenes and alkynes are are known as unsaturated hydrocarbon. They contain
unsaturated double bonds(alkenes) and unsaturated triple bonds(alkynes) respectively.

Homologous series
A series compounds like alkanes in which memver differ from the proceding or
succeeding one by a –CH2– group is known as the homologous series.

Structural Isomers
Compound having the same molecular formula but different structural fromulae have
different physical and chemical properties and are said to be structural isomers. The
phenomenon is known as structural isomerism.

**********************************************************

1. Write TRUE or FALSE for each of the following statements.

*1. Fossil fuels are renewable.


2. Fossil fuels were formed in the Earth's crust from material that was once living.
*3. Coal comes froms marine microorganisms.
4. Crude oil and natural gas are finite resources.
*5. Coal is a single substance.
6. Oil-fields and gas-fields are detected by a series of geological searches.
7. A fraction of petroleum contains different hydrocarbons with different bioling points.
8. The boiling points are roughly related to the number of carbon atoms in the hydrocarbon.
9. The demand of light fraction is greater than heavy.
10. The separation of different fractions depends upon the boiling points.
*11. Fractions from the top of the fractionating tower are called heavy.
12. Peat is the first step in the coal-forming process.
*13. The cracking of the molecule occurs at the fixed place.
14. Cracking of a large hydrocarbon molecule always produces smaller alkane and alkene
molecules.



































15. Knocking eill occur in gasoline engine.
16. Lignite is also known as ' brown coal'.
17. Diesel engines produces more oxides of nitrogen.
*18. Using lead in gasoline is harmless.
19. Anthracite is the hardest coal.
*20. Bituminous coal is limited supply in most areas.
*21. Ethene is accumulated in coal-mines.
*22. The flash point of a fuel is greater the nthat of ignition temperature.
23. The trade-name of polypropene is ' polypropylene '.
24. Fuels with low flash point is dangerous.
25. Butene polymerises to synthetic rubber.
26. Larger molecules from heacier fractions can be broken into smaller more valuable mol-
ecules.
27. Diesel engines are more efficient than petrol engines.
28. Tetraethyl-lead is added to gasoline to prevent ' knocking '.
29. The levels of toxic gases from car exhaust are reduced by using catalytic converter.
30. The major problems of diesel engines are smoke and odour.
31. If the dfuel ignites too easily, knocking will occur.
*32. Alkyne undergo only substitution reaction.
33. Greenhouse effect is due to the formation of methane naturally.
*34. The fuel with easily ignition operates the engine smoothy.
35. High-speed diesel engines use fuel contaning hydrocarbon molecules consisting of be-
tween 6 and 20 carbon atoms.
36. Diesel engenes are compression ignition engines.
37. High-quality petrol contains many branched-chain hydrocarbons.
*38. Kerosene(paraffin) and diesel are produced as light fraction in fractionating tower.
*39. Diesel engine produces more carbon monoxide than gasoline engine.
*40. Major constituent of CNG is propane.
*41. IUPAC name of acetaldehyde is methanal.
42. Plants and animals oil may serve as the source of biodiesel.
43.Formation of biogas is an anaerobic process.
44. Rapeseed plant, sunflower plant, palm oil plant are oil-producing crops.
45. Teh process of plant oils to biodiesel is called transesterification.



































3.Select the correct word(s), notation(s), term(s), unit(s) , etc given in the brackets.

1. [Alkanes; Alkenes; Alkynes] are saturated hydrocarbons.


2. [Alkyl chloride; Alkyl bromide; Alkyl iodide] is usually used to prepare an alkane by the
reduction with hydrogen.
3. Alkanes may undergo [addition; substitution; hydration] reactions.
4. The first four members of alkanes are [solids; liquids; gases].
5. The most reactive hydrogen halide to alkene is [HCl; HBr; HI].
6. Isomers of C4H10 is [h-butane and iso-butane; methyl proapne and iso-butane; butane and
butene].
7. Chlorination of [ethane; ethene; ethyne] is a substitution reaction.
8. Elimination of hydrogen and hydroxyl group from the two adjacent carbon atoms of an
alcohol is [hydration; dehydration; dehydrogenation] reaction.
9. The general formula for alkene is [Cn2n+2; CnH2n; CnH2n-2].
10. Methanal is formed when ethene undegoes [hydrogenation; hydroylation; ozonolysis].
11. The dehydrohalogenation of iso-propyl chloride gives [propane; propene; propyne].
12. [Alkanes; Alkenes; Alkynes] are unsaturated hydrocarbons.
13. An isomer of ethylene dichloride is [1, 1-dichloroethane; 1,2-dicholoroethane; ethylidene
chloride].
C
14. C=CH2 is (a saturated; an unsaturated) hydrocabon with the general formula of
C [CnH2n+2; CnH2n; CnH2n-2].
15. If [alkane; alkene; alcohol] is shaken with 1%Br2 solution, the bromine colour is discharged.
16. Alkynes contain [single bond; double bond; triple bond] between two carbon atoms.
17. [Alkanes; Alkenes; Alkynes] may undergo both substitution and addition reactions.
18. Hydration of [acetylene; ethene; ethane] gives acetaldehyde.
19. [1-butyne; 2-butyne; 2-butene] may undergo substitution reaction.
20. The name of methyl ethyl acetylene according to the IUPAC system is [3-pentene; 3-pentyne;
2-pentyne].
21. Starch is hydrolysed by [diatase; maltase; zymase].
22. Glucose is converted to ethanol by the enzyme [maltase; diatase; zymase].
23. Ethanol reacts with small proportion of concentrated sulphuric acid [100°C; 140°C; 160°C]
to give diethyl ether.
24. Raw materials for ethanol production are [ethane; ethene; starch].



































4.Match each of the items in List A with the approopriate irtem in List B.

List A List B

1. (a) General formula for ethene (iv) CnH2n


(b) isomer of 1, 1-dichloro ethene (iii) 1, 2 dichloro ethene
(c) Reduction (v) hydrogenation
(d) Hydration of ethyne (vi) ethanal
(e) Carbohydrate (ii) starch
(f) alkane (vii) Cn H2n+2
(g) ethanol (i) ethylalcohol

2. (a) acetaldehyde (vii) ethanal


(b) the toxic alcohol (v) methanol
(c) conversion of glucose to (i) fermentation ethaonl by yeast
(d) hydroxylation of ethene (iii) ethene glycol
(e) dehydration of ethanol (vi) ethene
(f) alkenes and alkynes (iv) unsaturated hydrocarbon
(g) Alkyne (ii) CnH2n-2

3. (a) Alcohol (ii) CnH2n+2O


(b) Ether (iv) same general formula with alcohols
(c) aldehyde (vi) -CHO
(d) organic acid (v) R-COOH
(e) ethyl ethanoate (vii) an ester
(f) formaldehyde (iii) methanal
(g) ethylidene chloride (i) 1, 1-dichloroethane

4. (a) ethyl ether (v) (CH3-CH2)2O


(b) methyl ethyl ester (iii) ethyl ethanoate
(c) diastase (i) break down the starch
(d) maltase (vi) break down maltose
(e) zymase (iv) convert glucose to ethanol
(f) starch (ii) (C6H10O5)n



































2.Fill in the blanks with the correct word(s), phrase(s) term(s), unit(s) etc.

1. Carbon has 4 valence electrons.


2. The bond order of hydrogen is 1 (one).
3. Orgenic chemistry is the chemistry of carbon compounds in which there is at least one
carbon to carbon bond or carbon to hydrogen bond.
4. The general formula of alkene is CnH2n.
5. Alkanes are represented by general formula CnH2n+2.
6. Alkanes may undergo substitution reactions.
7. The general formula for an saturated hydrocarbon is CnH2n+2.
8. Alkanes are saturated hydrocarbon.
9. First four members of alkanes are gases.
10. The general formula for alkyne is CnH2n-2.
11. The general formula for alcohol is CnH2n+1OH.
12. Heating of sodium ethanoate with soda lime gives methane.
13. Methane and chlorne will give substitution reaction in diffused sunlight.
14. Alkyl iodide us usually used to prepare an alkane by the reduction with hydrogen.
15. Colour of bromine solution may be discharged by passing it throug alkene.
16. Ethene is used for ripening fruits.
17. Hydrogen on triple bonded carbon can be replaced with metal.
18. Ethyne and ethene can be distinguished bu using KMnO4 solution.
19. Methanol, CH3OH is also called methyl alcohol.
20. Dehydrogenation of ethanol gives ethanal.
21. Removal of water from alcohol is called Dehydration.
22. Starch is hydrolysed by diastase.
23. Moltose is hydrolysed by moltase.
24. Glucose is decomposed by zymase.
25. Sugar is a compound of carbon, hydrogen and oxygen.
26. Hydrogenation of ethene gives ethane.
27. Hydration of ethyne gives ethanal.
28. Hydration of acetylene or ethyne.
29. Hydrogenaion of ethanol with concentrated H2SO4 at 160°C gives ethene and water.
30. Heating of ethanol with concentrated sulphuric acid at 140°C gives diethylether.
31. Heating of ethanol with concentrated sulphuric acid at 100°C gives ethyl hydrogensulphate
and water.
32. Calcium carbide is treated with water to liberate ethyne.
33. Unsymmetrical alkenes give two products by the reaction with unsymmetrical addendum.
34. Hydrohalogenation reaction is the addition of HCl to alkene.
35. Alkenes containing more than sixteen carbon atoms are solids at room temperature.
36. The IUPAC name for isobutylene is 2 methyl-propene.
37. The IUPAC name of dimethyl acetylene is 2 butyne.
38. The IUPAC name for CH3-CH=CHCH3 is 2 butene.



































CH3
39. The IUPAC name of CH3-C-CH=CH2 3 methyl-1-butene.
CH3
40. The IUPAC name of CH3 � C-CH-CH3 3 methyl-1-butyne.
41. The IUPAC name of acetic acid is called ethanoic acid.
42. The name of methyl ethyl acetylene according to the IUPAC system is 2-pentyne.
43. The radicals derived from alkanes are called alkyl radicals.
44. Formaldehyde is also called methanal.
45. Several compounds present in crude oil (petroleum) are separated in a refinery bymeans of
an apparatus named as fractionating column.
46. Petroleum is a complex mixture of hydrocarbon molecules.
47. Petroleum is composed of compounds of carbon and hydrogen.
48. Petroleum is a fossil fuel and was formed millions of years ago from dead bodies of marine
microorganisms.
49. Crude oil is one of the Earth's major natural resources.
50. Crude oil and natural gas are formed from the bodies of marine microorganisms.
51. Variation in gravity and magnetic field can also give cluses. Finally, a seismic survey is
carried out.
52. Crude oil is a mixture of many different hydrocarbon molecules.
53. Most of the crude oil that is extracted from the ground is used to make fuel, but around
10% is used as a feedstock.
54. The various hydrocarbon molecules are separated by refining.
55. Separation of the hydrocarbons takes place in a fractional distillation column, or fraction-
ating tower.
56. The individual single hydrocarbons can then be obtained by further distillation.
57. Larger molecules from these heavier fractions can be broken into smaller and more valu-
able, moleucles and this processes is called catalytic cracking.
58. All cracking reactions give two types of products.
59. An important consideration show easily the fuel vapour ignites.
60. High quality petrol contains many branched-chain hydrocarbons, make is a process known
as reforming.
61. The flash-point is the temperature at which the vapour will ignite in air in the presence of a
flame.
62. The methanol produced is then turned into hydrocarbons using the ZSM-5 catalyst.
63. Diesel, containing hydrocarbon molecules consisting of between six and 20 carbon atoms.
64. The major problems of diesel are smoke and odour.
65. Liquid petroleum gas (LPG) is composed of propane and butane.
66. Compressed natural gas (CNG) is composed of 90% methane.
67. In Myanmar, CNG supply of natural gas from Yetagun and Yadana Offshore Natural Gas
Oil Enterprise.
68. Methane is produced from orgainc waste biomass when it decays in the absence of air.
69. Methane is useful for heating and cooking, and the solid residue is used as a fertilizer.



































70. The main source of biodiesel is from jactrova plant seed oil.
71. The seed oil has to be converted to biodiesel by the chemical process known as
transesterification.
72. The potential for adding plant oils to diesel fuel is being investigated word-wide.
73. Coal is our most abundant fossil fuel.
74. Coal comes from fossil plant material.
75. Coal is not a single substance.
76. Peat is the first step in the coal-forming process.
77. Anthracite is the hardest coal, with the highest carbon content.
78. With heat and pressure over a long timescale, it first forms lignite, and then the
harder types of coal.
79. Plant and animal oil may serve as the source of biodiesel.
80. Biogas is a mixture of methane and carbondioxide.
81. Biogas forms as the rubbish decays.
82. In some parts of Myanmar, biogas has been generated from cow dung.
83. Many villages in Myanmar such as villages in kyauke township have electricity
supply from generating engines powered by biogas.
84. Tetraethyl lead is added to gasoline to prevent knocking.

* * * * * * * * *

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