Вы находитесь на странице: 1из 17

O

O
R C

R C

R'

C= -

C O
C O

H
C O
H

(,
)

(,
)
O
H3C C CH3

()

H3C CH2 C

H 3C C

O
H3C C CH2 CH3

()

(
)
O
H3C C CH2
-2

H3C
H

H3C

CH2

CH2

CH3

O
C CH2

CH3

-3
O
C

..,

..,

-92

-21

-123

21

-81

49

-95

58

-86

80

-2

-78

102

-2

-57

128


1.
R CH2OH

[O]

OH
CH

O
R C
H

[O]

R
R'

O
C

R
R'

[O] - : Na2Cr2O7 , CrO3 , KMnO4 , MnO2 , Cu .

H3C CH2OH

CH3CH2 CH2OH
-1

H3C

OH
CH

Cu , 300oC
- H2
CrO3 , H2SO4

H3C C
H

( )
O

CH3CH2 C
H

Na2Cr2O7
CH3

H3C

O
C

CH3

( )

()

-2

2.

Cl
H2O
H3C CH2 CH
- 2HCl
Cl
1,1-

Hlg
R C R'
Hlg

H2O
R

- 2HHlg

O
C

R'

R, R' = H, Alk, Ar
Hlg = Cl, Br, I

O
H3C CH2 C

Br
H2O
H3C C CH2 CH3
- 2HBr
Br
2,2-

O
H3C C CH2

CH3

3.
R''

R'
C C
R

R'''

O3

R' O O R''
C
C
O
R'''
R

Zn, H2O,
CH3CO2H

R'

R''
C O

O C

R'''
R

5

4. ( )
R C C R' + H2O

HgSO4 , H2SO4

O
R C
H2C R'

5.

O
H3C CH2 C

Ca(OH)2

- 2 H2O
OH

H3C
H3C

O
H2
C C
O
Ca2+
O
C C
H2 O

to
-CaO, - CO2

H3C CH2
C O
H3C C H2
-3 (C5)


(C6)


1.
O

[H]

R C

R CH2OH

[H]
C O

R'

R
CH

OH

R'

[H]: H2/Pt(Pd, Ni); NaBH4 ( ); LiAlH4 ( )

2.
O

Zn, HCl

CH2CH2CH2CH3

CH2CH2CH3

H2N NH2
KOH
to

N NH2

KOH
to

2.

R C
H

[O]

R C

OH

[O]: Na2Cr2O7 , CrO3 , KMnO4 , H2O2 , Ag2O .


( : AgNO3 )
O

O
+ 2 Ag(NH3)2OH

R C
H

+ NH3 + H2O + 2 Ag

O NH4




R C

:
CuSO4 - Cu2+
O

O
R C

+ 2 Cu2+ + NaOH + H2O

+ 4 H+ +

R C
O Na+

Cu2O

3.
,
- .
2-3
H3C COOH + HOOC CH2CH2CH3
H3C
1

O
C CH2

CH2

CH2
5

CH3

KMnO4
to

3-4

-3

CH3CH2 COOH + HOOC CH2CH3

4. .
O
Ph C

KOH, H2O

O
Ph CH2OH + Ph C
O K+

Ph =

O
Ph C
H

O
OH

H
Ph C OH
O
O

Ph CH2OH + Ph C

Ph C
H

O
Ph C

+
O H

Ph CH2O

(1826-1910),

.
9

4. (AdN)

H+
C O + Nu

4.1.

C OH
Nu
R
R' C C N
OH

R
C O + H C N
R'

4.2.
R

C O + R''

MgHlg

R'
R
C O +
R'

R''

Li

R'
R C OMgBr
R''
R'
R C OLi
R''

H2O
- LiOH

H2O
- Mg(OH)Br

R'
R C OH
R''

R'
R C OH
R''

10

4.3.
R
R' C SO3Na
OH

R
C O + NaHSO3
R'
H
R
C O +
R'

O
S O Na+
O

R
R' C SO3Na
OH

4.4. PCl5
R
C O + PCl5
R'

R'

R
C Cl + POCl3
Cl

11

4.5.
R
C O + H2N R''

H+

R
C N
R'

R'

+ H2O

R''


R
C O +

H2N R''

R'

O H
R C N R''
R' H

OH
R C N R''
R' H

H+

H
O
R C N R''
R' H

R
- H2O

R C N R''
R' H

-H

C N
R'

R''

12


H3C

H3C
C O + H2N H
H3C

C N +
H3C
H

H2O

H3C

H3C

C N

C O + H2N CH3
H3C

H3C

H2O

CH3

H3C

H3C

C O + H2N OH
H3C

C N +
H3C
OH

H3C

H3C
C O + H2N NH2

H3C

C N +
H3C
NH2

H2O

H2O

H3C

H3C

C N

C O + H2N NH
H3C

H3C

H2O

HN

13

4.6.
O
R C

HO R'

H+ HO-

OH
R C OR'
H

HO R' H+

OR'
R C OR'
H

+ H2O

H+ HO-

OH
R C OR'
R

HO R' H+

OR'
R C OR'
R

+ H2O

O
C

R
R

HO R'

H+

C O
R

R
C O H

R
OR'
R C OH
R
OR' H
R C O
R R'

HO R'
C O H

R
H+

- H+

OR' H
R C O
R H
OR'
R C OR'
R

- H2O

R'

O
R C OH
R

OR'
R C
R

- H+

HO R'

14

5. - .

5.1.
. -
H
O
C C

B ()

C C

C C

- BH
-

-B
C-

OH

BH

C C


H
O
C C

H+

H
O H
C C

OH
+

C C

-H

15

OH

H3C C
H

H3C

O
C

. =

H2C C
H

OH
C
CH2
H3C

CH3

[]
= 2.0 10-5
[]

. = 1.5 10-7

5.2.
O
H 2C C
R'
R

Hlg2 (H+ HO )
- HHlg

Hlg
O

CH C
,
R'
R
--

O
H3C C

O
+

Br2

CH3

H2C C
+
CH3
Br
-

HBr
16

5.3.

(1833-1887),

.

..
O
O
H3C C

OH

H
- H2O

H3C C
H

H2C C
H
-

O
H3C C
H

CH2

H2O

- -OH

-
OH
H3C C CH2
H

C
H

OH

- H2O

(-)

OH
H3C C CH
H

O
C

- -OH

H3C C
H

C C
H H

17