(, , )
, , 2,
1) :
..
2) : 
-, 
-, 
-, 
-, 
- .
3) : - , , .
, (-, -, ). ( ), ( ). ,
| CH2Cl-COOH | 2- | |
| CCl3-COOH | 2,2,2- | |
| CH3CHOH-COOH | - ()
| 2- |
| HOOC-CHOH-CHOH-COOH | , /- ()
| 2,3- |
| CH2NH2-COOH | () | 2- |
I
1)
CH3-CH2-CH-COOH
O Cl
CH3-CH2-CH2-C +Cl2- CH3-CH-CH2-COOH
OH Cl
CH2-CH2-CH2-COOH
Cl
, -, -, - -.
2.
O O
CH3-CH-C + 2HOH 2HBr + CH3-CH-C
Br Br OH OH
O O
CH3-CH-C + 3NH3 NH4Cl + CH3-CH-C
Cl OH NH2 ONH4
3. - NH3
O O
CH3-CH=CH-C + HCl CH3-CH-CH2-C
OH OH OH
-
O O
CH2=CH-C + HNH2 CH2-CH2-C
OH NH2 OH
-
II. - -
OH
CH3-CH2-C=O + HCN CH3-CH2-C-C 
N
CH3 2HOH CH3 +NH3
OH O NH2
CH3-CH2-C-C + H3 CH3-CH2-C-C N + H2O
CH3 OH CH3
-- - +2 HOH
NH2 O
CH3-CH2-C-C + NH3
CH3 OH
2--2-
III. -
)
O COOC2H5 OH COOC2H5
H3-C + CH2 CH3-C-CH 
H2O +
H COOC2H5 H COOC2H5
COOC2H5
+ CH3-CH-CH 
2 C2H5OH + CO2 + CH3-CH-CH2-COOH
NH2 COOC2H5 NH2
) - g -
O O CH3-C-H OMgCl O
|
|
|
CH2-C + Mg CH2-C CH3-C-CH2-C
Cl OC2H5 MgCl2 OC2H5 H OC2H5 OH
OH O
CH3-CH-CH2-C
-MgCl(OH) OH
-C2H5OH
3-
IV.
, 3- 4- . R. CCl4 ( ).
O
CH2Cl-(CH2)5-CCl3 
CH2Cl-(CH2)5-C
+NH3 -4HCl -3HCl, -HOH +HOH -HCl OH
+3HOH -HOH
O O
CH2NH2-(CH2)5-C CH2OH-(CH2)5-C
OH OH
V. - .
|
+NH2OH 
| 
|
 H2O+
| 
| ||||
|
| 
| 
| 
| ||||
-
VI.
20 . () .
. . . . .
- . , .. . . ( ).
(2500 ), .
| , 0 | |
| H3COOH | 16,6 |
| CH2-COOH NH2 | 233 |
( )
O
CH2-C
NH3+ O-
( NH2).
, , . .
I.
1) ( )
( ) .
) , F>Cl>OH.
) , . ,
| CH2FCOOH | 2,1.10-2 |
| O CH2OH-C OH | 1,4.10-4 |
| CH2OH-CH2-COOH | 3,0.10-5 |
| CH3COOH | 1,7.10-5 |
. NH2 , , , .
2)
, , . - .
|
|
|
(, - Cu(OH)2), ( ), .
3) , , , (. ).
II. , , NH2-
1) , , , NH3, ROH, . - (. ).
2) , , , (. ).
3) NH2 , , HNO2 (. ).
III.
1)
-, , , . .
) - - 2-
O O
CH3-CH-C CH3-CH-C
OH OH O O
HO OH C-CH-CH3
C-CH-CH3 O
O
O
CH2-C CH2-C=O
NH2 OH HN NH
HO NH2 C-CH2
C-CH2 O
O
) - - , NH3.
- .
) --, - -
O CH2-CH2
CH3-CH2-CH2-C CH2 C=O
OH O
CH2-CH2-CH2-C=O CH2-CH2
NH2 OH CH2 C=O
NH
2)
( ) .
) (OH-)
CH3-CH-COOH + O 
CH3-C-COOH
OH O
) - -
H O H O O
CH3-C-C CH3-C + H-C 
HO-C CO2 + H2O
O-H OH O OH OH
O OH
CH3-C
O
3)
H H O
CH3-C-COOH CH3-C + HC CO + H2O
OH t O OH
O OH O O O O O
C-CH2-C-CH2-C C-CH2-C-CH2-C 2CO2 + CH3-C-CH3
COOH OH HO OH
+ HCOOH H2O + CO
16
, . , , . , . . .
, , . . .
, . , , .
- , , , .. 4- .
, .. , .
|
|
|
, , ( ).
--, --, - . ,
H O
CH3-C*-C
OH OH
COOH COOH
HO-C-H H-C-OH
CH3 CH3
, . - , 3 , . , . , , . .
COOH COOH
H OH OH H
CH3 CH3
(+) L(-)
d l, dextro laevo . , .. . D L.
D- , .
O
C
H
H-C-OH
CH2OH
, , , . , (+) (-). . , :
, , . D- L-. .
.
- .
, - , . ,
H O
CH3-C-C 50%
Cl OH
CH3-CH2-COOH + Cl2
-HCl Cl O
CH3-C-C 50%
H OH
. :
1) , ( 1848 , );
2) , () - , , .
3)
N=2n,
N- ;
n- .
HOOC-CHOH-CHOH-COOH
COOH COOH COOH COOH
H OH HO H H OH HO H
H OH HO H HO H H OH
COOH COOH COOH COOH
III IV I II
D- L-
. N=22=4. , (III) (IV). (IV) (III). (IV) 1800, (III), .
|
|
|
.
(I) D-, ; (II) . (III) (IV) , . , . . .
D- ( ). .
L- , D-.
, NaOH. , .
. D- L-. (=2040, ). , , .
.
