1

1.
Ni, Pd , Pt

C2 + 2 C2+2
2. (Cl2, Br2, I2)
CCl

4 CvH2vBr2

CvH2v + Br2
3. (HCl, HBr, HI)

CvH2v + HCl CvH2v+1Cl

+

( Markovnikov)
C3 C2CH CH3

C3 C2CH = CH2 + H Cl

Cl
4. 2
CvH2v + H2O
+

C3 C2CH = CH2 + H OH

2 SO4
H

CvH2v+1OH

( Markovnikov)
C3 C2 CH CH3

H2SO4

) C C
5.
Ni, Pd , Pt

CvH2v2 + 2H2 CvH2v+2

6. (Cl2, Br2, I2)
CvH2v2 + 2 Cl Cl CvH2v2Cl4
7. (HCl, HBr, HI)
CvH2v2 + 2HCl CvH2vCl2
Cl
C3 C2C CH + HCl

C3 C2C = CH2
|

Cl
8. 2
Cv H2v2 + H2O

H SO

HgSO4

CvH2vO

+ HCl

C3 C2C CH3
|

Cl

H SO

2
C3 C2C CH + H2O
4

C3 C2C = CH2

C3 C2C CH3

HgSO4

||

OH

>C = O

9.
Ni, Pd , Pt

CvH2vO + H2 CvH2v+1OH
C3 C2CH = O + H2

Ni

C3 C2CH2 OH

10.
CvH2vO + HCN CvH2v(OH)CN
CvH2v+1CH = O + HCN CvH2v+1CH(OH)CN
C3 C2CH = O + HCN

C3 C2CH CN

OH
11. Grignard
HCH = O + C2+1MgCl

CvH2v+1CH2gCl

CvH2v+1CH2
1

g()Cl

CvH2v+1CH = O + C2+1MgCl

CvH2v+1 CHCH2+1
|

gCl
C2+1

C2+1
|

CvH2v+1 C = O + C2+1MgCl

OH
H

CvH2v+1 C CH2+1
|

gCl

+
H OH

CvH2v+1 CHCH2+1

g()Cl

H
2

C3 CH = + C3 C2MgBr

..............................
.....

.................

CvH2v+1 C CH2+1
|

+
H OH

............

Mg(OH)Cl

+
H OH

Mg(OH)Br

C3

.....................
.

C3 C =
+ C3 C2CH2MgI

g()Cl

C = + C3 C2CH2MgCl

C2+1

+
H OH

...............

OH
H

Mg(OH)I

............

| |
C C C=C +AB
| |
A B
( Saytzeff) 3>2>1.
12.
C H OH /

2 5
CvH2v+1Cl + KOH

CvH2v + KCl + 2

CH3 CH2 CH CH3 + KOH

C H OH /

2 5

Br

CH3CH = CH CH3 + KBr + 2

2 ( )

13.
C H OH /

2 5
CvH2vCl2 + 2KOH

CvH2v2 + 2KCl + 22

CH2 CH C3 + 2KOH
|

Cl

Cl

C H OH /

2 5

C CCH3 + 2KCl + 22

14.
H SO

> 170o C

2
CvH2v+1OH
4 CvH2v + 2

CH3

CH3

CH3 CH C CH2CH3
|

H SO

> 170 C
o

CH3 C = C CH2 CH3 + H2O

15.
+

HO

2
C 2 +1 X + N+OH

C2+1 OH + X

C3 C2Cl + OH ( /) C3 C2OH + Cl

16.

RON
+

C 2 +1 X + C2+1 + C2+1 O C2+1 + N

C3 C2 Cl + CH3CHON

C3 C2O CHCH3

17.

CH3
RCOO
+

CH3

C 2 +1 X + C2+1COON C2+1 COO C2+1 + X

CH3Cl + C3 C2COON C3 C2COOCH3 + NCl

18.

NH3
+

C 2 +1 X + NH2 C2+1 NH2 + HX

C3 C2CH2Cl + NH3 C3 C2CH2NH2 + HCl

19.

(CN KCN)
+

C 2 +1 X + + C C2+1 C N + N
C3 C2CH2Cl + CN C3 C2CH2CN + Cl
20.
+

CvH2v+1CN + 2H2O

CvH2v+1COH + 3

.. C3 C2 C N + 2H2O

CvH2v(OH)CN + 2H2O

H+

H+

C3 C2COOH + NH3

CvH2v(OH)COOH + NH3

CH3 CH2CHCN + 2H2O

H+

CH3 CH2CHCOOH + NH3

OH
2

OH
2
21. RC C
+

C 2 +1 X + C2+1 C C N+ C2+1 C C C2+1 +

CH3Cl + CH3C C CH3C C CH3 + NCl

22. (R
OH)
CvH2v+1OH + SOCl2 CvH2v+1Cl + SO2 + HCl
CH3CHCH3 + SOCl2 CH3CHCH3 + SO2 + HCl (2 )
|

OH

Cl

(RCOOH)
(RCOOR)
23.
O

||

||

C2+1 COH + C2+1 OH

C2+1 CO C2+1 + 2
+

CH3 CH2COOH + CH3 CH2OH

24.
O

CH3 CH2COOCH2CH3 + 2

||

C2+1 CO C2+1 + H

||

C2+1 CO + C2+1
+

CH3COOCH3+ H

CH3COO +

CH3

25.
C2+1 C C2+1

C2+1 OH + C2+1 C
( )

CH3CCH2CH3 + CH3C + CH3CH2OH

26. ()

CvH2v+2 + X X CvH2v+1X + HCl

.. CH3 H + Cl Cl CH3 Cl + HCl

27.
v C2 = C2 (CH2 CH2)v

v C2 = C

(CH2 CH)v

CH3

CH3

v C2 = C

(CH2 CH)v (PVC)

Cl

Cl

v C2 = C

(CH2 CH)v

C6H5

C6H5

C6H5

v C2 = C

(CH2CH)v

28.
N
(CH2C=CCH2)v
vCH2=CHCH=CH2

BuN
1,3
vCH2 = C CH = CH2

(
)

(CH2 C = CH CH2 )v

( )

CH3

CH3

21,3
v CH2 = CH C = CH2 ( CH2 CH = C CH2 )v
|

Cl
21,3

Cl

1,3

CH2 = CH

: Buna S

C6H5
1,3

CH2 = CH - C

: Buna

|O | :
1 : CvH2v+1CH2OH + |O| CvH2v+1 CH=O + 2
CvH2v+1CH2OH + 2|O| CvH2v+1 CO + 2
2 :

CvH2v+1CH C2+1 + |O|

CvH2v+1 C C2+1 + 2

||

KMnO4 K2Cr2O7
29. KMnO4 :
+3

5 CH3 C H2OH + 4KMnO4 + 6H2SO4 5 CH3 C OH + 4MnSO4 + 2K2SO4 + 11H2O

30. K2Cr2O7 :
+1

3CH3 C H2OH + K2Cr2O7 + 42SO4 3CH3 C H2OH + Cr2(SO4)3 + K2SO4 + 7H2O

KMnO4 :
0

+2

5 CH3 C H-CH3 + 2KMnO4 + 32SO4 5 CH3 C CH3 + 2MnSO4 + K2SO4 + 8H2O

|

||

OH

K2Cr2O7 :
+2

3 CH3 C HCH3 + K2Cr2O7 + 42SO4 3 CH3 C CH3 + Cr2(SO4)3 + K2SO4 + 7H2O

|

||

OH

31. CO2 (
)
+2

+4

5 C OH + 2 KMnO4 + 32SO4 5 C O2 + 2MnSO4 + K2S4 + 8 H2O

32. CO2 : (
)
+3

C OO
|

C OO
5

COO
|
COO

+4

+ 2nO4 + 32SO4 10 C O2 + 2nSO4 + K2SO4 + 8H2O

+ 2nO4 + 82SO4 10CO2 + 2nSO4 + K2SO4 + 52SO4 + 8H2O

( Tollens Fehling)
33. Tollens
+1

+3

CvH2v+1 C H = O + 2AgNO3 + 3NH3 + H2O CvH2v+1 C OONH4 + 2Ag + 2NH4NO3

+1

+3

CH3CH2 C H = O + 2AgNO3 + 3NH3 + H2O CH3 C OONH4 + 2Ag + 2NH4NO3

34.
+1

+3

CvH2v+1 C H = O + 2CuSO4 + 5NOH CvH2v+1 C OON + Cu2O + 2N2SO4 + 3H2O

+1

+3

CH3 CH2 C H = O + 2CuSO4 + 5NOH CH3 C OON + Cu2O + 2N2SO4 + 3H2O

,
.( )
35. CH3 C + 2 H2

CH3 C H2 H2

,
36. : CH2v+1COOH + N CH2v+1COON + 2
CH3 CH2COOH + N CH3 CH2COON + 2

37. : CH2v+1OH + N CH2v+1O + 2

CH3 CH2OH + N CH3 CH2O + 2
38. :

C6H5OH + N C6H5 O + 2

:
39. CH2v++1C CH + N CH2v++1C C N + 2
CH3 CH2C CH + N CH3 CH2C C N + 2
( 1 )
C CH + 2 C C + 2
40. CH2v++1C CH + CuCl+
+NH3 CH2v++1C CCu + NH4Cl
CH3 C CH + CuCl+ NH3 NH4Cl + CH3 C CCu
C CH + 2 CuCl + 2 NH3 2 NH4Cl + Cu C C Cu

( : , )
41. : CH2v+1COOH + CH2v+1COON + 2O
.. CH3 CH2COOH + CH3 CH2COON + 2O

C6H5COOH + N C6H5COO + 2
42. :

C6H5OH + NOH C6H5 O +2

(2CO3 NCO3 )

43. :
2 CH2v+1COOH + 2CO3 2 CH2v+1COON + CO2 + 2
2 CH3 CH2COOH + 2CO3 2 CH3 CH2COON + CO2 + 2
C6H5COOH + 2CO3 C6H5COO + CO2 + 2


44. (3)
:
CH2v+1 COOH + 3 CH2v+1COON4
.. CH3 CH2COOH + 3 CH3 CH2COON4

10

45. (RO) .
:
(RON) (RO) + 2
+

C2+1 O N+ + H OH

CH3CH2 O N+ + H OH

C2+1 OH + N
CH3CH2 OH + N

46. Grignard + 2
C2+1gX

HOH C2+2 + g(OH)X

CH3CH2CH2gCl + HOH

CH3CH2CH3

g(OH)Cl

47.
+ 2
CH2v+1C C N + HOH CH2v+1C CH +
CH3 C C N + HOH CH3 C CH +
( )
48. +
CH2v+1NH2 + HCl C2+1 NH3+ Cl
CH3NH2 + HCl CH3NH3+ Cl

(CH3)2NH + HCl (CH3)2NH2+ Cl

(CH3)3N + HCl

(CH3)3NH+ Cl

49. (RCOON) (RCOO) +

C2+1 COO+ + HCl C2+1 COOH + Cl

11

50.
CvH2v+1 CH CH3

v 1

OH

CHX3
CHCl3

Br2
CHBr3

v = 0 CH3CH2OH

2
CHI3
( )

CH3 CH CH3

Cl2
+

Cl2

CH3 C CH3 +

C C

CH3 C CH3

2HCl

||

+ 3Cl2

CH3 C CCl3 + 3HCl

||

||

CH3 C CCl3 + CH3 C O + CHCl3

||

5Cl +

||

5Cl

5H2O

CH3 CH CH3 + 4Cl2 + 6 CH3COO + CHCl3 + 5Cl + 5H2O

OH

: CvH2v+1 CH CH3 + 4Cl2 + 6 CH3COO + CHCl3 + 5Cl + 5H2O

|

OH
.. CH3CH2 + 4Cl2 + 6 COO + CHCl3 + 5Cl + 5H2O

CH3CHCH3 + 4Br2 + 6 CH3COO+ CHBr3 + 5Br + 5H2O

|

OH
CH3CH2CH CH3 + 4I2 + 6 CH3CH2COO + CHI3 + 5I + 5H2O
|

OH
51.
CvH2v+1 C CH3

v 1

||

v = 0 CH3CH=

Cl2
+
Br2
2

CHX3

CHCl3
CHBr3
CHI3
( )

12

CH3 C CH3 +

CH3 C CCl3 + 3HCl

||

CH3 C CCl3 +

C C

3Cl

3Cl2

||

CH3 C O + CHCl3

||

||

3Cl +

3H2O

CH3 C CH3 + 3Cl2 + 4 CH3COO + CHCl3 + 3Cl + 32

||

CvH2v+1 C CH3 + 3Cl2 + 4 CH3COO + CHCl3 + 3Cl + 32

||

CH3CH= O + 3I2 + 4 HCOO + CHI3 + 3I + 32

CH3CH2 C CH3 + 3Br2 + 4 CH3CH2COO+ CHBr3 + 3Br + 32

||