5

5.1.
1- 51
.
1.
:
.
.
.
. .
2. C-Br
CH3CH2Br :
H
|

. CH 3 C +
|

H
|

. CH 3 C
|

. CH 3 C
|

. CH 3 C
|

3. C-MgCl CH 3 CH MgCl
|

CH 3
:
.
.
.
. .
4. C-H 2,-

:
.
.
.
.
C .

116

5. :
CH 3 CH Cl + AgOH CH 3 CH OH + AgCl
|

CH 3

CH 3

CH 3 CH MgCl + 2 CH3-CH2-CH3 + Mg(OH)Cl

|

CH 3
:
H

CH 3 C

. CH3 C
|

. CH 3 C

. CH 3 C

CH 3

CH 3 C

CH 3

CH3

CH 3 C
|

CH 3

CH 3
H

H
|

. CH 3 C

CH 3 C

CH 3

CH 3

CH 3

6. CH3-CC-CH3 (I), CH3-CH2-CCH (II),

CH3-CH2-OH (III) CH3-CH2-ONa (IV)
i) :
. (II)

. (I), () (IV)

. (I) (II)

. (II) (III)

ii) :
. (III)

. (I) (IV)

. (IV)

. (III) (IV).

7. CH3-COOH, C6H5-OH, C3H7-OH CH3-CCH

NaHCO3:
. CH3-COOH C6H5-OH
. CH3-COOH
. CH3-COOH, C6H5-OH C3H7-OH
. .

117

8. C6H5COOH , C6H5OH , C6H5-CH2-OH

CH3-CCH
i) :
.
. C6H5COOH CH3-CCH
. C6H5COOH , C6H5OH C6H5-CH2-OH
. C6H5COOH
ii) NaOH:
.
. C6H5COOH
. C6H5COOH C6H5OH
. C6H5COOH , C6H5OH C6H5-CH2-OH.
9. HCOOH, CH3CH3, CH3CH2NH2
CH3COONa
i) HCl:
.
.
.
.
ii) HCl C3COOH:
.
.
.
. .
10. CH3-CH=CH2 (I), CH3CH(OH)CH3 (II),
CH3-CCH (III), CH3CH2CH2NH2 (IV) CH3-CC-CH3 (V):
i) :
. (III)
. (II) (III)
. (IV)
. (III) (V)
. (I) (III)
ii) :
. (III) (V)
. (IV)
. (II) (III)
. (I)
iii) :
. (IV) (V)
. (II)
. (II) (III)
. (IV).
11. C5H8,
CuCl :
.
.
.
. .

118

12.

i) :
. ()
. ()
. ()
. ()
ii) :
. ()
. ()
. ()
. () .
13. CH3COONa (I), CH3CCNa(II), CH3ONa (III)
NaCN (IV)
i) :
. (II) (IV)

. (II), (III) (IV)

. (I) (III)

ii)
:
. (II) (IV)

. (II), (III) (IV)

. (I) (III)

. .

H
|

14. : : O H (I), C H (II),

:
. (I) (II)

. (II) (III)

. (II) (IV)

. (I), (III) (IV).

119

N (III),

NH 3

(IV)

15.
:
CH3CH2Cl + CH3CCNa CH3CH2CCCH3 + NaCl
CH3CH2CH2Cl + CH3CH2ONa CH3CH2CH2OCH2CH3 + NaCl
:
-

. CH3CH2+ CH3CH2CH2+

. CH3CH2 CH3CH2CH2

. CH3CC+ CH3CH2O+

. CH3CC CH3CH2O

16. .
:
.
.
.
. .
17. Cl2 :
.
.
. C4H9Cl
. .
18. NaCCNa (I), CH3CCNa (II), CH3Cl (III)
CH3CH2Cl (IV) CH3CH2CCCH3 :
. (II) (III)

. (I) (IV)

. (II) (IV)

. (I) (III) (I) (IV).

19. Na
CH3CH2OH :
. CH3CH2ONa

. CH3CH2OH CH3CH2ONa

. NaOH CH3CH2OH

. CH3CH2ONa NaOH

120

20. C
-

1,5410 10m 1,3410 10m.

C
:
-

. 1,5410 10m
-

. 1,3910 10m
-

. 1,3410 10m
-

. 2,8810 10m
-

. 1,5410 10m 1,3410 10m.

21. C6H6, C2H4, C4H6 C6H5-CH=CH2
i) CCl4:
. C2H4 C6H5-CH=CH2
. C6H6, C2H4, C6H5-CH=CH2
. C2H4, C4H6 C6H5-CH=CH2
. .
ii) 12 :
. C6H6

. C2H4

. C4H6

. C6H5-CH=CH2.

22. :
. 1,2-

. 1,2-

. 1,1-

. .

23. HBr 1- :
.

. .

121

24. :
H 2 SO 4 , HgSO 4
CH3COCH3
CHC-CH3 + H2O

(I)

CHC-CH3 + 2HBr Br-CH 2 -CH -CH 3

(II)

Br
Cl
|

CHC-CH3 + 2Cl2 Cl- CH - C -CH 3

|

(III)

Cl Cl
Pd, Pt, Ni

CH3CH2CH3
CHC-CH3 + 2H2

(IV)

:
. (I)

. (II)

. (III)

. (IV).

25. CH3CH2MgCl
2--2-.
:
. CH3CH2CH=O

. CH3COCH3

. CH3CH=O

. CH3CH(OH)CH3.

26. Grignard
:
.
.
.
. , ,
Grignard .
27.
:
.

. Grignard

. Grignard.

122

28. :
. CH 3 CH CH 3

. CH3CH2CH2OH

OH
CH 3

CH 3

. CH 3 C CH 2 OH

. CH 3 C CH 3
|

OH

OH
29.
+

H+

(I)

+ 2

Ni

(II)

+ Grignard

H2 O

+ AgOH

(III)
(IV)

:
i) 2,-2,:
. (I), (II) (IV)

. (II), (III) (IV)

. (I), (III) (IV)

ii) :
. (I) (IV)

. (II) (IV)

. (II), (III) (IV)

30. HCl ,

:
+

. CH 3 CH 2 CH 2 CH 3 CH CH 2

. CH 3 CH 2 CH 2 CH 3 C CH 3

CH 3
+

CH 3

. CH 3 CHCH 3 CH 3 C CH 3

. CH 3 CHCH 3 CH 3 CH CH 2
|

CH 3

CH 3

123

31. C4H8O + H2 C4H9OH

:
.
.
.
. C4H10.
32. 2- :
. 1-
. 2-
. C4H8
. .
33. K2Cr2O7
:
.
.
.
. .
34. CH3CH=O + HCN CH3CH(OH)CN :
.

. .

35. , H2SO4- HgSO4,

Fehling.
:
.

. .

124

36.
-

CH3CH(CH3)COO .
:
CH3CH(CH3)CH2CH(OH)CH3

(I)

CH3CH(CH3)COCH3

(III)

CH3CH(CH3)CH(OH)CH3

(II)

CH3CH(CH3)CH(Cl)CH3 (IV)

:
. (I) (III)

. (I) (II) (III)

. (II) (III)

. (II) (III) (IV).

37.
( I)
( II).
i)
I :
. 3 - 2
. 3 H2SO4 - 3
. - 2
. 2 - 3
ii)
I II :
. -

. -

. -

. - .

38.
C4H8O
i) Tollens:
.
.
.
.
ii) :
.
.
.
. .

125

39. CH3-CH2-OH (I), CH3-CH(OH)-CH3 (II),

CH3-CH2-CH=O (III) CH3-CO-CH3 (IV)
i) H2SO4 KMnO4:
.
. (I), (II) (III)
. (I) (II)
. (III)
ii) Fehling:
. (III)
. (III) (IV)
. (I) (III)
.
iii) :
. (IV)
. (I), (II) (IV)
. (II) (IV)
. (I), (III) (IV).
40. CH3CCH (I), CH3CH2OH (II), CH3COCH3 (III),
CH3CH2CH=O (IV) CH3COOH (V)
i) 2 :
. (I) (V)
. (II), (IV) (V)
. (I), (II) (IV)
. (I), (II) (V)
ii) AgNO3
:
. (IV)
. (I) (IV)
. (IV) (V)
. (I), (IV) (V)
iii) 2 :
. (II)
. (II), (III) (IV)
. (II) (III)
. (IV).

41.
:
. ,
. ,
. NaOH Na2CO3

. CH3CH2OH
.

126

42. 0 - 10 C:
. .3 - .H2SO4 1,2,3-
.
. .3
. .3 - .H2SO4 1,3-.
43. :
.

. .

44. :
.
.
.
. .
45.
:
.

. .

46. :
.
.
.
-

. RCOO .
47. :
.
.
-

. Na RCOO

. (R-) (-COO Na ).

127

48.
i) :
. -SO3

. R
.
. R-.
ii) :
. -SO3

. R
.
. R-.
49. ()
:
. .3

. .2

. .3 - .H2SO4

. .2 - .H2SO4.

50. :
. , .H2SO4 NaOH
. , .H2SO4 NaOH
. , .3 , .H2SO4 NaOH
. .
51. :
.
.
.
. .

128

5.2.

1. (I)
(II)
, ( III).
(I)
(II)
(III)
.
. CH3Cl
.
. CH3CH3
1.
.
. CH3CH(Br)CH3
2.
.
. CH3CH2CH2MgCl
2. (II)
(I)
(III).
.
(I)
(II)
(III)
-

. Na

1. CH3CH2NH3+Cl

. NaOH

2. CH3CH2CH3

. NaHCO3

3. CH3COO Na+

. HCl

4. CH3CC Na+

. H2O

5. C6H5O Na+

3. (I)
(II) .
(I)
(II)
.
. CuCl
.
.
.
. NaOH
.
. HCl
.
. Na2CO3
.
. a

129

4.
(I)
(II).
.
(I)
(II)
. H-O:

. H3N:
. NC:

.
-

. C O:
|

. -CC:

. -COO:

.
.
.

5. (I)
(II) (III).
.
(I)
(II)
(III)
. CH3CH2CH(OH)CH3 . Ag2O 1.
. CH3CH(Cl)CH3
. CH3OH
2.

. CH3CONH2
. SOCl2
3. 2-
. HCOOH
. H2SO4 4.

6. (I)
(II) ,
(III).
(I)
(II)
(III)
.
. Br2 CCl4
1. C6H5Br
.
. Br2
2. C2H5Br
.
. Br2 FeBr3
3. C6H5NO2
. .3 .H2SO4
4. C2H4Br2
. HBr

130

7. (I)
(II)
(III). .
(I)

(II)

(III)

. CH3CH=CH2

. Br2 CCl4

1. 1,2-

. CH3CCH

. / H2SO4

2. 1,1-

. CH2=CH2

. / H2SO4 - HgSO4 3. 2-

. CHCH

. HBr

4.

8. Grignard (I)
(II)

(III). .
(I)

(II)

(III)

. CH3CH2MgCl

. HCH=O

1. 2--2-

. CH3MgCl

. CH3CH=O

2. 2-

. CH3CH(CH3)MgCl

. CH3COCH3

3. 1-

. CH3CH2CH2MgCl

. CH3CH2CH=O

4. 3--2-

9. (I)
(II)
(III). .
(I)

(II)

(III)

. CH3CH2CN . / H2SO4

1.

. CH3CH=O

. NaCN / H2SO4

2. 2,-2,

. CH3CN

. H2 i

3.

. CH3COCH3

. CH3MgCl / 2

4. 2--

131

10. (I)
(II)
(III).
.
(I)
(II)
(III)
. CH3CH2OH
. Tollens
1. CH3COONa
-

. CH3COCH3

. MnO4 /H+

2. CH3CH2COOH

. CH3CH2CH2OH

. I2/NaOH

3. CH3COOH4

. CH3CH=O

2-

. Cr2O4 /H

4. CH3CH=O

11. (II)
(I)
(III). .
(I)
(II)
(III)
.
.
1.
. 1-
.
2. PVC
. .
3.
.
.
4. 1-
.
.
5.
12. (II)
(I)
, (III).
(I)
(II)
(III)
. . CH3CH2OH
1.
.
. CH3COOH
2.
.
. CH3CH=O
3.
.
. CH2=CH2
4.
. CH3CH(OH)CN

132

13. (I)
.
(I) (II)
.
(I)
(II)
. CH3CH2Cl CH3CH2CN
. SOCl2
. CH3CCH CH3CCAg
. .HNO3 - .H2SO4
. CH3CH2OH CH3CH2Cl
. H2SO4
. CH3CONH2 CH3COOH
. Fehling
. C6H6 C6H5NO2
. NaCN + H2SO4
. CH3CH=O CH3CH(OH)CN
.
. CH3CH(Br)CH3 CH3CH=CH2
. NaCN
. CH3CH2CH2OH CH3CH2COOH
. AgNO3
-

. CH3CH2CH=O CH3CH2COO

. H2SO4 / KMnO4

14. (I) .
(I)
(II).
(I)
(II)
.
.
. 2-
.
.
.
. 2-
.
. 1-
.
15. (I)
(II) ,

(III).
(I)
(II)
(III)
. CH3CH(OH)CH3 . I2
1.
. CH3CCH
. AgNO3
2.
. CH3CH2CH=O . H2SO4
3.
. CH3CH=CH2
. H2SO4 / K2Cr2O7 4.
. Br2 CCl4
5.3.
133

1.
, .......................... ,
........................... ................................... .
..................................... C-A.
...........................................
............ ........... .
.........................................
................................................. ............................ ,

.................................... .............................. .
2. C-Cl , C-MgCl C-H
CH3CH(Cl)CH3, CH3CH2CH2MgCl CH3CH3
................................... , ................................
............................. ................................. ,
............................ .......................... .
3. CH3COOH, CH3CH2OH, C6H5OH CH3CCH
............................... .
:
) Na .........................................
) NaOH ....................................
) NaHCO3 .................................
4. CH3CH2MgCl, CHCNa CH3CH(CH3)ONa

................................... , ................................... ............................ .

.............................. , ............................. ...............................

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

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

........................................ .
5. R-NH2 .........................
........................ . ........................

134

 ........................................... . .. CH3CH2NH2
....................... ................................ .
6. ............................. .
......................................... . ..
-

CH3COO .................... ...................... .

7. CH3CH(Cl)CH3 CH3COONa
................................ ................. C
CH3CH(Cl)CH3 .............
...........................................
................................................... .
8. CH3CH(Cl)CH3 NaCN ............ ................ C CH3CH(Cl)CH3
..................
.............................. ................................................ .

..................................................................................................................... .
9. (ROH) ............... .. CH3CH2OH
Na ............................. .
................. ..
CH3CH(OH)CH3 ...................
.........................

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

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

........................... .
10. CH3COOH CH3CH(OH)CH3 ..................
CH3COOH ...........................
CH3CH(OH)CH3 ..................................

135

 ................................................... .
........................................ .............. ,
H+

................
......................................... .
FeCl3

11.

.

CH3CH2OH

SOCl2

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

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

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

CH3CCAg

CH3Cl

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

CH3CCCH3

C4H6

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

CuCl
.....................

CH3ONa

CH3CH2OCH3

12. :
H O

........................ + AgCl
) CH3CH2Cl + ......................

) CH3CH2Cl + ...................... CH3CH2CN + ..................

) CH3CH2Cl + ...................... CH3CH2CCCH2CH3 + ..................
) ................... + ...................... CH3CH2COOCH2CH3 + .................
) ................... + CH3Cl CH3OCH2CH3 + .................

13.
.
CH3COOH + CH3CH(OH)CH3

) ........................ + ...............
+

) CH3CH2CONH2 + ............. + H ........................... + NH4

136

) C6H6 + .................

......................... + HCl
C6H5NO2 + H2O

) .................... + .....................

14. Lewis
........................... .
.H

2SO
.................................. , ...................................... .
C
................. ................ .
15.
. C
C,
......... . ........................ ,
C ............................... . .......
C ......................
.......................... ........................
............................... ....... , ..................................
..................
................... ,
.
16. .................................
...................................... , ....................................
.
17. .......................... ........................ C6H6

C6H5NO2, ...................................... .
18. 2 ......................... ,
Br2 .................... , HCl 2 .................. .

137

 ..................................... , ................................................... ,
................................................. ........................................................... .
19. HCl CH2=CH2
............ ................................ + .......... .
, ..........
+, ..............................
.................... ...............................
........................................ .
20. 2 H2SO4 ,
......................................,
.................................... .
21. HCl ................
........................................... . 2
, ................................. ................................. ,
.............
............................. ....................................,
................................. . .........
............................
.............................. ,

.............................. .
22. , ,
..............................................
..................................... .
23. H2SO4 - HgSO4
.............................. , ............................... .

138

24. ........................

C .................................. .
25. Br2
....................... ,
......................................... .
26. ..............................
Grignard ...................................
2,-2,.
27. NaCN H2SO4
......................................... ,
H2SO4 ............................... .
28.
:
) CH3MgCl + ...................... .......................

CH 3 CH CH 3
|

OH
) CH3CH2MgCl + ........................ ........................... + g(OH)Cl

CH 3
|

CH 3 C CH 3

) CH3COCH3 + .................... ...................

+H2O

) ................ + ................ CH3CH2CH2MgCl- Mg(OH)Cl

OH
...................

29. CH3CH=O
HCN ........................... C
C .........................
.........................................
.
+H2O
- Mg(OH)Cl

30. C4H9Cl


+H2O
- Mg(OH)Cl

139

..................................... ................................. ,
....................................... .
31. 1- .H2SO4 170 C
................................. , ...............................
........................................... .
32. ............................ HCl 1-
................................... ,
................... ........................................... .
33. CH3CH2CH2OH 2Cr2O7 ...............................
................................, KMnO4
................................... .
34. C3H7OH 2Cr2O7
................................ ,
................................... .

.
........................................ .
35. ................................
I2
......................... . KMnO4
............................... NaHCO3
............... .
36. .............................
I2
......................... , ...........................................
Cu2O.
37. Orlon :
-CH2-CH(CN)-CH2-CH(CN)-CH2CH(CN)-.
........................ , ...............................

140

 .
........................
.........................
............ .
38.
( )

.
, .
............

Br2 CCl4

K2Cr2O7

Tollens

I2

CH3CH2OH
CH3CH=CH2
CH3CH(OH)CH3
CH3CH=O
CH3CCH
CH3COCH3

39.

, .

141

CH
CH..................
Cl2/FeCl3

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

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

H2SO4-HgSO4

C6H6
NaCCNa
CH2=CH2
........................
................
40.
- +

MnO

...............
............... HCl
..................
C6H
4 /H
5NO2
C6H5NH2
, .
CHCH

CH3CH2Cl

......................
CH3CH2OH

H2SO4

H2/Pd, Pt, Ni

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

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

CH3CH2OH
41.
...................
..................

..............
, .
CH2=CH2
CH3CH=O
CH3CH2ONa
............

CH3CH(OH)CN

/
H2SO4
....................

CH3Cl

HCl

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

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

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

CH3CH2CN
142

2/Pd, Pt, Ni

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

42.

,
X .

CH3CH=CH2

CH3CH(Cl)CH3

CH3CH(CH3)CN

CH3CH(CH3)CH2NH2

CH3CH(CH3)COOH

CH3CH=CH2
HBr

HCl

/ H2SO4

........................
.......................
......................
43.

Mg : Cr2O72-/H+
.............
CH3CH2CH=CH2
CH3CH2CH(OH)CH3
CH3CH2CH2CH2Cl

CH 3CH
-CHC2COONa
C-CH 3
3CH
|

........................
CH3CH2COOH.

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

CH 3

: ......................
, : ................... , :
...................... , : .....................
..............
NaCN, H2SO4
44.
.......................
.......................
:

H2O
/ H SO
2

CH3CH(CH3)CH(OH)CH3

143

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

: ...................... , : ................... , : ...................... , : .....................

45.
.............
............
COOH

.................
, CH
3CH
2
CH3CH2Cl
,
.................
...............
.............
CH3COOH
CH3CH2CH2OH

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

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

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

CH3CH(OH)CH3

46.
,
,
.
.............
..............
....................
.................
CH3CH2OH
...............

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

CH3CH(OH)COOH
.................

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

HCOOH

47.
,
, .

48.
.............
............
2NH2
.................
, CH
3CH

CH3CH2Cl
,.............
.................
. ..............
CH CH CH NH
3

144

49.
,
,
.
.............
............
..................
.................
CH3CH=CH2
..........

..........

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

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

..........

..........
CH3COOH

CH3CH(CH3)CH2NH2

...........

50. CH
....................
3CH=O
,
................. .
,
........
...........
................

............
.................
CHCH

.............
............
...............
CH3CH(OH)CH2CH3

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

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

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

...................
..................
CH3CH2OCH
2CH3

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

...........

CH3CH2COOH

............
.........................
51.
CH3COOCH2CH3
.............
,

, .
CH3CH2CH2CH2CH2CH3

145

52. ..............................................
.
.
............................. ......................
..........................................................
............................................. ,
................................................ .
53.
............................... ................. .................. ,
...................... .
.......................................
................................. .
54. ........................
.......................................... ........................ .
146

55. ...............................................
............................ .........................
.
56. .................... .................... ...................
................... . .................... ,
.................... ....................... .
57. -- NaOH
.................................... ..............
C15H31COONa, ................................. , ................................. .

147

58.
.............................. . ........................... .
.................................. ............................................

................................. .............................................
............................................................... .
-

59. -COO Na+

.........................................
.................. .................................
....................................... .................. .
60.
..................
....................... .............................. .
.................................................
...................... ...................... ....................
.
61. ,
.............................................. .
..................................... .................................

:
..........
...................... + .....................

.......................... + ............... .

62. ..............................
................................... ,
..................... ................
................... .

148

5.4 -
.
, .

1. .
2. C-Br CH3CH2Br
C 6
.
3.
C .
4. To
-

C-H CH3CH3 (CH3CH2 ).

5.
, , .
6. aOH
pH 5 - 7, -
CH3COOH, .
7. aOH
pH 5 - 7,
.
8. C4H6
CuCl .

149

9. CH3CC
-

CH3CC + 2 CH3CC + ,
.
10. :
-

RO + H2O ROH + OH ,
.
11. R-NH2
.
12. CH3CH2Cl 3
CH3CH2NH2.
13. 2 CH3CH2CH2Cl CH3CH2CH2OH,
CH3CH2CH2Cl + 2 CH3CH2CH2OH +
HCl.
14. CH3COOCH2CH3 CH3COONa
CH3CH2Cl, CH3CH2COONa CH3Cl.
15. KCN
C
.
16. CH3CH2Cl
CH3COONa .
17. CH3CH2Cl CH3ONa
.

150

18. g SOCl2 g ,
( + ) g.
19. , H2SO4,
100%.
20. H2SO4
-

: CH3CH2CONH2 + H2SO4 (CH3CH2CONH3+)2SO42 .

21. CH4
CH4.
22. 2 - ,
.
23. C
C .
24. .
25. HCl CH2=CH2
.
26. H2SO4,
.
27. .

151

28. H2SO4-HgSO4 .
29. Br2 CCl4,
.
30. HCl
1,1-.
31.
Grignard
.
32. C4H10O

Grignard .
33. HCN
.
34. H2SO4
.
35. 2,- .
36. 1- 2- 170 C
H2SO4, .
37.
C5H12O 170 C H2SO4, .

152

38.
.
39. K2Cr2O7
CH2+2O , ,
CH2O CH2O2.
40. K2Cr2O7
C4H10O ,
, C4H8O
C4H8O2.
41.
.
42. C4H10O
KMnO4
OH
|

CH 3 C - CH 3
|

CH 3

43. C4H8O
AgNO3
.
44. 1-
, KMnO4.
45. C4H10O
2
.

153

46. 1- 2-
,
KMnO4.
47. ,
.
48.

.
49. , .

50. NaOH .
51. .
52.
.
53.
.
54.
.
55.

.

154

5.5.

1.
C-A;
;
2. C-Cl 2,2,-
.
3.
C-A ;
.
4. C-Cl
C4H9Cl.
5. ;
C-H
.
6. ;

.
7.
: ) NaOH ) 3
.
8. C6H5-CH2-OH, C6H5-COOH, C6H5-CCH
C6H5-OH Na;
.
155

9.

(I). ;
10.
,
( )
.
11.
C3H7-NH2,
HCl
.
12.
Mg .
13.
) , ) .
14. ;


.
15.
.
16.
CH3CH2Cl + CH3ONa CH3CH2OCH3 + NaCl .

156

17. ;
,
.
18.
.
19.
Lewis, .
20. ;
.
21. HCl
;
.
22. :
) 1,2- ) 1,1--
.
23. ) )
) ; ;

157

24.
Grignard 2,-2,.
.
25.
) C
) C .
26.
) ) .
27.
2--
;
.
28.
2,-2-;
;
29.
2-
.
30. : ) KMnO4
) K2Cr2O7
;
.

158

31.
K2Cr2O7 .
,
.
32.

C3H8O.
33. Tollens; Tollens
.
34. Fehling;
Fehling .
35.
: ) )

) ) .
36. ;
37. C5H12O,
. .
38.
;
2000 ;

159

39. ;
;
40.
) )
.
41. ;

.
42. ;
43. ;
( C17H33COOH).
44. .


.
45.
.
46.
.
47.
.
;
160

48. ;
49. )
, ) ) ;

5.6.

1.

R
|

C-A R- C A .
|

R
.
, .
2.

.

.
3. CH3CH2CH2CCH, CH3CH2COOH,
C6H5OH CH3CH2CH2OH ) Na, ) NaOH, )
NaHCO3; .

CH3CH2CH2CCH .

161

4. 1, 2 3 1-,
1- .
)
.
)

. .
5.
R- ) R-OH, ) R-O-R,
) R-COO-R, ) R-CN ) R-CC-R.
;
6. )
:
CH3Cl + CH3CH2ONa CH3CH2OCH3 + NaCl
CH3Cl + Cl2 CH3Cl + HCl
) :
,
.
7. R-NH2 .
)
R-NH2 C3H9N.
)
i)
C ii)
C .

162

8. : ,
: .
.
9.
H2SO4,
: RCOOH + ROH

+ RCOOR + 2.

)
; ;
)
.
10.
.
;
11. Kekul
,
C6H4Br2.
) ;
)
;
)
Kekul.
12.
HCl , .
;

163

13. HCl
.
.
14. Br2 CCl4.

Br2/CCl4 CH3CH=CH2 CH3CCH.
) .
)
.
15. Grignard
:
) C
) C
) C .
16. CH3CH2CH(OH)CN;
.
17. : ) ) .
18. HCN ,
2-.

) 2- ) 2-2,- . ;

164

19.
C4H10O
.
-

. MnO4 /H+ Cr2O72 /H+

,
;
20. 1-,
2- 2,-2,.
)
,
.
)
.
21. CH2O
Tollens .
)
.
) Tollens.
)
.
22. 1 2 CH3CH2CH=O CH3COCH3.
)
1 2
.
)
.
23. , 2
, : ) , ) , ) ) .

165

24. ;
,
.
25. : NaCN, H2O, HgSO4,
H2SO4, .

2-- .
26. : Na, SOCl2, H2, 3,
H2SO4, Mg, Ni, H2O H2SO4 - HgSO4.

,
:
) CHCH CH3CH2OH CH3CH2CH2CH2CH2CH3
) C6H6
) CHCH CH3CH2OH CH3CH(OH)CH2CH3.
27. :
CH3CH2CH2CH=O
CH3(CH2)4CH3
CH3(CH2)3CCH
CH3CH=CHCOOH
CH3(CH2)3CH=CH2
CH3CH2CH2COOH.
,
:
i) Br2 CCl4, ii) Na2CO3 iii)
AgNO3.
28. :
CH3CH2CH(OH)CH3
CH3CH2COCH2C3
CH3CH2CH(OH)COOH
CH3CH2CH2COCH3.
CH3CH2CH2CH2CH=O
)
, : i) KMnO4
ii) I2/KOH iii) .
)
.

166

29.
.
) ;
.
) ;
30. RCOONa

.
31. .
.

.
32.
.

;
33. ;
.
34.
.
,
.

167

5.7. -

1. , CH3CH2OH,
CH3COOH Na2CO3.
)
CH3CH2OH,
.
)

.
.
2.
, :
) (CH3CH2ONa)
) 0,1mol 1L HCl 0,1M
) CH3COOH 0,1M NaOH 0,1M
) Na
.
3. 9,2g
4,6g Na.
,
.
) ,
.
) .
) STP .
: C:12, H: 1, O: 16, Na: 23.

168

4. 1mol ,
C, H 134,4L CO2 STP.
) C
.
) Na 0,1mol 1,12L H2 STP.
NaOH,
NaHCO3. (
) . .
5. 12g , C, H
Na 2,24L STP.
4,48L STP.
) ,
, Na.
) NaOH,
.
) STP
30g .
: C:12, H: 1, O: 16
20%v/v O2 80%v/v N2
6. ) ,
:
CH 3 CH CH 3 + 3

(I)

Cl
+ a + NaCl + H2O

(II)

+ CH3COOH

(III)

) (I)
.

169

7. 1 2 :
C, H
60
Na ,
NaHCO3 1.
) 1 2.
) STP , 1mol 1 2mol NaHCO3.
) 1 2
,
; .
: C: 12, H: 1, O: 16.
8.
T =

0,2mol
0,2mol .

CH3CCH

0,46g
.
) .
) .
)
.
,
.

. Na: 23.

170

9. i) ,
R .
) RBr + ..................... CH3CH2OCH2CH3 + NaBr
) RI + ...................... CH 3 C O CH 2 CH 3 + NaI
||

O
) RCl + ...................... CH3CH2CCCH2CH3 + NaCl
) RCl + ...................... CH3-CN + .................. .
ii)
. .
10. i)
:
) CH3CCCH2CH3

) CH3CH2OCH3 .
:
.
ii)
12g CH2CH2OCH3.
: C: 12, H: 1, O: 16, Br: 80.
11. 4mol CH3CH2I.
)
Ag2O, H2O Na
.
)
.
: C: 12, H: 1, O: 16.

171

12. 10,9g Ag2O.

4,6g.
) .
)
,
.
: C: 12, H: 1, O: 16, Br: 80.
13. Ag2O 2,18g

0,92g .
) .
) 1,8g CH3COOH

70mL NaOH 0,2M.
CH3COOH.
: C: 12, H: 1, O: 16, Cl: 35,5, Br: 80, I: 127.
14.
( ) CH3CH2OCH3.

( ) CH 3 C OCH 2 CH 3 .
||

) , ,
.
) :
129g


48g ,
.
: C: 12, H: 1, O: 16, Cl: 35,5.

172

15. )
:
+

CH 3 CH O C CH 3 + 2
|

||

CH 3

(I)

+ + 2
(II)
+ ................ + .................
(III)
)

(I).
,
20,4g
;
: C: 12, H: 1, O: 16.
16. CH 3 O C = O
|

.
0,2mol .


. .
: C: 12, H: 1, O: 16.
17. 500mL
HCl . HCl, .
)

.
)
HCl, 200mL
1,48g .
: C: 12, H: 1, O: 16, N: 14.

173

18. SOCl2 12g

8,96L STP.
) .
)

, Grignard .
)
.
19. 56L STP.
)
.
,

.
) ( STP) CO2
10L ( STP) .
,
.
20. g CH2=CH2 Br2 CCl4.
Br2 g CH3CH=CHCH3 g
CH3CH=CH2 g CH3CCH g CH3CCCH3.
) , , , .
)
2 Ni.
2 11,2L ( STP) .
.
: C: 12, H: 1.

174

21. H2SO4
.

5,4g 0,6g.
) ;
) STP
H2SO4;
)
,

.
22. 0,2mol H2SO4
0,2 mol ,
KMnO4 0,1
.
i) :
.
. 2-
.
. 1-.
,
.
ii) KMnO4
.
23. , 0,2mol CH3CH=CHCH3
H2SO4 mL
KMnO4 0,5, 0,2mol
CH3CH2CH=CH2 H2SO4
mL KMnO4 0,5.
i) .
ii)
:
) =
) >
) < < 2
) = 2.
.
24. CH3CH2OH CH3OH
.
175

 1
3,9g
H2SO4 (1) KMnO4 0,5M
.
KMnO4 ,
CH3OH CO2 :
5CH3OH + 6KMnO4 + 9H2SO4 3K2SO4 + 6MnSO4 + 5CO2 + 14H2O.
200mL 1.
2

I2 .

.
)
.
) STP 1 .
)
15,6g,
.
: C: 12, H: 1, O: 16, J: 127.

25.
.

+ 2/2SO4
+ H2/Ni

+ AgOH

+ H2O

CH3CH=O + CH3MgCl

176

) , ,
;
)
: i)

ii)

iii) .

( ).
)
11,4g
0,6g ,
;
: C: 12, H: 1, O: 16.
26. Grignard CH3MgCl , CH3CH2MgCl
CH3CH=O , CH3CH2CH=O.
) Grignard
,
.
.
)
197g CHI3
)
Grignard
CHCH H2/Ni, Mg/, SOCl2,
H2SO4 - HgSO4.
: C: 12, H: 1, O: 16, I: 127.

177

27. 1, 2 3 3,7g
, .
nO4 :
1 40mL nO4,
2 3
80mL nO4.
:
) , ,

) ,
.
) KMnO4 0,5,
, .
: C: 12, H: 1, O: 16.
28. CH3CH=CH2, CH3CCH, CH 3 CH CH 3 ,
|

OH
CH 3 C CH 3 , CH 3 CH CH 2 Br .
||

Br

) ,

.
.
)
:

CH 3
|

i) CH 3 CH 2 CH 2 CH CH 3 ii) CH 3 C COOH .
|

OH

CH 3

178

29. , ,
:

) , ,
CH2=CH2, CH3CH2OH, CH3CH=O CH3CH2Cl.

.
)

2-.
) g2O,

CH3CH2OH, CH3CH=O
CH3CH2Cl.
.
30. :
C

.
)

.
)
,
, ,;
.

179

31. ,
, ,
CH2=CH2
.

, .

,

.
)
.
)
.
32. , C4H8.
)
.
)
.
.
) .


.
) HCl .

,
. ,
.

180

33. 1, 2, 3 4
1-, 2-, ,
.
) :

1 4
I2/KOH
2 4 .

.

.
)
: I2/KOH.

.
34. 1-,
2-.
) : KMnO4
I2,

.
) : H2SO4 K2Cr2O7,

.

181

35. , C4H10O
:

KMnO4

2

H2SO4 170 C
,
.
)
, .
) CO2
37g , .
: C: 12, H: 1, O: 16.
36. 21,6g 1,2g H2
Ni.
Br2 CCl4 4% w/v 800mL .
)
C4H6.
) 0,2mol H2SO4HgSO4 ,
2
.

.
: C: 12, H: 1, I: 127, Br: 80.
.

182

37. :

Mg

/
H2SO4 - HgSO4

+ 2

I2/KOH

+ CH3CH2COOK

) , .

2/.
) , ,
.

, .
) 0,4mol 0,5mol
60%, mol
;
38. ) , , ,
:
+
H2SO4/170 C H2O/H

MnO4 /H+

HCN

.
/ H2SO4
CH 3
|

CH 3 - C - COOH
|

OH

)
- ,
.
) : 2/
,
.

.

183

39.
2,-2,-,
. Pt,
2,2,5--.
) , .
) ,
.
) (
) 2,2,-,
.
40. Mg ,
.
3,2,.
) , , .
) .
)

.
41. C3H8O.
) :
SOCl2
2/,
.
SOCl2
2/.
) H2SO4
, 21,6g
2,4g .
.
) ,
2,
.

184

42. C4H10O
:
Na
KMnO4/H2SO4
2/NaOH.
)

.
) KMnO4/H2SO4 0,5
KMnO4 3,7g .
: C: 12, H: 1, O: 16.
)
.
43. K2Cr2O7/H2SO4
C3H6O,
Fehling.
)
.
) , , 4g
2/ 19,7g .

2/.
) 9,5g
6g , .
, .
: C: 12, H: 1, O: 16, I: 127, Br: 80.

185

5.8.
1
:
: 15 ( )
:

: .................................................... : .........................................
: ........ ........ : ......................... : .....................

:
1. :
C-C
................
................................. , C-H
.................... ..................................... .
: 4

2. ,
; 1mol ;
: 6

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

186

3. :
CH3Cl + A-B CH3-B + A-Cl (A B)
i) :
. CH3

. CH3

. :CH3

. CH2Cl

ii) C-B :
.
.
.
. , -.
.
: 4

4. C-Cl :
-

. :CH3 Cl
-

. CH3+ Cl

. CH3 Cl+
. CH3 Cl

i) .
ii) .
: 2 + 4

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

187

2
: -

-
: 15 ( )
:

: .................................................... : .........................................
: ........ ......... : .......................... : ...................

:
1. .
) ,
.
: 3

.................................................................................................................
.................................................................................................................
.................................................................................................................
.................................................................................................................
.................................................................................................................
)
.
: 3

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

188

2.
1- .
,
.
: 6

......................................................................................................................
......................................................................................................................
......................................................................................................................
......................................................................................................................
......................................................................................................................
......................................................................................................................
......................................................................................................................
......................................................................................................................
......................................................................................................................
3.


.

, .
CH3COOH

C2H5OH

C6H5OH

CH3-CCH

Na
NaOH
Na2CO3
NH3
: 8

189

3
:

-
: 15 ( )
:

: .................................................... : .........................................
: ........ ......... : .......................... : ...................

:
1.
:
) Na 2-
................................................................................................................
) Na2CO3
................................................................................................................
) CuCl
................................................................................................................
: 23 = 6

2. : CH3-CCH (I), CH3CH2OH (II), CH3COOH (III),

C6H5-CH2-OH (IV) CH3-CC-CH3 (V), :
.
. (II), (III) (IV)
. (I), (II), (III) (IV)
. (I), (III) (V).
.
: 2

3. .

190

) C4H6
AgNO3 .
: 3

................................................................................................................
................................................................................................................
................................................................................................................
................................................................................................................
............................................................................................................... .
) CH3CH2NH3+ .
: 3

................................................................................................................
................................................................................................................
................................................................................................................
............................................................................................................... .
4. 0,2mol CHCH .
) .
) STP .
: 3 + 3 = 6

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

191

4
:
: 15 ( )
:

: .................................................... : .........................................
: ........ ......... : .......................... : ...................

:
1. ) :
CH3CH(Cl)CH3 + CH3COONa ....................... + .......................
CH3-CH3 + ....................... CH3CH2Cl + ..................................
)

.
..................................................................................................................
................................................................................................................ .
)
.
..................................................................................................................
) .
..................................................................................................................
: 24 = 8

2. CH3-CH2-Br CHCNa
...............................
........................ ..........................................
................................................. .
: 4

3.
H2SO4:
192

)
) .
: 4

4.
(I)
(II). .
(I)

(II)

. NC:
. H-O:

. CH3COO:
. CH3O:

. CH3CC:

. 2-
.

. .
: 4

193

5
:
: 15 ( )
:

: .................................................... : .........................................
: ........ ......... : .......................... : ...................

:
1. .
CH2=CH2 + HCl ..........................
................................................................... , ..................................
+ ..........
....................
CH2=CH2 ............................. .
.............. ..............................
C
.................. ...............
.
: 10

2.
- :
)
.................................................................................................................
)
.................................................................................................................
: 4

194

3. )
2-
Grignard.
: 3

...............................................................................................................
...............................................................................................................
...............................................................................................................
.............................................................................................................. .
)

. .
: 3

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

195

6
:
: 15 ( )
:

: .................................................... : .........................................
: ........ ......... : .......................... : ...................

:
1. ) CH3+ , (CH3)3C+ , CH3CH2+ ,
+

CH 3 CHCH 3 .
........................ , .......................... , ........................ , ......................... .
) .
: 3 + 3 = 6

..............................................................................................................
..............................................................................................................
..............................................................................................................
..............................................................................................................
..............................................................................................................
2. Grignard
:
. 3-
. 1-
. 3--2-
. 2,3--2-.
: 4

196

3. ) :
CH3CH=CHCH3 + HCl ......................
CH3COCH3 + HCN ...................
: 2

)
;
: 2

..................................................................................................................
................................................................................................................ .
4. .
) 0,5mol 1- HCl
0,5mol 2-.
: 3

.................................................................................................................
.................................................................................................................
.................................................................................................................
................................................................................................................ .
) g CH2=CH2
2
g CH3CCCH2CH3.
: C: 12, H:1.
: 3

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

197

7
: -

. .
.
: 15 ( )
:

: .................................................... : .........................................
: ........ ......... : .......................... : ...................

:
1. C3H6O:
) ........................................ ,

................................................................................................................ .
) Cl2 ............................. ,

............................................................................................................... .
: 3 + 3 = 6

2. 1- H2SO4 170 C
. H2SO4
, K2Cr2O7 H2SO4 .
.
: 6

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

198

3. C4H10O,
KMnO4
H2SO4.
) .
: 4

.................................................................................................................
.................................................................................................................
.................................................................................................................
.................................................................................................................
.................................................................................................................
.................................................................................................................
)
KMnO4.
: 4

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

199

8
: -

. .
: 15 ( )
:

: .................................................... : .........................................
: ........ ......... : .......................... : ...................

:
1.
.
) KMnO4 H2SO4.
) K2Cr2O7
H2SO4.
) ( CH2=O).
) Cl2 ( ) 2-.
: 24 = 8

) ..............................................................................................................
) ..............................................................................................................
) ..............................................................................................................
) ............................................................................................................ .

200

2. 100mL (CH3CH2OH)
20 KMnO4 H2SO4.
i) :
.

. .

.
: 3

ii) :
. CH3CH2OH CH3CH=O
. CH3CH2OH, CH3COOH CH3COOCH2CH3
. CH3COOH
. CH3COOH, CH3CH=O CH3CH2OH.
.
: 3

iii)
.
: 6

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

201

1
: - - -

: 45 ( )
:

: .................................................... : .........................................
: ........ ......... : .......................... : ...................
1

1. :
. 1-
. 2-
. 1- 2-
. 1- 2-.
.
: 1

2. :
.
.
.
. .
.
: 1

3. 1mol CH3CH2ONa 1L H2O :

.

. .

.
: 1

202

4. C4H10O
2 .............................................
................................................................. .
: 2
2

:
) .

: 2 + 2 = 4

)
2- .
: 4
3

0,5mol H2SO4,
.
H2SO4,
Br2
4,2g.
) ;

.
) %
H2SO4.
: C: 12, H: 1.
: 4 + 3

203

2
: - - -

: 45 ( )
:

: .................................................... : .........................................
: ........ ......... : .......................... : ...................

1. :
i) :
. CH3NH2

. CH3 NH4

. CH3NH3+Cl

. CH4NH2+Cl

ii) :
. CH3

. CH3+

. CH3

. CH3NH3+.

.
: 1 + 1 = 2

2. H C O CH 3 :
||

O
.
.
.
. .
.
: 1

204

3.
HCl ,
:
+

. CH 3 CH 2 CH 2

. CH 3 CH 2
+

. CH 3 CH CH 2
|

. CH 3 CHCH 3

. CH 3 C CH 3
|

CH 3

CH 3

.
: 1

4. (I)
(II).
.
(I)

(II)

A. 1-

. -

B. 2-

. 2--1-

. -

. .
: 2

- ...

- ...

- ...

- ...

- ... .

1.
:
)
)
) .
: 3

) ..................................................................................................................
) ..................................................................................................................
) ..................................................................................................................

205

2. .
)

.
: 2

) 2--2- 2--1 170 C H2SO4

.
: 2
3

C3H8O
K2Cr2O7 H2SO4.

.
30,6g,
0,4mol .
) ;
)
.
) mol .
: C: 12, H: 1, O: 16.
: 2 + 2 + 3 = 7

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

206