3

2001 -

 2001 -

 2001 -

 2001 -

.
.
. .
(CO) ,
(CO2) ( H2CO3) (. CaCO3,
Na2CO3) .
,
( SC)2.

18000000. A
.
.
.
VIA
Z=6. : K(2) L(4)
4 . 4

C .
.

. C . 4 4 C
.

.


C.
.

. C-H,C-X ( X: F, CI, Br, I), C-O,
C-N
C-C C

.
. 1
C .

|
4

 2001 -
.C:C. CC
. .
| |
H H
| |
H-C- C- H
| |
H H
. C 2
2
.
.
|
|
.C::C. C=C

H H
| |
HC=C H
. C 3 3

. C : : : C . - C C - H-CC-H
,

. .
|
|
C H , CX ( X: CI,Br, I, F)
|
|
.
C= ,
|

C =
|

 2001 -

C

) A C :
C
( ) CH3-CH3
C ( 2
) (3 )
.. CH2=CH-CH3, HCCH
)
. .
()
.


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

CH3-CH-CH2-CH3
|
CH3
CH3
|
CH3-C-CH3
|
CH3

2-

 2001 -

:

.


CH2 CH2

CH2 CH2

CH2

/
\
CH2 CH2

( N, O, S) .
.

/
\
CH2 CH2

( )
C .
.
CH2 CH2

CH2 CH2


.

 2001 -

:

.
.
CH2 CH2

CH2 CH2

CH2
/
\
CH2 CH2

 2001 -

()

OMA
|
--C-OH
|

|
|
--COC

|
|
( T

C )

|
C=O
|

--CH=O
|
|
--CCC
| || |
O

--COOH -C OH
||
O

( )

( C=O

C)

( )

 2001 -
|
|
--COC --COOC-||
|
|
O

- ( X: F,CI,Br , I )
-- ---CN --CN

-- NH2 --NH
|
H
--NH2
--NH---N
|

( )

-----

.




( ) .
(
)
( )
(CH2) .

CH3CH3 CH3CH2CH3

10

 2001 -

C 2+2 H.
C2+2 H C 2+1
R H H R
R
.

CH4 H CH3
()
()

C2H6 CH3 CH3

( )

(:

C , , S)

H CH3 CH2
( )

()
CH3CH2CH3 H CH3CH2CH2 ()
CH3CH2CH3 H CH3CH
(
|
)
CH3
()
CH3CH2CH2 CH3 H CH3CH2CH2 CH2
( )

11

 2001 -
()
CH3CH2CH2 CH3 H CH3CH2CH
|
CH3
( )
CH3CHCH3 H CH3CHCH2
|
|
CH3
CH3
()
()
CH3
|
CH3CHCH3 H CH3C
|
|
CH3
CH3
()

( )

1.

.
CvH2v+2

=1

=2

v1 RH R C2+1 ( )

CvH2v+2 CH4

CvH2v+2

H
|
HCH
|
H

()

H H
| |
C2H6 CH3CH3 CCH
| |
H H
()

12

 2001 -
2.
.
CvH2v v2

| |
=2 CvH2v C2H4 CH2 =CH2 C = C ()
| |

3.
CvH2v-2 v2
=2 CvH2v-2 C2H2 HCCH H CCH ()

4. 2

CvH2v-2
v3
=3

CvH2v-2 C3H4 CH2=C=CH2 ( )

5.K
CvH2v+1OH v1 CvH2v+2O ROH R = ( CvH2v+1 )
=1
=1

CH3-OH
CH3-CH2-OH

6.K
CvH2v+1OC2+1
v1
1

CkH2k+2O k2

R-O-R ( ) R-O-R`( )

=2 C2H6O CH3-O-CH3

13

 2001 -

7. K
CvH2vO v1

Ck H2k+1-C-H k O
||
O
=1 CH2O HCHO -C=O
|
H

RCHO

8. K
CvH2v+1CC2+1
||
O
v1
1

CkH2kO k3

R-C-R ( )
||

R-C-R`( )
||

=3 C3H6O

CH3-C-CH3 ()
||

O

.
9. K
CvH2v+1-C-OH v O Ck H2k O2 k1
||
O
=

R-C-OH R-COOH
||
O

H-C-OH HCOOH
||
O

14

 2001 -

=1

CH3-C-OH CH3COOH
||
O

10.

CvH2v+1-C-O-C2+1
||

v
1

CkH2kO2 k2 R-C-O-R RCOOR`

||
O

=2 C2H4O2 HCOOCH3 H-C-O-CH3

||
O
11. A
CvH2v+1X v 1

R-X = ( F, CI, Br, I)

=1 CH3-CI

( I.U.P.A.C)

( ) (
).
.


.
()

. .
15

 2001 -

. C
.
1
C
-

. (
).

- 1
2
1

-----

.
.
-
. -
. -
. -
- ( - )

1. CH3-CH2-CH3
--
( 3 C -)
2. CH3-OH

--
( 1 C - )

3. CH3-CH2-CH=O

--
( 3 C )

4. CH3-C-CH3
||
O

--
( 3 C- )

16

 2001 -

5. CH3-COOH

-- (-- )
( 2 C- )

6. CH3-CH2-CH2-COOH -- (-- )
( 4 C )
7. CH3-C-CH2-CH3
||
O

--
( 4 C -)

8. CH2=CH-CH3
--
( 3 C 1 )
9. CHC-CH3
--
( 3 C 1 - )

.
.. CH3-CH2-CH2-CH3

.
C
( ).



.
,
.


.

17

 2001 -

3 4
5 6
CH3-CH-CH2-CH2-CH3
|
2 CH2
|
1 CH3
3--

CH3
1 2| 3
4
CH3-C-CH2-CH3
|
CH3

2,2 -

CH3-CH2-CH2-CH-CH3
|
CH3
2-

CH3
C2H5
1
2| 3
4 5| 6
7
CH3-C-CH2-CH-C-CH2-CH3
|
| |
CH3 C2H5 CH3
4,5--2,2,5--

18

 2001 -

C ,
,
C
.

. 3,5--4--2,5,7--
.
8 C-C-C-C-C-C-C-C

.
1

7 8

C-C-C-C-C-C-C-C

C2H5 C3H7 CH3
1

3|

4|

5|

C C C - C - C - C - C -C
|
|
|
CH3

C2H5

CH3

C2H5

C3H7

CH3

3|

4|

5|

C3 C C - C - C - C2 - C - C3
|
|
|
CH3

C2H5

CH3

19

 2001 -

.
4

CH3-CH-CH2-CH3

CH2=CH- CH - CH2
|
|
CH2

|
2CH
||
1 CH2

OH

|
CH3

H
.
6

CH3-CH2-CH2-CH-CH3
|
2CH2
|
1 CH3
H C .

.

.


C .
,
.
1

CH2=CH-CH=CH-CH3

1,3-

20

 2001 -
CH3
3| 4
5
6
CH3-C-CH2-CH-CH3
|
|
2 CH
CH3
||
1CH2
4

3,3,5--1-

CH2 = C C = CH2
| |

2,3--1,3-

CH2 CH2

| |
CH3 CH3
1

CH3-C=CH-CH3
|
CH3

2- -2-

CH2= CH C CH

1--3-

.
C
C
.

21

 2001 -

.
.



,

.
.
> >

CH3-CH-CH2-C=CH2
|
|
OH
CH2
|
CH3

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

CH3
6
5
4
3
|2 1
CH3-CH2-CH-CH2-C-CH3
|
|
CH3
CH3
T
.( >
> )
.
C ,
C
.
5

2 1

CH3-CH-CH=C-CH2-OH
|
|
CH3
CH3
4

2,4--2--1-

CH2=CH-CH2-COOH

3-
22

 2001 -

( -CH=O) , (-COOH)
( -CN) ,
( ) .
1
.
.
( )
.
1

CH3-CH-CH-CH2-CH3
| |
CH3 OH
5

CH2=CH-CH-C=CH2
| |
OH CH3
5

3 2

2--3-

2--1,4--3-

CH3-CH2-C-CH-CH3
|| |
O CH3

2--3-

.,
.
CH3-C-CH3
||
O

( 2-)

CH3
|
CH3-C-CCH ( 3,3--1-)
|
CH3
23

 2001 -

CH3
|
CH3-C-CH2-OH - ( 2,2--1-)
|
CH3

.

.
.( , , ).
OH OH
7
6
5 4| 3|
2
1
CH3 CH = C - C- CH - C= CH2
| |
|
C2H5 CH3
CH3
5--2,4--1,5--3,4-
.

,
.

-COOH > -COOR > -CN > -CH=O > -C=O > -OH >-NH2>
> -X ( ) > -2
|

> > > >

> > > > >

24

 2001 -

-CN
-CH=O
-C=O
|

- - (-)
- -

-OH

-NH2
- CI,Br,I
--2
-COOH

-, -, -,
CH3 CH3

|5 |4 3
2
1
CH3 - CH2 - C C CH - CH2 - COOH
|
| |
7

C2H5 CH3 OH

5--4,4,5--3-

3 2

CH2-CH2-CH=CH-CH2-C-CH2-COOH
|
||
OH
O
3--8-- 5-
CH3
5
4
|3 2
1
CH3 - CH - C - CH - CH = O
|
|
|
CI CH3 CH3
2,3,3--4--

25

 2001 -

CH3-CH-COOH
|
OH

2-

( )
-CH3-O-CH2-CH3

CH3-O-CH3

CH3-CH-O-CH-CH3
|
|
CH3 CH3

CH3CH2-O-CH-CH3
|
CH3

. C
( -O-R ) .

26

 2001 -

CH3-O-CH-CH3
|
3 CH3
2

2-

CH3-CH2-O-CH-CH3
3|
CH3
CH3-CH2-O-CH3

2-

(1)

CH3-O-CH3

.
RCOOH + ROH

RCOO R + H2O

H .
:

(-)
CH3COOCH3

( )

HCOOCHCH3
|
CH3
()
COOCH3
|
COOCH3

( )
27

 2001 -

CH3CH2COOCH2-CH-CH3
|
CH3

ONOMATO
( -R )
CH3CH2CN
CH3CH2CH2CN

( )
( )
O

.
CH3CH2-NH2

()

CH3-NH-CH3

()

CH3-N-CH2-CH3
|
CH3

()

ONOMATO
()


(CI,Br,I,F).
( ).

, .
CH3-CH-CH3 2--
|
Br

28

 2001 -
CH3-CH2-CI

CH2-CH2
| |
CI CI

1,2-

CH2=CH-CH-CH3
|
CI

3--1-

1. .
CH3COCH3
CH3CH2CH3
CH3CH2CH2CH3
CH3CH=CH2
CH3-CH-CH2-CH3
CH3-CH=CH-CH2-CH3
|
CH2=CH-CH2-CH=CH2
CH3
CH2CI-CH2-CH2CH2Br
CH3CH2OH
HCC-CH2-CH2-CH3
CH3-CH2-CH=O
CH3-CH2-CH2-COOH
HC-CH2-CH2-CH3
CH3-CH2-CH-CH3
||
|
O
OH
CH3CH2CC-CH3
CH3CH2CH2CCH3
HCCCH2COOH
||
CH2=CH-CH2-CCH
O
CH2=CHCH2-C-CH3
CH2=CH-CH-CH3
||
|
O
OH
CH3-CH-CH2-CH2-CH-CH3
CH2=CH-CH=O
|
|
CH3
CH3
CH3
|
CH3-CH-CH-CH3
CH3-C-CH2-CH2
|
|
|
|
C2H5 CH3
CH3
C2H5

29

 2001 -

(
) ()
. (
)
.

. O
.
. CH3-CH2-CH2-CH3 ( )
CH3-CH-CH3 ( )
|
CH3
.
.
. CH3-CH2-CH2OH
1-
CH3-CH-CH3
2-
|
OH

CH3-CH2-CH=CH2 1-
CH3-CH=CH-CH3 2-
.
.
.

CvH2v-2

30

 2001 -
.

C3H4

CH3-CCH
CH2=C=CH2

CvH2v+2O
. C2H6O

CH3-CH2-OH
CH3-O-CH3

CvH2vO
. C3H6O

CH3CH2CH=O
CH3-C-CH3

||
O

CvH2vO2
.

C2H4O2

CH3COOH
COOCH3

.

.
.
C ( ).
C
.
C
( C2H5 CH2-CH3 CH3)
.

31

 2001 -

. C7H16 .

CvH2v+2
.
CH3-CH2-CH2-CH2-CH2-CH2-CH3
CH3-CH-CH2-CH2-CH2-CH3
|
CH3
CH3-CH2-CH-CH2-CH2-CH3
|
CH3
CH3-CH2-CH-CH2-CH3
|
CH2
|
CH3
CH3
|
CH3-C-CH2-CH2-CH3
|
CH3

2--

3- -

3- -

2,2--

CH3-CH-CH-CH2-CH3
|
|
CH3 CH3

2,3--

CH3-CH-CH2-CH-CH3
|
|
CH3
CH3

2,4--

32

 2001 -

CH3
|
CH3-CH2- C-CH2-CH3
|
CH3

CH3
|
CH3-C- CH-CH3
| |
CH3 CH3

3,3--

2,2,3--

.
. C6H10
.
CvH2v-2.
. .
.
. .
CHC-CH2-CH2-CH2-CH3

1-

CH3-CC-CH2-CH2-CH3

2-

CH3-CH2-CC-CH2-CH3

3-

33

 2001 -

CH3-CH-CC-CH3
|
CH3

4--2-

CH3-CH-CH2-CCH
|
CH3

4--1-

CHC-CH-CH2-CH3
|
CH3

3--1-

CH3
|
CH3- C- CCH
|
CH3

.
CH2=C=CH-CH2-CH2-CH3

1,2-

CH2=CH-CH=CH-CH2-CH3

1,3-

CH2=CH-CH2-CH=CH-CH3

1,4-

CH2=CH-CH2-CH2-CH=CH2

1,5-

CH3-CH=C=CH-CH2-CH3

2,3-

CH3-CH=CH-CH=CH-CH3

2,4 -

CH2=C-CH=CH-CH3
|
CH3

2--1,3-

CH3-C=C=CH-CH3
|
CH3

2--2,3-

34

 2001 -

CH2=C-CH2-CH=CH2
|
CH3

2--1,4-

CH3-C=CH-CH=CH2
|
CH3

4--1,3-

CH3-CH-CH=C=CH2
|
CH3

4--1,2 -

CH2=C=C-CH2-CH3
|
CH3

3--1,2-

CH2=CH-C=CH-CH3
|
CH3

3--1,3-

CH2=CH-CH-CH=CH2
|
CH3

3--1,4-

CH2=C-CH=CH2
|
CH2
|
CH3
CH2=C-C=CH2
| |
CH3 CH3

2--1,3-

2,3--1,3-

35

 2001 -

.


CI, Br, -OH.

2
.
.




.
. C4H9CI

C4H10
CI .
CI.
CH3-CH2-CH2-CH2-CI

1--

CH3-CH2-CH-CH3
|
C

2--

CH3-CH-CH2-CI
|
C3

-1--

36

 2001 -

CI
|
CH3-C-CH3
|
CH3

-2--

. C4H7Br

C4H8 Br.

Br.
C-C-C-C

C=C-C-C
Br-CH=CH-CH2-CH3
CH2=C-CH2-CH3
|
Br

1--1-
2--1-

CH2=CH-CH-CH3
|
Br

3--1-

CH2=CH-CH2-CH2-Br

4--1-

C-C-C-C

C-C=C-C
Br-CH2-CH=CH-CH3

1--2-

37

 2001 -

CH3-C=CH-CH3
|
Br

2--2-

C-C-C C=C-C
|
|
C
C
CHBr=C-CH3
|
CH3

1---

CH2=C-CH2-Br
|
CH3

3---

. C4H7OH.

C4H8 .


.
C
C .
.
C-C-C-C C=C-C-C
CH2=CH-CH-CH3
|
OH
CH2=CH-CH2-CH2-OH

3--2-

3--1-

C-C-C-C C-C=C-C-C
OH-CH2-CH=CH-CH3

2--1-

38

 2001 -

C-C-C C=C-C
|
|
C
C
CH2=C-CH2-OH -2--1-
|
CH3
. C3H6Br2

C3H8 2 Br.
C.
Br.
CH3-CH2-CH-Br
|
Br

1,1--

CH3-CH-CH2-Br
|
Br

1,2--

Br-CH2-CH2-CH2-Br

1,3 -

Br
|
CH3-C-CH3
|
Br

2,2--

-


(-CH=O) C
(-C-C-C- ) C.
||
O
39

 2001 -
. C5H10O.

CvH2vO
. .
.
CH3-CH2-CH2-CH2-CH=O
CH3-CH2-CH-CH=O
|
CH3
CH3-CH-CH2-CH=O
|
CH3
CH3
|
CH3-C-CH=O
|
CH3

2--

3--

2,2-- ( )

.
CH3-CH2-CH2-C-CH3
||
O
CH3-CH2-C-CH2-CH3
||
O
CH3-CH-C-CH3
| ||
CH3 O

2-

3-
- ( 3--2-)

C ( R-O-R)
C .
. 2 C - (R-O-R),
40

 2001 -


.
.
C4H10O.

C4H10O CvH2v+2O

.
. .
C-C-C-C
CH3-CH2-CH2-CH2-OH 1-
CH3-CH2-CH-CH3
|
OH

2-

C-C-C
|
C
OH
|
CH3-C-CH3
|
CH3

-2-

CH3-CH-CH2-OH
|
CH3

-1-

.
CH3-O-CH2-CH2-CH3 ( 1-)

41

 2001 -

CH3-O-CH-CH3
|
CH3

( 2-)

CH3-CH2-O-CH2-CH3

( )

-

( -COOH)
C.
C ( -COOR)
. .
2 C .
1 C
,
.
. C5H10O2

CvH2vO2.
. .
.
CH3-CH2-CH2-CH2-COOH
CH3-CH2-CH-COOH
|
CH3
CH3-CH-CH2-COOH
|
CH3

2--

3--

42

 2001 -
CH3
|
CH3-C-COOH
|
CH3

(2,2-- )

.
H-COO-CH2-CH2-CH2-CH3

H-COO-CH2-CH-CH3
|
CH3

H-COO-CH-CH2-CH3
|
CH3

CH3
|
H-COO-C-CH3
|
CH3
CH3-COO-CH2-CH2-CH3
CH3-COO-CH-CH3
|
CH3
CH3-CH2-COO-CH2-CH3
CH3-CH2-CH2-COO-CH3

CH3-CH-COO-CH3 2--
|

CH3

43

 2001 -

CvH2v+3N
( R-NH2) , ( R-NH-R`)
(R-N-R`)
|
R``

NH2.

C .
.
. C4H11N.

CvH2v+3N.
.
. .
CH3-CH2-CH2-CH2-NH2
CH3-CH2-CH-NH2
|
CH3
CH3-CH-CH2-NH2
|
CH3
CH3
|
CH3-C-NH2
|
CH3

.
CH3-NH-CH2-CH2-CH3

44

 2001 -
CH3-NH-CH-CH3

|
CH3
CH3-CH2-NH-CH2-CH3
.
CH3-N-CH2-CH3
|
CH3

.

.

) O2
. C2H4 + 32 2CO2 + 2H2O

.
O2 ,
.

.

) .
20% 2 80% N2 v/v.
O2 . N2
.
O2
2.

45

 2001 -

20% v/v 2 80% v /v 2 .

100 L 20 L O2 80 L N2.


.

, , .
VN2 /VO2= 80/20

VN2=4VO2

VO2/V= 20 /100

VO2=1/5 V

VN2/V=80/100

VN2=4/5V

mol

mol 2 2 .
nO2 / nN2 = VO2/VN2=20 / 80 nO2 /nN2=1/4

) H CuO.
CuO .
CuO
.
.

C2H4 + 6CuO 2CO2 + 2H2O + 6Cu

O .
,
g .
CuO
CuO
m ( )=mCuO mCu=mO .

46

 2001 -

.
C CO2
.
C4H8 + O2 4CO2 + H2O

2 .
C4H8 + O2 4CO2 + 4H2

2 .
C4H8 + 6O24CO2 +4H2O


.
2.

. K
CvH2v+2 + (3v+1) O2 VCO2 + ( v+ 1) H2O
2
CvH2v+2 + (3v+1) CuO VCO2 + (v+1) H2O + (3v+1) Cu
B. K
CvH2v + 3v O2 v CO2 + v H2O
2
CvH2v + 3v CuO vCO2 + vH2O + 3v Cu
. K -
CvH2v - 2 + (3v-1) O2 vCO2 + (v-1) H2O
2
CvH2v - 2 + (3v-1) CuO vCO2 + (v-1) H2O + (3v-1) CuO
. K
CxH + (4+ ) O2 CO2 + 2
4
2
47

 2001 -

CxH + (4+ ) CuO CO2 + 2 + (4 + ) Cu

2
2
2
E. ( )
CvH2v + 2O + 3v O2 vCO2 + (v+1) H2O
2
CvH2v + 2O + 3v CuO vCO2 + (v+1) H2O + 3v Cu
Z. ( )
CvH2vO + (3v-1) O2 vCO2 + vH2O
2
CvH2vO + (3v-1) CuO vCO2 + vH2O + (3v-1) Cu
H. ( )
CvH2vO2 + (3v-2) O2 v CO2 + V H2O
2
CvH2vO2 + 3v-2 CuO v CO2 + VH2O + (3v-2) Cu
.
CxHz + (4x + -2z) O2 xCO2 + 2
2
2

() CO2, (2) , 2
( ) 2 ( )

. Y.
2 ().


V = VH2O
H

48

 2001 -
2. H2SO4,
CaCI2, ZnCI2, P2O5, Mg(CIO4) 2 , CuSO4

2 .
V = VH2O

m =mH2O

. CO2
To CO2 ,
, Ca(OH)2 ( Na2CO3, K2CO3).

2NaOH + CO2 Na2CO3 + H2O
Ca(OH)2 + CO2 CaCO3 + H2O

CO2 .
CO2
.
V = VCO2

m =mCO2
. CaCO3

CO2 .

. 2
H 2
.
2 (
2)
2
Cu, P(),
.
49

 2001 -

. 2
VO2 () = VO2 () VO2 ()

. (2)
.

. 2.
2 .
2 .
2, CO2 2
2 .
.

V=V V

V= V V 2

V=V2
2
2 :
% 2= 2 . 100
2
2 :
% 2 = 2 . 100
2

50

 2001 -

1. ;
CH3-C-H
||
O

CH3-C-CH3
||
O

CH3-CH2-CH2-CH-CH3
|
CH3
CH3-C N

CH3-CCH

CH3-C-OH
||
O
CH3-CH2-CH3

CH2=CH2

CH3-CH2-OH

H-C-O-CH2-CH3
||
O

2. N
.




3.
C3H8, C5H10, C3H4, C4H8O2, C2H6O, C4H8O, CH2O2
4.N .
CH3-CH2-CH2-CH2-CH3
CH3-CH2-CH=CH-CH3
CH3-CH2-CCH
CH3-C-CH2CH2CH2CH3
||
O
CH3-CH2-CH-CH2-CH3
|
OH

51

 2001 -
CH2-CH-CH2-CH-CH3
|
|
|
CH3 CH3
CH3
(CH3)2C=CH-CH3
CH3-CH2-CH-C=CH2
| |
CH3 CH3
CH3-C-CH2-CH3
|
C2H5
CH2=CH-CH-COOH
|
CH3
5. N o
C4H6 .

()
1)
;
Br
.
CvH2V v>1
1 ..

.
. H2SO4

52

 2001 -

2) N .
CH3-CH=C-CH3 + HCI ...............................
|
CH3
CH2=CH2 + CI2 ................................
CH3-CH=CH2 + ............................ CH3-CH-CH3
|
OH
CH3-CH=CH-CH3 + r2 ..................................

CH3-CH2-CH=CH-CH3 + H2 .....................................

. . ..

+ .. CH2-CHCH2
| |
CI CI

CH3-CH2-CH2-Br + KOH

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

3) CH3CH2CH2OH . H2SO4 170C ;

(
).
4) HCI ;

5) CI2
.

6) N .
2-
-

53

 2001 -
. H2SO4
7)
( ) ;
8)


1-
9) .
2

2 2-
CI
10) ;
11)
2 i

CN

Fe 500C
2-
CI2 .
CI .
12) ;

13) ;
.

14) ; N

54

 2001 -

15) .
16) . = 56.
.


1) 2
2) r2
3) HCI
'
1
.
1. C2-2 ( 3) :
)
)
)
)
2. :
) CH4
) C2H4
) C2H6
) C3H6
3.
)
)
)
)
( 9)
.
1. ) ) )
2. ;
( 6)
. .
)
) 2,3--
55

 2001 -
) 2-
) 2- -
)

( 10)

2
.
CH3-CH2-CH=CH2
CH2=CH-CH-CH3
|
OH
CH3-O-CH2-CH3
CH3-CH2-CH-COOH
|
CH3
CH3-CH2-COO-CH3

( 10)

B.N .
) C5H8
) C5H10
) C4H8O2

( 15)

3
,
.
CH2-CH2-CH2-CH3 + NaOH
|
CI
CH3-CH2-CCH + 2H2
CH3-CH=CH2 + Br2
CH3-CH2-CH-CH2 + 2KOH
|
|
CI CI
HCCH +HCCH
CH3-CH2-CCH +H2O
CH3-CH=CH2 + H2O
HCCH + HCN
vCH2=CH-CH3
CH3-CH2-CHO + H2

( 25)

56

 2001 -

4
. 1,2 g
2,64 g CO2.
)N .
) .
) .
.
( 15)
. 9,2 g .
) STP
.
) ;
.
( 10)

1. 6 g CH4 C3H8
. 10,8 g.
.
2. C2H4 C2H2 700 mL ( 20% O2 ,
80%2 v/v). .
CO2 100ml. % v/v
.
.
3. 7 g 5,6L STP.


56000.

.

70 Kg ;

57

 2001 -

1.
1- , 2- -2- .
.
2.
:
)
)
) 2- )
3. r = 60.
) N .
) N
.
4.11,2 L STP
. .
STP.
5. 4,48 L STP HCI.
AgOH 12 g
. ;
6. 750 mL 10% w/v.

11,2 L STP.
)
;
) ;
7 . 23 g .
Na .
) STP;
)T

Mr=88.

58

 2001 -
; 80%
.
8. 27,6 g 36 g H2SO4
.
35,2 g. %
;

,
-C.

:
1. (-C),
, .
CH3COOH ( - )
COOH
|
COOH

( - )

2. ,
( -), ( -),
( -2), ..
CH3CHCH2COOH
|
OH

CH3CH2CHCH2CH2COOH
|
CI

CH3CHCOOH
|
NH2

4.1.
,
, (COOH).

59

 2001 -
C2+1 COOH RCOOH.
:
HCOOH
CH3COOH
CH3CH2COOH
Bo CH3CH2CH2COOH
CH3CHCOOH
|
CH3

1. (RCH2OH) ( RCH=O)
.
RCH2OH + |O| RC= + H2O
RCH=O + |O| RCOOH

CH3CH2CH2OH + |O| CH3CH2CH=O + H2O

CH3CH2CH=O +|O| CH3CH2COOH

CH3CH2CH2OH +2|O| CH3CH2CO + H2O
2. (RCN)
.
H+

RCN + 2H2O RCOOH + NH3

OH-

60

 2001 -

H+

CH3CH2CN +2H2

CH3CH2COOH

NH3

OH-

3. .

RCOOR` + H2O
RCOOH + R`OH
H+

CH3CH2CH2CH2COOCH2CH3 + H2O CH3CH2CH2CH2COOH + CH3CH2OH

CH3COOH
.
, ,
.

- CH3COOH

.
CH3CH2OH +|O| CH3CH=O + |O|CH3COOH
-H2O

:
1. ,
, 5-10%.

(.. ) .

61

 2001 -
,
.
CH3CH2OH +O2 CH3COOH + H2O

H .

2. , . (
) .
, ,

C4H10 + O2 CH3COOH +

3. ( ) (
CH3CH=O)
CH3CH=O + O2 CH3COOH
H
(
) .
4. CO
( Rh)
CH3OH + CO CH3COOH

, .
17 C, ,
( Glacial) .
, , ,
. , ,
, .

62

 2001 -


1. .
(+).
CH3COOH CH3COO- + H+
, . (
+):
)

) ()
CH3COOH +NaOH CH3COONa +H2O
2CH3COOH +CaO (CH3COO)2Ca +H2O

)
(2).
2CH3COOH +Zn (CH3COO)2Zn +H2

) CO2
2CH3COOH +Na2CO3 2CH3COONa + CO2 + H2O
CH3COOH +NaHCO3 CH3COONa +CO2 + H2O

CO2

COOH .
.
) (-) 2

2.
63

 2001 -
(.. ) .
CH3COOH + CH3CH2
CH3COOCH2CH3 +
H2O

, , ,
.

,
, , , .
,

.

O 2--

() .

.
, , .

1. (..
) ,
.

C6H12O6

2CH3CHCOOH
|
OH

2. HCN
.

64

 2001 -

C3CH=O +HCN CH3CHCN + 2H2O CH3CHCOOH +NH3
|
|
OH
OH

, ,
.
, .
,
(-COOH), , (-OH)
. ,
.
CH3CHCOOH +|O| CH3CCOOH +H2O
|
||
OH
O

, ,
.
.

.
,
.

1. 18,4 g .
NaOH O,5 . :
) ,

65

 2001 -
) NaOH .
2. 2,3 L 100 (10 % v/v) .
50%,
.
=0,8 g/mL.
3. 6,1 g ( C6H5COOH )
0,25 . :
) ,
) .
4. Mr = 88.
) ,
) 17,6 g Na2CO3.
, STP.
5. CH3COOH 1,5 % w/v.
) NaOH 0,5
200 mL ;
) 400 mL Na2CO3.
, STP.
6. C3H6O2.
) .
) NaHCO3 .
.
)
:
Cv2v + H2O
()

H+

Mr = 116.
) , ;
i) Na .
ii) .
iii) KMnO4.

66

 2001 -

1. N
CH3COOH + NaOH
C6H5COOH + Zn
.
2- +

.+ .
+..
.+ +

+ 2

+ 2||

2. .
+2

CH2
H+
A

+ K2Cr2O7

H+

C4H8O

67

 2001 -

+r2

+2KOH

+Na

Z +H2

3.
. 3,448%

.

1. .. 1 8 :
.
.
..

2. :
C20H40...
C4H10....
C3H6..
C5H12.
C10H18..
3. :
CH3 - CH2 - CH2 - CH3..............................................
CH3 - CH2 CH = CH - CH3..
CH3 - CH2 C CH.
CH2 CH - CH CH CH3.

68

 2001 -

CH3 CH3 CH3

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

CH3
CH3 CH2 CH2 C=
CH3 CH CH2 CH = CH2

OH
CH3CH2COOCH3..........................................................
CH3COCH3................................................................
CH3-CH2-O-CH2-CH3.......................................................
CCI3-CH2-CH3..............................................................
CH3-CH2-CH2Br...............................................................

4. :
CH3 - CH2 CH = CH2

CH3 CH - CH2 - COOH

CH3

CH3 - CH - CH2 - CH3

OH
CH2 CH - CH2 CH - CH3
69

 2001 -

CH3

CH3

CH3 CH CH = CH2

CH3
CH3 - CH CH2 -COOH

CH3
CH3 CH CH3

OH
CH3 CH2 CH2 COOH
CH3 C = C - CH3

CH3 CH3
CH3 CH CH2 CH2 CH3

OH
CH3 CH - CH CH2 - COOH

CH3 CH3
CH3

CH3 CH C CH2 CH3

OH CH3

5. :
2 1 -
3,3 - 1 -

70

 2001 -

2,2,3 - -
2,2 - -
1,2 -
3 -1-

3 - 3 -
1,2,4 2 -


1,3 -
2 -1-
2,3





6. :
C20H40
71

 2001 -

C3H7OH
C3H7CH=O
C4H10
CH3CH=O
CH3COCH3
C3H6O2
C5H11OH
CH2O2
C3H6O2 C5H11OH C4H10 C4H6 C5H10
.

:
1. CH2 = CH2 + HCl
2. CH3 CH = CH2 + Br2

3. CH C CH3 + Cl2

4. CH3 CH -CH3

OH

+
170 C

5. CH3 CH CH3 + NaOH

72

 2001 -

Cl
6. CH3 CH CH2 + 2NaOH

Cl

Cl

7. CH3 CH=O + [O]

8. CH3 CH CH3 + [O]

OH
9. CH2 = CH-CH3 + HBr
10.CH3CH2CH2Br+ NaOH
11. CH2 = CH2 + H2O
12. CH3 CH2 - OH + []

13. CH3CH2OH + CH3CH2COOH

14 CH3 C = CH2 + HCl

CH3
Cl

15. CH3- C -CH3 + NaOH

CH3

16. CH3 C = CH2 + H2O

CH3

73

 2001 -

17.

OH

CH3- C- CH3 + [O]

CH3

18. CH3- CH- CH3 + CH3 CH- COOH

OH
CH3
19. HCH=O + H2
20. CCH + H2O
21. CH3-CCH + H2O
22. N 2-
2
1
C5H10 .
2 , .
?
2
2,24 L , STP , 2,
17,6 g CO2.
i. .
ii. ( STP )
. ( 20%v/v O2 80%v/v N2 )
iii.
?
iv.
/ ?
.
3
21 g 11,2 L H2 STP.
. ;

74

 2001 -
.
.

4
:
. .PVC . 1,1- . .
5
;
6
O
:
2-, 2,2,3,3- , 2,2- , 1,2-
, , 2-.
.
7
2 36g 44,8L
STP. mol;
8
4,48L STP 10,8g
.
. ;
. 10L 500L 20%2
80%N2(v/v) .
;
.
9
10L 200L 20%2 80%N2(v/v)
.
. ;
. ;

10
6 g
.
10,8 g.
.
11
;
12
80% C .
. ;
. 6g 20%2 80%N2(v/v) .
75

 2001 -

1.
2. STP
13
N
.
.
. Br2
. O2 ( )

76

 2001 -

77

 2001 -

78

 2001 -

79