%CE%9F%CF%81%CE%B3%CE%B1%CE%BD%CE%B9%CE%BA%CE%AE+%CE%A7%CE%B7%CE%BC%CE%B5%CE%AF%CE%B1+%CE%92+%CE%9B%CF%85%CE%BA%CE%B5%CE%AF%CE%BF%CF%85

1

1.1 ..............................................................................1

1.2 I.U.P.A.C. ...................26

1.3 .............................................................................................................46

1.4 ..........................................................................63

2

2.1 ................................................................73

2.2 .................................................................................................81

2.3 .........................................................................................100

2.4 ............................................................................................117

2.5 .....................................................................145

2.6 ...........................................................................................................173

2.7

.........................................................................................................177

3

.................................................................................................................185

3.1 () ...................................................................187

3.2 ....................................189

3.3 .....................................................................................194

3.4 ...........................................................................................................231

3.5 .......................................................................240

3.6 ...................243

3.7 GRIGNARD................................................................................244

4

..................................................................................................245

4.1 - CH3COOH............247

4.2 2-- ..........................................................251

4.3 ....................................................................................................253

4.4 ............................................................257

4.5 .....................................................................................258

4.6 HCOOH, (COOH)2..............................................................................259

1

1

1.1.

.

: pi (CO), (CO2), (H2CO3) (pi.. CaCO3), ( , pi.. CaC2) (NH4OCN).

: C, H, O, N, Cl, Br, I pi F, S, P (pi.. Fe).

: , pi pi

pi pi pi pi .

, pi, , pipi ..

pi, pi pi . Whler pi (H2NCONH2), pi , , pi .

NH4OCN H2NCONH2

: . , pi, pi, DNA . pi pi

.

6C : : 2e , L: 4e : , pi

C. , .

pi ,

, C. C pi pi, pi pi , pi .

()

. pipi . 2

: . pi .

. , pi pi

, , pi pi

.

H2O -

pi pi

pi pi

pi

pi

pi

pi ,

pi

. pi (..): pi .

..: pi C2H4 pi 2 4 .

. pi (..): , pi pipi pi pipi

.

| | ..: C = C pi pi CH2 = CH2 | | H H

. pi: pi pipi

.

..: C = C

H H

= 120

3

.

. : , , pi.

| | | | | .. C C , C C = O , C C N | | | |

. : pi pi pi

.

| | | .. C = C , C C , C C C | | |

.

. :

| | | | | | .. C C C , C C C | | | | | | C |

. : .

C C .. | | C C

, pi pi

C, , pi .

|| C / \ C C | |

. pi pi

.

..: pi pi pi

(CH4, C2H6, ..).

| | C C | | C C \ / O

. pipi . 4

pi

pi pipi .

pi

:

. C . pi

pi.

.

pi pi pi ( CH2 ). . pi pi () pi. .

.

(H/C)

C () pi

H/C pi CH2 + 2 RH 1

H/C pi

C = C | |

CH2 2

H/C pi

C C CH2 - 2 2

H/C pi CH2 2 3

:

R CH2+1, pi . = 0 . pi (CH2+1) pipi pi (CH2+2) .

5

() pi (.)

| C OH |

CH+1OH CH2+2O 1 ROH

| | C O C | |

CH2+1OCH2+1 CH2+2O 1, 1 ROR 2 + =

C H CH = O || O CHO

CH2+1CHO CH2O 0 RCHO 1

| | | C C C | || |

CH2+1COCH2+1 CH2O 1, 1 RCOR 3 + =

C OH COOH || O

CH2+1CO CH2O2 0 RCOOH 1 + 1 =

| C O C COO C || |

CH2+1COOCH2+1 CH2O2 0, 1 RCOOR 2 + + 1=

C N CN

CH2+1CN CH2-1 0 RCN 1 + 1=

| C NH2 |

CH2+1NH2 CH2+3N 1 RNH2

X: Cl, Br, I CH2+1X (X=Cl, Br, I) 1 RX

:

) pi . pi

.

) , C . || O

,

.

. pipi . 6

.

1. pi pi pi pi pi : i) C C, ii) C = C, iii) C C C, iv) C = O, v) C O, vi) C N, vii) C N, || O vii) C Cl

pi

, C, 4 pi , pipi 4 pi ( ). , , pi.

, , pi.

, , pi.

(Cl, Br, I, F) pi. :

H H H H H H | | | | | | i) C C ii) C = C iii) H C C C H iv) C = O | | | | | | H H H H H H H H | | v) H C OH vi) H C N vii) H C N || | | O H H

2. (C8H18) NaCl (C4H10O); pi pi pipi 2;

pi

(C8H18) , pi (C4H10O). , NaCl , , 2.

3. pi pi : C2H6, HCHO, C2H4, C2H2, CH3COOH, C2H5OH, CH3COCH3, CH3OCH3, CH3Cl. pi pipi pi ; pi pipi .

pi

pi C26 CvH2v+2 ( v = 2). pi :

7

H H | | C C CH3 CH3 | | H H pi C CvH2v+1CHO (v = 0). pi : C ||

pi C24 CvH2v 1 pi ( v = 2). pi :

H H | | C = C CH2 = CH2 | | H H pi C22 CvH2v-2 1 pi ( v = 2). pi : C C CH CH pi C3COOH CvH2v+1COOH (v = 1). pi :

H | C C CH3 C | || H pi C25 CvH2v+1 (v = 2). pi : H H | | C C O CH3 CH2 OH | | H H pi CH3COCH3 (CvH2v)CvH2v+1CC2+1 || , C || (v = 1, = 1). pi :

H H | | C C C CH3 C CH3 | || | || H O H O

9

: ..: CvH2v .. .. 1 CH2 = CH2 C2H4 v = 2 8 C9H18 v = 9

1 2 C 8 9 C. : : ..: CvH2v-2 .. .. 1 CH CH2 C2H2 v = 2 8 C9H16 v = 9

1 3 C, pi pi , 8 10 C. : : ..: CvH2v-2 .. .. 1 CH2 = C = CH2 C3H4 v = 3 8 C10H18 v = 10

:

: ..: CvH2v+1 .. .. H | 1 C CH3 v = 1 | H 8 C8H17 v = 8

: ..: CvH2v .. .. 1 C CH2 v = 1 ||

8 C8H16 v = 8

1 3 C, C pipi || pi , 8 10 C.

: ..: CvH2v .. ..

1 C3 C C3 C36O = 3 || O 8 C10H10 v = 10

1 1 C, ..: C . 8 8 C, ||

. pipi . 10

.

pi .. , CvH2v+1COOH, pi v = 7, .. 8 , C7H15COOH. : : ..: CvH2v+1COOH .. .. 1 C C v = 0 ||

8 C7H15C v = 7

1 C, , 8 9 C. :

: ..: CvH2v+2O .. .. 1 C3 O CH3 C2H6O v = 0 8 C9H20 v = 9

5. pipi pi pi , pi pi ;

pi

I. pi , . H H H H H H H | -4H | | | -2H | | | H C C C H H C C C H C = C C H | | | | | | H H H H H H

..: -4 ..: -2H ..: CvH2v+2-4 CvH2v+2 CvH2v+2-2

-4H H H | | C = C = C | | H H ..:

CvH2v+2-4 CvH2v-2

pi .. CvH2v+2 . 2 pi (..). pi , .. CvH2v, pi .. CvH2v-2. 4 pi (..). .. CvH2v-2.

CvH2v-2 CvH2v-2

. pipi . 12

IV. pi ( ).

H H H | | | H C C C H | | | H H H

..: -2 ..: CvH2v+2 + CvH2v

6. : ) pi C4H10; ) pi C4H8;

pi

) , pi C4H10 (). ) pi C4H8, (): CH2 CH2 | | CH2 CH2

.. H H | | C C C H CvH2v | | || H H

-2

-2

H H | | C C C H CvH2v | || | H H

+

+

13

II.

pi pi :

1. pi pi .

pi

pi pi pi pi

F. Whler (1828), pi pi pi pi (vis vitalis), pi . pi .

2. CH3 C CH3 H C H . || ||

pi

pi pi pi

. , pi

pi pi ,

pi . , pi .

3. pi CH3COCH3 .

pi

| | pi H C C C H. | || | C . ||

4. pi CvH2v+1COOH.

pi

pi CvH2v+1COOH . , pi CxHy(COOH). , pi .

. pipi . 14

5. pi , pi , pi 20. : C:12, H:1.

pi

pi pi pi

( CH2 ), 14. , pi

pipi 14, 14, 28, 42, 56, ... pi .

15

II.

1. pi HCN, Na2CO3, CH2Cl2, NaCl, NaCN, CO2, C2H6, :

. HCN, Na2CO3, CH2Cl2, NaCN, CO2, HCN, C2H6 .

CH2Cl2, C2H6 . Na2CO3, NaCl, NaCN . HCN, CH2Cl2, NaCN, C2H6

2. pi pi pi Whler : . ,

. ,

. ,

. .

3. :

. pi ,

. pi ,

. ,

. .

4. pi pi : CH2 = CHCH3 (I) CH3CH2C N (III) CH2 = CHCCH3 (V) O || || O CH3CCHCH3 (II) CH3CH2C CH (IV) CH3CH2CH3 (VI) :

. ,

. , V, . , V V, . , VI.

5. pi pi pi pi , :

. ,

. pi ,

. pi ,

. .

. pipi . 16

6. pi pi : I. . II. . III. pi . IV. pi pi. V. , pi :

. I, II V. . I, II, IV V. . III IV. . I V.

7. : . , pi,

. , pi,

. , pi,

. , pi.

8. Na2CO3 pi: . .

. (C8H18). . (C3H6O). . pi (C2H5OH).

9. pi: . C10H20 . C5H12 . C6H12 . C5H8

10. pi CH4O : .

.

.

.

11. pi : . CH2, 2 . CH2+2, 1 . CH2-2, 2 . CH2-4, 4

17

12. pi pi C2H4, C3H8, C4H6, C5H10, C2H2, C7H16, C5H8 pi : . C5H10, C2H4, C3H8, . C2H4, C4H6, C5H10, C2H2, C7H14, C5H8 . C3H8, C7H16 . C4H6, C2H2, C5H8

13. pi CH2, 1 : . ,

. ,

. ,

. .

14. pi CxHy : . ,

. ,

. ,

. .

15. pi pi pi :

. C2H6O, . C3H8O, . CH4O, . C5H12O.

16. pi: . R O R . RCOR . RCOOR . R C O R

17. pi CxHyCOOH : . ,

. ,

. ,

. .

18. pi pi : . C3H6 . C4H8

. pipi . 18

. C2H4 . C5H10

19. pi pi ; .

.

.

.

20. pi C4H9 : . ,

. ,

. ,

.

.

21. 5 pi:

. C5H10 . C5H12 . C7H14 . C7H16 . C7H142

22. pi CH3CH2OCH3 : .

.

.

.

23. pi C4H8. : .

.

.

. pi pi pipi

24. pi 10 : . C10H18 . C12H22 . C10H20 . C11H24

19

IV.

1. pi pi pi: . pi pi ....................... pi

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

pi pi

pi pi , pi

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

. ....................... pi pi pi.

pi pi ......................., pi ....................... .

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

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

....................... , , pipi

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

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

pi ....................... .......................

pi, pi pi

pi ....................... ....................... , pi ....................... .

2. pi pi pi ; .

. CH3 CH2 CH3 . CH3 CH = CH2 . CH3 C H || O . H C OH || O . CH CH . CH3 CH2 C N . CH2 = CH O CH3 . CH3 C O CH2 CH3 || O

3. pi :

. CH3 CH CH2 CH3 | CH3 . CH3 CH = CH2 . CH2 CH2 | | CH2 CH2

. pipi . 20

. CH2 CH2 | | CH2 CH2 \ /

// \ . CH CH | || CH CH \\ /

. CH3 C O CH3 || O . CH3 CH2 N CH3 | CH3

4. 1 2 :

1 2 . CH=CH / \ CH2 CH2 \ / CH2

1.

. CH3CH2CH=CH2 2. . CH2 CH2 | | CH2 CH2

3.

. CH // \ CH CH | || CH CH \\ / CH

4.

. CH3CH2CH3 5.

5. pi ; (pi .) . >C = O: . COOH: . CH = O: . OH: | | . C O C : | | . Cl:

NH

CH

CH

21

6. pi C CH3 C pi pi : || . . .

7. 1 2.

1 2 1. CH3CH2 OH . 2. CH3CH || O

.

3. CH3 C CH2CH3 || O

.

4. CHCH . 5. CH4 . 6. CH3COCH3 . 7. HC = O | OH

.

8. CH3 O CH3

8. pi : pi:

. CH2+2 ............................ . CH2 ............................ . CH2-2 ............................ ............................ . CH2+2 ............................ ........................ . CH2O ............................ ............................ . CH2+1COOH ............................

9. pi pi .

. C4H8 . . C3H4 . . 1 C3H6O.

. pi CH2-1OH 1.

. CH4 .

. 3 pi C3H6.

. pipi . 22

IV.

1. pi pi : .

.

.

. ( ) . ( ) .

.

2. pi : . C3H4 . C2H4 . C2H2 . C3H8 . C3H6

3. pi 1 5 : .

.

.

.

4. pi pi pi pi: . CXHYO . CXHYO2 . CXHY

23

V.

pi pi

pi .

pi :

1. pi pi . 2. pi pi

pi pi . ,

pipi .

3. pi pi pi .

1. pi 40; C:12, H:1.

pi C2 2. pi :

r = 12 + 2 + 2 + 16 = 14 2 pi:

14 2 = 40 = 3 pi C3H4.

2. pi pi pi 26,67% ; C:12, H:1, O:16.

pi C2 + 2. pi

r = 12 + 2 +2 + 16 = 14 + 18 (14 + 18)g pi 16g 100 g pi 26,67g pi:

=+

67,2616

1001814

v = 3.

pi C3H8O.

pi % pi

,

pi

pi % pi.

. pipi . 24

3. 4,2 g pi 2,7 atm 1 L, 56C. pi pi . C:12, H:1.

.. C2. :

r = 12 + 2 = 14. pi pi :

PV = nRT PV= .4217,2

)56273(082,02,4MVP

TRmMTRMm

rrr

=

+=

=

pi:

14 = 42 = 3 pi C3H6.

1. 42. pi .

pi: C3H6 2. 5,6 L pipi

18,5 g. pi . pi: C4H10O

3. 1 g , pi 0,82 atm 327 C, 1L. pi .

pi: CH3COOH

4. pi =1,47Lg

pi

1,64 atm 327 C. pi . pi: CH3CHO

5. pi pi pi (CH5N)X, 1 mol pi 5 g ;

pi: CH5N 6. pi C H 1 : 4. pi

.

pi: CH4

25

7. pi pi C H 1:1. pi pipi 3,482 g/L. pi ;

pi: C6H6

8. pi 50% . pi .

pi: CH3OH 9. 2,7 g pi pi

1,7 g NH3. pi ; pi: C4H6

10. pi pi pi pi 55,9 % 127;

pi: C4H8Cl2 11. pi , 1 pi ,

pi pi 16% ; pi: C6H12O

12. pi C H 9:1. pi .

pi: C3H4 13. pi 3,4% S. )

; ) pi 5.734. S pi 1 ;

pi: ) 941 ) 6 14. 0,2 mol pi 6 g C.

pi .

pi: C2H4 - C3H6 15. 0,6 mol pi 10,8 g C.

pi pi .

pi: CH4 C2H6 CH4 C2H4 CH4 C2H2

. pipi . 26

1.2. I.U.P.A.C

.

pi pi , pi

:

1

C.

2

pipi

C.

3 .

(1 C) - (2 C) - (3 C) pipi - (4 C) - (5 C) pi - (6 C) - (7 C) pi ...

(pi ) - - (1 pi ) - - (1 pi ) - - (2 pi ) - - (3 pi ) - -

() () () () ( ) ()

pi 1 3 .

:

CH2 CH2 CH2 CH3

4C pi

CH2=CH2

2C pi

CH3 C CH pi

3C 1 pi

pi

CH3 CH2 OH

2C pi

27

H C OH HCOOH || O

-

1C

:

pi C, pi , 2 pi . pi C 2 .

CH3 CH2 CH ||

pi

3C pi

pi

CH3 C CH3 ||

pi

3C pi

pi

CH3 C ()

2C pi

(R) CH3 : CH3CH2 : CH3CH2CH2 : n-pipi ( pipi)

CH3CH | CH3

:

pipi

CH3CH2CH2CH2 : n- ( )

3 2 1 CH3CH2CH | CH3

:

1--pipi

3 2 1 CH3CHCH2 | CH3

:

2--pipi

CH3 | CH3C | CH3

:

-

. pipi . 28

pi pi : CH3 CH (CH2)v | CH3 v 0 C.

pi sec (secondary = ) C, C pi C.

pi tert (tertiary = ) C, pi C.

(RX) RX, pi .

:

CH3CH2 Cl CH3Br

, , pi () pi, pi , pi pi pi .

:

CH3CH2 Cl CH3Br

(RNH2) RNH2 pi, pi , pi:

RNH2 - - CH3CH2NH2

(ROR ) ROR pi , , .

29

:

CH3 O CH2CH2 CH3 O CH3

(RCOOR ) RCOOR, pi pi pi pi (RCOO), pi (R ) . RCOO R

:

CH3COO CH3 HCOOCH2CH2CH3 pipi

(RCOO pi : Na ) RCOOM , pi pi pi pi .

:

CH3COONa HCOOK

pi pi

1. . pi C pi pipi .

i. CH3CH2CH CH3 iii. CH3CH2CH CH2CH3 | | CH2CH3 CH2CH2OH

ii. CH3CH2CH2C CH3 iv. CH2CH2CH2CH2C CH3 || | || CH2 OH CH2

2. pi pi pi pi pi pi

pipi , pi . pi

. pipi . 30

pipi , pi pi pi

pi . pi pi pi

, pi pi pi pi

.

pi pi pi,

pi . pi

pi , pi pi pi

.

COOH COOR CN CHO

\ / C C C / || \

O

OH NH2 OR

C C > C = C <

| | C C

| |

X R

: 1 2 3 4 i. CH2 = CH CH2 CH3

7 6 5 4 3 2 1 ii. CH3 CH2 CH = CH CH2 CH2 CH2OH

1 2 3 4 5 6 7 CH3 CH2 CH = CH CH2 CH2 CH2OH pi pi pi ( ) pi pi pi . CH3 CH3 | | iii. CH3 CH2 CH CH2 CH2 CH3 CH3 CH2 CH CH2 CH2 CH3 1 2 3 4 5 6 6 5 4 3 2 1

31

6 5 4 3 2 1 1 2 3 4 5 6 iv. CH2 CH2 CH2 CH2 C CH3 CH2 CH2 CH2 CH2 C CH3 | || | || OH O OH O

| | | CCC pi (). | || |

3. pipi (pi pi) pi .

C pi C pi pi pi .

: 1 2 3 4 5 i. CH3 CH = CH CH2 CH3 2pi 3pi

4 3 2 1 ii. CH3 CH2 CH2 CH2 1

1 2 3 4 5 iii. CH3 CH CH2 CH2 CH3 2pi | 1 2 3 4 iv. C C CH2 CH3 1

4. pipi , : ) pipi pi ) pi pi pi , pi

().

: 4 3 2 1 i. CH3 CH = CH C 2

4 3 2 1 ii. CH3 CH = CH CH2 21

6 5 4 3 2 1 iii. CH2 = CH CH2 C CH2 CH3 53 || 5 4 3 2 1 iv. CH2 = CH CH2 CH2 CHO 4pi

: COOH, CN, CHO, pi pi , .

. pipi . 32

5. pi pi pi , pi pi pi. pi

pi pi pi pi pipi pi pi

pi pipi pipi

pi pi pi .

: 4 3 2 1 i. CH3 CH CH2 C 3 | 6 5 4 3 2 1 ii. CH3 CH CH2 CH2 C CH3 52 | || OH O 5 4 3 2 1 iii. CH2 = CH CH CH2 CH2 OH 34pi1 | Cl 5 4 3 2 1 iv. CH3 CH CH2 CH CHO 24pi | | OCH3 OH

6. pi pi pi pi

C pi .

: 5 4 3 2 1 i. CH3 CH2 CH CH2 CH2 31pi | CH3 CH3 | ii. CH3 CH2 CH CH2 CH CH2 COOH 35pi 7 6 | 5 4 3 2 1 CH2CH3

1 2 3 4 5 iii. CH2 = CH CH CH2 CH3 31pi | C3 6 5 4 3 2 1 iv. CH3 C = CH CH2 C CH3 542 | || CH3 O

33

: pi pi

, pi pi pi pi , ,

pi .

, pi , pi .

: 4 3 2 1 i. CH3 CH CH2 CH2 1,3() | OH

1 2 3 4 5 ii. CH2 = CH CH2 CH = CH2 1,4pi

CH3 4 3 | 2 1 iii. CH3 C CH2 CH 3,3 | CH3 CH3 1 2 3 | 4 5 iv. OHC CH C CH2 CH O 2,3,3pi() | | CH3 CH3 v. HOOC COOH ()

7. pi pi .

:

pi pi CH3 (CH2)3 CH3 pi: CH3 CH2 CH2 CH2 CH3 pi. pi pi (CH3)2CH CH3 pi: CH3 CH CH3 2pipi. | CH3

. pipi . 34

.

1. pi 323pi1;

pi

i. (3pi1). 5 4 3 2 1 pi C C C C C pi pi .

5 4 3 2 1 3 C C = C C C

5 4 3 2 1 1 C C = C C C OH

ii. pi, pi 3 2. 5 4 3 2 1

C C = C C C | | CH3 Cl

iii. C pi pi , , C pi 4 . pi : H H | | H C C = C C C CH3 CH = C C CH2OH | | | | | | | H H CH3 Cl H CH3 Cl

2. pi :

pi

CH3COOH CH3CN CH2 = CHCOOH pipi CH3CHO

CH3CH2COOCH3 pipi

CH3CH2CHO pipi

CH3CHCOOCH3 | CH3

-pipi

CH3CCH3 || O

pipi

CH2CCH3 | || OH O

pipi CH3CH2OH

CH3CH2NH2 CH2COOH | OH

CH3 O CH2CH3 CH2 = CH CH3 pipi

35

CH3CH2CH2OCH2CH3 pipi CH3CH2Cl

CH C CH3 pipi CH2 = CHBr 3 2 1 CH3CHCH2CH3 | 4 CH2 | 5 CH3

3pi

CH3CH2NO2

1 2 3 4 CH3CHCH2CH3 | OH

2 3

CH3CHCH3 | CH3

pipi

CH2CH2OH | Cl

2 COOH | COOH

( ) HCHO () 3 2 1 CH3CHCOOH | OH

2pipi 2 1pipi

1 2 3 4 CH3CH = CHCH3 2 3 5 4 3 2 1 CH3CH2CH = CHCH2OH 2pi1 4 3 2 1 CH3CHCHCH3 | | CH3 OH

32

4 3 2 1 CH3CHCHCOOH | | CH3 OH

23

1 2 3 4 5 CH3CH C CH2CH3 | || CH3 O

23pi

1 2 3 4 CH2 = CHCH = CH2 1,3 CH3 1 |2 3 4 5 HOOCCCH2CHCOOH | | CH3 CH3

2,2,4 pi

2,2,4 1,5pi 4 3 2 1 CH3CHCHCOOH | | Cl NH2

23

3. pi : pi

) pi CH3CH2CH2CH2CH = O ) 23pi CH3CH C CH2CH3

| || CH3 O

37

. -

pi pi .

1. pi CH2CH2CH3 1pipi. | CH3

pi

CH2CH2CH3 CH3 CH2CH2CH3 | CH3

pi (), pi pi 4 . . , pi .

2. pi CH3CHCH2CH3 2. | CH2CH3

pi

CH3 | CH3 CHCH2CH3 CH3CH2CHCH2CH3 | CH2CH3

pi (). pi pi , CH3 pi pi , : 1 2 3 4 5 CH3CH2CHCH2CH3 3pi | CH3 , pi .

3. pi CH2=CHCCCH3 4pi2.

pi

pi pi pi

, pi ,

: 1 2 3 4 5 CH2 = CH C C CH3 1pi3 pi .

. pipi . 38

4. pi CH3CH2COOH.

pi

, pi

(COOH). pi CH3 COOH. pi . 8 7 6 5 4 3 2 1 5. CH3CH = CH CH CHCH = CHCOOH I.U.P.A.C.:

| | CH3 CH2CH3

452,6 .

pi

8 C (), 2 pi 2,6 () ( COOH), . pi, 4 5 pi ( pi), . pi .

39

V.

1. pi pipi : . C3H4 . C4H6 . C3H6 . C3H8

2. pi 21 : . C4H8 . C5H10 . C5H8 . C6H12

3. CH3CH = CH CH = O : . .

. .

. 2. . 24. . 2.

4. pi 2 : . C4H8 . C4H10 . C4H62

. C4H6

5. pi 2,32 : . C4H8 . C6H14 . C6H12

. C5H10

6. pi CH C CH CH2OH : | CH3

. 3pi1,

. 14,

. 231,

. 314.

41

11. pi pi : 2,2 22 2,3 331 :

. C4H6Cl . C5H10Cl . C5H8Cl

. C6H14

. pipi . 42

IV.

1. pi pi pi: . pi pipi pi ......................................

.................................... . , pi pipi pipi

. .......................................... , pi ......................................,

.................................. , pi ......................................... .

. pi CH2 = CCHCHCH3 .......................... . | | | CH3 OH CH3

2. pi 1 2.

1 2 CH3 | 1. CH3 C | CH3

. n

2. CH3 CH2 CH | CH3

. (sec)

3. CH3 CH CH2 | CH3

.

4. CH3CH2CH2CH2 . (tert)

3. pi 1 2.

1 2 1. CH2O . 2. CH4O . 3. C2H6O . 4. C2H4O .

4. 1 pi pi 2.

1 2 1. pipi . C4H6 2. 1 . C4H10 3. pipi . C5H10O 4. 2pipi . C6H12O2 5. . C4H10O 6. 3,3 . C3H6

43

IV.

1. pi : . CH3OH . CH3 CH CH3 | OH . CH3 C CH3 || O . HCOOH . CH3CH2OH . CH3 CH2 CH2OH . CH3 CH2 CH CH3 | OH . CH3CH = O . CH3 CH CH = O | CH3 . CH3CH2CN . CH3 CH2 CH2 CO CH3 . CH3 CH2 C CH CH3 || | O CH3

2. pi pi : 1) 2) 3) 1pipi 4) 1 5) 2 6) 2pi 7) 1pipi 8) pi 9) 10) 2 11) 12) 2pi 13) pi 14) pi 15) 16) 17) 1pipi 18)

. pipi . 44

19) pipi 20) 21) 2 pipi 22) 23) pi 24)

3. pi : . CH3CH2CH3 . CH2 = CHCH3 . CH3CH = CHCH2CH3 . CH CH . CH3C CCH3 . CH3CHCH2OH | CH3 . CH3C CHCH3 || | O CH3 . CH3CH CHCH2COOH | | CH3 CH3 . CH3CH = CHCH2C CH . CH2CH2 CH CHCH2CH3 | | |

CH2CH3 CH3 CH3

4. pi pi : . 43,3pi . 36532 . 4pi2 . pi

. () . 5,564pipi3 . pipi

.

. pi() . 1,4()

5. pi : . CH3 CH COOH | OH . CH3 CH2 CH COOH | Cl

45

. CH3 C CH2 CH = O || O . O = HC CH2 C CH2 CH = O || O . HOCH2CH2 CH2 COOH . O = CH CH2 CH CH3 | OH

. (CH3)3C CH COOH | NH2

. pipi . 46

1.3.

.

: pi pi ,

pi .

: :

i. ii.

: pi pi

pi.

: :

i. ii. iii.

: .

:

i. 4 C : C C C C , C C C | C ii. 5 C : C | C C C C C , C C C C , C C C | | C C

: pi pi

.

:

i. C C C = C , C C = C C ii. C C C , C C C | C

47

:

.

pipi:

.. .. ..

CvH2v-2 C3H4 CH3 C CH C3H4 CH2 = C = CH2

CvH2v+2O C2H6O CH3 CH2 OH C2H6O CH3 O CH3

CvH2vO C3H6O

CH3 CH2 CH || O

C3H6O CH3 C CH3 || O

CvH2vO2 C2H4O2 CH3 COOH C2H4O2 HCOO CH3

: pi

pi pi.

. pipi . 50

: C C C C | C ( pi pi pi C 5 pi .) : .

( pi C , pi , 6 pi .) C5H8 : CH CCH2CH2CH3 1pi CH3C CCH2CH3 2pi CH CCHCH3 | CH3 ( .)

5 : C | . C C C C C . C C C C . C C C

| | C C

: i. C = C = C C C, ii. C = C C = C C, iii. C = C C C = C, iv. C C = C = C C. ( C C = C C = C pipi ii C C C = C = C pipi i.)

: i. C = C = C C, ii. C = C C = C . | | C C ( C = C C C pipi ii.) || C

: .

( pi 6 pi .)

C5H8 : CH2 = C = CH CH2 CH3 1,2 pi CH2 = CH CH = CH CH3 1,3 pi CH2 = CH CH2 CH = CH2 1,4 pi CH3 CH = C = CH CH3 2,3 pi

51

CH2 = C = CCH3 | CH3

- 1,2

CH2 = CH C = CH2 | CH3

- 1,3

5. pi C5H10O;

pi

pi CH2O , pi , .

.

5 : C | . C C C C C . C C C C . C C C | | C C || , C , pi .

|| : C C C C C . ( , pi .) : i. C C C C , ii. C C C C . | || || | C C ( C C C C pipi i.) | C =

C | : C C C | || C ( C pi pi pi .) C5H10O :

CH3 CH2 CH2 CH2 CH || O

CH3 CH2 CH CH | || CH3 O

2

HCCH2 CHCH3 || | CH3

3

. pipi . 52

CH3 | CH3 C CH | || CH3 O

pipi

.

5 : C | . C C C C C . C C C C . C C C | | C C

| | , C C C , pi | || | .

: i. C C C C C,ii. C C C C C. || || ( 2 4 ). : C C C C || || C : .

( pi 5 .) C5H10O : CH3CCH2CH2CH3 2 pi ||

CH3CH2CCH2CH3 3 pi ||

CH3 C C - CH3 || | CH3

6. ;

pi

:

1| 2| . C C pipi | | 2 pi. . 1 pipi 2 pi.

53

. 1 pi pipi 2 pi.

. pi, pi

1 pi 2. . i. , 1 2. ii. pi ,

pi 1 pi pi 2.

7. pi C5H12O;

pi

pi CH2+2O. .

.

5 : C | . C C C C C, . C C C C, . C C C | | C C :

i. C C C C C , ii. C C C C C, iii. C C C C C. | | :

| | i. C C C C , ii. C C C C ,iii. C C C C , iv. C C C C | | | | C C C C ( , i. pi iv.)

C | : C C C . | C C512 :

CH3CH2CH2CH2CH2OH 1 pi

CH3CH2CH2CHCH3 2 pi |

55

CH3 | CH3CCH3 11,1- | CH3

CH3CH2CH2CH2CH3 1pipi pipi

CH3CH2CHCH3 2pipi | CH3 pipi

8. pi C5H10O2;

pi

pi CH2O2 , pi , .

.

5 : C | . C C C C C, . C C C C, . C C C | | C C

: C C C C C . || ( pi - C pi .) : i. C C C C , ii. HO C C C C. | || || | C O C C5102 : CH3CH2CH2CH2C pi ||

CH3 CH2 CH C 2-- | || CH3

CH3CHCH2C 3-- | || CH3

. pipi . 56

CH3 | CH3 C C pipi | || CH3

9. pi C5H11Cl;

pi

pi: CH2+1Cl. 5 C. pi , pi :

CH2CH2CH2CH2CH3 | Cl

1--pi

CH3CHCH2CH2CH3 | Cl

2--pi

CH3CH2CHCH2CH3 | Cl

3-pi

CH2CHCH2CH3 | | Cl CH3

1--2--pi

Cl | CH3CCH2CH3 | CH3

2--2--

CH3CH CHCH3 | | CH3 Cl

2--3--pi

CH3CHCH2CH2 Cl | CH3

1--3--pi

CH3 | CH3 C CH2 Cl | CH3

--pipi

57

. -

pi pi .

1. .

pi

pi CH2 , 2. (=4) ..: C4H8. : C C C C (i) C C C (ii) | C :

(i): CH2 = CHCH2CH3 (1-) CH3CH=CHCH3 (2-) (ii): CH2 = CCH3 (-pipi) | CH3 pi pi .

2. pi: CH3CHCH2CH3 CH3CH2CHCH3 | | CH3 CH3 .

pi

pi. 1 2 3 4 CH3CHCH2CH3 2 | CH3

4 3 2 1 CH3CH2CHCH3 2 | CH3

pi pi pi ,

(-CH3) 2 pipi. pi .

. pipi . 58

3. pi: CH3 C CH2CH3 CH2 = C CH2CH3 || | CH2 CH3 .

pi

pi ,

pi. 2 3 4 1 2 3 4 CH3 C CH2CH3 CH2 = C CH2CH3 || | 1 CH2 CH3

2 1 2 1

pi pi pi .

pi .

4. pi: CH3 CH - CH3 CH3CHCH2 | | CH2 CH3 .

pi

pi ,

pi. 2 3 CH3 CH CH3 CH3CHCH2 | | 1 CH2 CH3

2 1 pipi 2 1 pipi

pi pi .

5. pi: CH3 CH2CH3 CH3CH2 -CH3 .

pi

pi pi , .

pi .

59

V.

1. pi pi :

. pi pi,

. pi pi,

. pi ,

. pi pi.

2. pi pi :

. pi pi,

. pi pi

. pi pi

. pi pi.

3. CH2=CHCH2CH3 CH3CH=CHCH3: . ,

. ,

. ,

. .

4. pi pi C5H12 : .

.

.

.

5. 2,3--1-pi : . 2,4--2-pi, . 2,3--1-pi, . 2,3--pi, . 3-

6. pi pi C4H8O : .

.

.

.

. pipi . 60

7. C4H10O : . 4 . . 7 . . 6 . . 5 .

8. pi pi pi C5H10 : . pi

.

.

.

9. 3--1-pi : . 1-pi . 3--pi . 3--1-pi . 3,3--

10. CH3CH = CHCH2CH3 CH CCHCH3 | CH3 .

.

.

.

11. pi C6H12. :

. 3,3--1- . 4--1-pi . 2,2-- . 3--1-pi

61

IV.

1. pi pi pi: ) pi C3H4 : i) pi ............................, pi ............................ ii) pi ............................, pi ............................ . pipi

pi ............................

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

| | ) pi pi C C C | || | ............................ , pi

............................ . pipi

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

) pi C4H10O ............................ ............................ . ............................ .

2. pi pi :

. pi.

. , pi.

. pi.

. pi pi.

3. pi pi ,

pi :

i. .

ii. . iii. pi CH2O2 1 2.

iv. C5H8 9 .

. pipi . 62

V.

1. ; ; pi pipi.

2. : ) ) ;

3. pi pi:

. C5H12 . C5H10 . C5H11 . C5H11 Cl . C5H10

4. pi ..:

C4H9Br, C4H8O, C4H10O, C5H9Br, C4H7COOH, C4H8(COOH)2, C4H8Cl2, C4H5I, C3H6(OH)COOH, C4H8(OH)2, C3H4(COOH)2, CH2O, H2CO2, CH4O.

63

1.4.

.

: pi pi pi

pi .

: .

. 2 CuO. pi ,

pi CO2 pi H2O. () C + O2 CO2

H2 + 21 O2 H2O

CO2 Ca(OH)2 pi , pi CaCO3. CO2 + Ca(OH)2 CaCO3 + H2O

pi pi

.

Ca(OH)2 pi .

: pi pi

pi , pi , pi pi .

: pi pi .

pi pi C 2, pi pi , CO2 (2), pi pi . C 2, pi pi , C 2 pi pi CO2 2 . CO2 , pi pi pi (pi. H2SO4), pi . pi

. pi 2 pi pi

(2) pi . CO2 pi (NaOH, KOH, ..). CO2 pi . pi C pi pi CO2 pi .

. pipi . 64

:

pi pi pi .

pi pi pi . m

. pi pi pi ,

m2 .

m0 = m1 m2.

pi pi

: pi

.

:

pi pi (CH2). pi pi pi pi C.

:

i. pi pi pipi .

ii. pi pi pi pi.

65

I.

pi pi :

1. pi pi C, CO2 pi pi pi , pipi .

pi

CO2 Ca(OH)2 pi , CaCO3. CO2 pipi , pi NaOH, pi (Na2CO3) , pi pi pi . pi pi

pi CO2. pi .

2. pi pi pi pi , pi pi pi CO2 H2O, pi pi pi .

pi

pi CO2 H2O . pi pi CO2 H2O pi pi pi . pi .

3. , CO2 , pi pi pi ,

CO2.

pi

(25 C). , pi

.

pi pi CO2 pi pi . pi .

. pipi . 66

II.

1. pi , pi CO2, pi : . H2SO4 . P2O5 . NaOH . KOH . Ca(OH)2

2. pi pi C H, CO2 :

. pi pi .

. pi pi .

. pi pi

pi pi pi .

. Ca(OH)2

3. pi pi :

. pi pi pi CO2. . pi pi pi H2O. . pi pi pi CO2 H2O. . pi pi pi pi

.

4. pi pi pi 1,5 mol C 3 mol H, ..: . (CH)X . (CH2)X . (C1,5H3)X . (C3H6)X

5. pi pi pipi : . .

. % . . pi .

. pi .

67

V.

. pi % (% w/w) pi pi pi pi.

1. pi % pi C pi pi: ) CH2 , ) C3H8. C:12 H:1.

) CH2 : r = 12 + 2 = 14. : 14 g pi 12 g C 100 g pi ; 85,7 gC pi % pi C CH2 : 85,7% gC. ) C3H8 : r = 312 + 81 = 44 : 44 g pi 36 g C 100 g pi ; 81,8 gC pi : 81,8% C.

1. pi % w/w pi C C2H2. pi: 92,3 %

. pipi . 68

. pi pi pi

(..) .

1. pi pi pi pi pi (..). . , pi

pi (pi % ..) pipi , pi mol .

. mol pi pi pi mol . . mol , pi pipi , ,

.

. mol . pi , pi pi

.

2. pi pi pi pi . pipi pi pi

(r) . . pi pi:

i) pi , pi, .

PV = nRT PV = PV

TRmMTRMm

rr

=

pi Vmp = , pi

PTRpM

PVTRmM rr

=

=

ii) (m) (V) pipi .

V4,22mM

4,22V

Mm

4,22V

Mm

n rrr

====

. pi

pi pi pi pi

. pi pi pipi, pi pi

pi pi,

.

69

1. pi pi 64,86% C, 13,51% 21,63% . pi 74; C:12, H:1, O:16

. pi pi % w/w mol :

mol C = 405,512

86,64=

mol H = 51,13151,13

=

mol C = 352,116

63,21=

. mol pi pi mol :

mol C = 4352,1405,5

mol = 10352,1

51,13

mol = 1352,1352,1

. mol pi pi . mol . pi pi pi : (C4H10O). . pi pi pi, ,

pi:

Mr = (124+110+161)=74 74. pi : 74 = 74 = 1. .. C4H10O.

1. pi pi 48,63% 8,11% . pi pi .

pi: (C3H6O2) 2. pi pi : 2,1%

, 12,8% C 85,1% Br. pi pi 1 g pi 765 mm Hg 140 C 179 cm3.

pi: C2H4Br2

. pipi . 70

3. pi 85,7% C 17,34% . pi 2,308 g/L 30 C 750 mm Hg. pi ;

pi:C4H10 4. pi 85,7% C , pipi

, 1,87 g. pi . pi:

pi

1. pi pi C . 15 g , pi , 33 g CO2 18 g 2. i. pi pi ; ii. , 77 C pi 0,574 atm, pi 1,2 g/L, pi pi ; C: 12, H:1, O:16.

i. pi 15 g , pi C pi CO2 H2O . pi CO2 2 pi pi C H pi pi 15 g .

44 g CO2 pi 12 g H 33 g CO2 pi x1; g C

x1 = 12 4433 = 9 g.

18 g H2O pi 2 g H. pi, 15 g pi 9 g C 2 g H. pipi (1592) = 4 g . pi pi pi

pi:

mol C = 75,0129=

mol H = 212=

mol = =164

0,25

mol :

mol C = 325,075,0

=

mol H = 825,02

=

pi

pi

pi

pipi

pi

.

71

mol = =25,025,0

1

mol pipi . pi mol , pi pi :

pi pi: (C3H8O)v.

ii. pi pi r :

PV = nRT PV = = TRVmMPTR

Mm

rr

+

=

==574,0

)77273(0082,02,1P

TRMTRMP rr

r = 60. pi pi pi, v, pi:

r = (123 + 18 + 161)v = 60v. pi, :

60v = 60 v = 1. pi C3H8O.

1. 8 g pi , pi 22 g CO2 18 g . pi , pipi , 11,2 L. pi .

pi: CH4 2. 0,61 g , pi pi pi C, H ,

pi pi pi pi: 0,44 g CO2, 0,27 g . 1,22 g pi 0,28 g N2. pi, 1 g , pi 623,2 mmHg 337oC, 1.000 mL. pi .

pi: CH3NO2 3. pi pi 6 g , pi 1,2

g C 0,4 g H. pi 6 g pi 3, pi pi 200 mL HCl 1 M. 1 mol pi 28 g , pi.

pi: CH4N2O

. pipi . 72

4. pi pi pi:

i. pi pi , . ii. pi pi 2,3 g , 3,3 g CO2. iii. 0,92 g , pi 0,08 g .

) pi pi . ) pi , 197C pi 0,41 atm, pipi 10-3 g/mL. pi pi pi

pi .

C:12, H:1, O:16. pi: ) (C3H8O3)v, ) C3H8O3 - 92

5. pi C, . 5,8 g pi 2,05 atm 1,4 L 77C. , pi pi pi C ,pi 85,7% C r = 42. C pi . ,

pi .

pi: C3H6O C3H6

73

2

2.1.

.

: , ,

pi ,

.

: pi pi pi

pi pi pi .

: pi .

: pi pi pi

pi (, , , , ..) pi pipi .

pi pi

pi pi pi pi, pi,

, pipi ..

: 5 12 . pi: .

pi:

) pi pi pi. ) pi, , pi,

pi pi pi pi pi

pi . pi

.. C13H28 C8H18 + C5H10

: pi .

pi

. pi pi

. pi pi

, pi pi pipi pi

pi .

. pipi . 74

CH3 pi |

.. CH3CH2CH2CH2CH2CH2CH2CH3 CH3 C CH2 CHCH3 | |

CH3 CH3

: .

pi: pi pi.

: pi pi , 2 CH4, C2H4, C3H6, C4H8, C6H6 (). pi pi pi pi pi.

75

.

1. pi pi; pi ;

pi

pi pi

pipi 400C. pi pi . pi ,

pi, pi pi, pi

pi, pipi.

pi C pi pi

.

pi, pi

, pi pi

pi (pi ). pi (pi pi ) pi pipi pi.

, pi pi

.

pi pi .

pi , pipi

( pipi ).

. pipi . 76

II.

1. pi pi pi: . .

.

pi ,

.

. pi ,

.

. .

2. pi pipi: . .

. pi.

. pi.

. .

3. pi pi : . pi.

. .

. pi, , .

. pi pi.

4. : . pi pi pi pi.

. pi pi , pi pi pi

pi pi.

. pi, pi pi pi.

. pi pi

pi.

5. : . 5 8 . . .

. .

. 5 12 .

77

6. pi: . pi pi , pi .

. pi pi , pi .

. pi , pi .

. pi , pi 2.

7. pi pi : . pi pi pi

.

. pi pi pi.

. pi

pi pi .

. .

8. : . pi .

. pi .

. pi pi .

. pi

.

9. pi pi pi: . .

. .

. pi.

. pi.

10. : . .

. .

. .

. pi.

. pipi . 78

IV.

1. pi 1 2, :

1

pi

2

) ) ) ) )

) ) )

i) ii)

iii) iv) v) vi) vii)

viii)

pi

pi

pi

2. pi . pi : , pi

pi pi ...................... , pi

................................ . pi, pi ,

pi .................... . pi .................... ,

pi pi pipi ........................... .

3. pi pi pi pi ; i. pi pi

pi.

ii. pi pipi pi .

iii. pi pi pi pi.

iv. 10 14 .

v. pi .

vi. . vii. pi pi

pi (Cracking Process). viii. .

79

4. :

1 2 ) ) pi ) ) ) ) )

i) 161C ii) 69C iii) 88C iv) 0,5C v) 42C vi) 30C vii) 192C

5. pi pi pi pi, pi

:

i. .. ii. .. iii. .. iv. .. v. ..

vi. .. vii. ..

i. ii. iii. iv. v. vi. pi vii. pi

6. pi pi pi. ) pi pi pi ......................................................... . ............................ pi , pi

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

) , pi ......................., pi , ........................... .

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

pi .................................... .

. pipi . 80

V.

1. pi, pi , pi pi pi pi pi ;

2. , pi pi pipi;

3. pi;

4. ;

5. pipi pi pi ;

6. pi pi pi;

81

2.2. -

.

: , pi pi

.

: pi pi pi

pi: pi pi

( ..), (, diesel ..) : (), () ( )

.

: pi pi pi pi

pi . pi

31 MJ/Kg. 1 Kg pi 31 MJ.

pi

:

) , pi CO2 ( ). C + O2 CO2

) pi CO ( ) C +

21

O2 CO

(H/C) ) : , pi pi ,

pi CO2 H2O. C2H4 + 3O2 2CO2 + 2H2O ) : pi CO , pi

C (). 2 pi pi 2. C2H4 + 2O2 2CO + 2H2O

C2H4 + O2 2C + 2H2O

:

pi pi pi

.

. pipi . 82

.

1. pi : ) )

pi

) 4 pi CH2+2. pi : C4H24+2 C4H10 ( =4) pi C4H10 CO2 H2O

C4H10 + O2 CO2 + H2O .

4 C C4H10, 4 CO2 10 C C4H10, 5 2O

C4H10 + O2 4CO2 + 5H2O pi : 42 + 5 = 13 .

2

13 2

C4H10 + 213 O2 4CO2 + 5H2O

) pi CH2+2O. pi : C2H22+2O C2H6O (=2)

pi C2H6O (CO2 H2O) .

C2H6O + O2 2CO2 + 3H2O : 22 + 3 =7 pi 7 , 1 pi pi C2H6O, pi pipi pi 6 . 3 2 .

C2H6O + 3O2 2CO2 + 3H2O

2. : ) )

pi

) pi CH2+2. pi CO2 H2O

CH2+2 + O2 CO2 + H2O C , CO2.

83

2 + 2 , 2

)1(22

22 +=

+=(+1)

2.

CH2+2 + O2 CO2 + (+1)2 pi 2++1 = 3+1 pi

2

13 + 2 .

CH2+2 + 213 + O2 CO2 + (+1)H2O

) pi CXHY. pi (CO2 2)

CXHY + O2 CO2 + H2O x C , x CO2

y , 2y

2

CXHY + O2 XCO2 + 2y H2O

2x + 2y

=

2yx4 +

pi

=

+

22

yx4

4yx4 +

2 .

CXHY + 4yx4 +

XCO2 + 2y H2O

. pipi . 84

II.

1. : . pi pi pi .

. pi pi pi

. pi pi pi

. pi pi pi

.

2. pi, , : .

.

.

.

3. pi pi, : .

.

.

.

4. : .

. pi ,

. pi pi

. pi pi

5. 21 MJ/Kg. : . 1 Kg pi 21 MJ . 1 Kg pi 21103 J . 1 Kg pi 21106 J . ( )

85

IV.

. pi

pi.

pi pi () pi pi (pi) . pi

pi . :

i. , mol pi .

ii. , , pi .

mol ( pi ) pi . pi pi

pi pi . pi

pi.

.. pi CH4: CH4 + 2O2 CO2 + 2H2O

:

1mol CH4 2 mol 2 pi 1mol CO2 2mol 2 1L CH4 2 L 2 pi 1L CO2 2 L 2 ( pi ).

pi pi pi pi

pi. pi pi

:

i. , pi pi, pi .

ii. mol pi ( ) mol pi ( ), .

iii. mol :

) , (m): n = rM

m

) (V), : PV = nRT n =TRVP

STP 1 mol 22,4 L ; n mol V L

. pipi . 86

1. 32 g CH4 pi . , pi CO2 pi pi; pipi pi. : ArC: 12, ArH: 1.

pi mol CH4. CH4 r = 12 + 41 = 16

n = 2nmol1632

Mm

r

== mol

pi mol pi:

CH4 + 2O2 CO2 + 2H2O 1 mol 2 mol 1 mol 2 mol 2 mol = ; = ; = ;

= 4 mol O2 = 2 mol CO2 = 4 mol H2O

pi mol g L (pipi ). 2: V = n22,4 = 422,4 V = 89,6 L CO2: V = n22,4 = 222,4 V = 44,8 L H2O: m = nMB = 418 m = 72 g

2. (pi 20% v/v 2) pi pi 10 L ; pi.

pi pi

pi, mol .

pi 2, pi

pi .

C2H6 + 27 O2 2CO2 + 3H2O

1 L 3,5 L 10 L x = ; x = 35 L O2

87

pi , pi

pi .

100 L pi 20 L O2 V=; pi 35 L O2 V = 175 L .

3. pi pi pi 0,741 g/mL: . pi pi mol pi . .

.

. ( pipi ) ; . pi pi pi

35 MJ/kg. : C:12, H:1

. pi pi:

g741mL 1000mL

g 741,0VmVm

==== .

pi pi , ..

C8H18 Mr = 812 + 181 = 114.

mol 5,6114741

Mm

nr

=== C8H18

. C8H18 + 2O225 8CO2 + 9H2O

. 1mol 8 mol 1mol 8 22,4 L (pipi ) 6,5mol x; x = 6,5 8 22,4 = 1164,8 L CO2 . pi pi pi pi

, 741 g . : : 1kg 35 MJ : 0,741 kg ; MJ

= 0,741 35 = 25,935 MJ

. pipi . 88

4. 4,4 g pi 7,2 g . pi pi .

: C:12, H:1, O:16.

pi CH2+2 Mr = 12 + (2+2)1 = 14+2. 4,4 g x mol :

2144,4

x+

= (1)

CH2+2 + 213 +2 CO2 + (+1)2

1 mol (+1) mol x mol ;=(+1)x mol pi (+1)x mol 2 pi 7,2 g. 2 :

r = 16+21 = 18 :

)2( 1

4,0x4,0x)1(

182,7

x)1(M

mn

r

OHOH

22 +

==+=+=

pi (1) (2) , pi: 3

14,0

2144,4

=+

=+

pi C3H8 pipi.

1. 56 g pi pi . : . pi pi pipi .

. pi pi.

pi 20% v/v 2. pi: . 672 L, . 72g

2. 10 L C3H8 pi pi . . pi

.

pi: 30 L CO2, 40 L H2O 3. 71,25 L.

pi pi

=0,8 g/mL 35 MJ/kg, pi: . kg CO2 pi .

. pi pi pi

500 km. 1 L 10 km.

89

. KJ/mol. pi: 176kg CO2, 1400MJ, (0,3 10-3) KJ/mol

4. 4,4 g 32 g 2 pi 7,2 g . pi pi 2 pi pi.

pi: C3H8, 16g 5. 6 g , , 6,4 g 2.

pi .

pi:HCHO 6. CXHY, pi O2 pi

pi pipi .

pi

pi:

. pi

. pi .

pi: . C410 . , -pipi 7. , , pi CO2

pi ; pi: C2H4

8. pi 0,72 g/mL. 10 mL pi , pi pi 22 g CO2 21,6 g H2O. pi .

pi: C5H12

. pipi . 90

B. pi . CuO.

pipi :

. pi (pi H2SO4, CaCl2, P2O5) pi . (H2O) pi pi pi . pi,

, pi pi pi ,

(2). . , pi ,

pi , pi CO2. pi CO2 pi pi pi . pi

, pi pi pi ,

CO2.

:

pi ,

, pi CO2, pi pi .

. pi 2 pi pi pi

, pi 2.

pi pi

2. pi

, 2 pi pi pi

. pi pi pi

pi , 2 pi pi pi

.

. pi ,

( 25 C) pi . pi pi

(H2O). pi , pi pi , pi pi pi

pi.

. pi pi pi CuO pi , pi 2. pi:

CH4 + 4CuO CO2 + 2H2O + 4Cu pi pi, pi pipi , pi

CuO, pi Cu.

91

m m = mCuO () mCu = nCuO Mr CuO nCuAr Cu = nCuO(Ar Cu + Ar O) nCuO Ar Cu = nCuO Ar O = nCuO = 16, pi nCuO mol CuO pi . . ( 2), 2 , pi

. pi, pi ,

20% .. 2 (.. v/v). 100 , 20 2 80 2. pi pipi :

222222 OONOON n5n ,n4n ,V5 V,V4V ====

pi ,

pi pi 2,

. 2

pi 2 pi pi .

. pi pi C CO2 2, CxHyOz ( pi pi pi ), pi pi C , CxHy. , pi pi

C, H, N CO2, H2O 2, CxHyOzNw, pi pi C, H, N CxHyNy. :

CxHyOzNw + 4z2yx4 + O2 xCO2 + 2

y H2O + 2w N2.

1. 8 L 275 L (20% v/v 2, 80% v/v N2) . 7 L . . pi ; . pi pi pi

2SO4; pi % v/v pi ;

. pi CvH2v. pi 7 L , pi.

(pi) :

. pipi . 92

CvH2v + 2v3 O2 vCO2 + vH2O

1 L 2v3 L v L v L

8 L ;2v3 8 L ;v 8L ;v 8L

pi , pi 2 2

pi .

100 L pi 20 L O2 80 L N2 275 L pi x1 ; L O2 x2 ; L N2

x1 = 10027520 = 55 L.

x2 = 10027580 = 220 L.

, pi 7 L , (55-7) L = 48 L . pi :

2v3 8 = 48 v = 4.

pi C4H8.

. H2SO4 . pi pi pi CO2, O2 pi pi pi 2. pi :

=2COV v 8 = 4 8 L = 32 L

=pi )(O2V 7 L

= )(2V 220 L

% v/v pi : V = L 259 L )220732(VVV )(N)(OCO 222 =++=++ pi . 259 L pi 32 L CO2, 7 L O2 220 L N2 100 L pi x3 ; L CO2, x4 ; L O2 x5 ; L N2

x3 = 25910032 = 12,36 L CO2.

x4 = 2591007 = 2,70 L O2.

x5 = 259100220 = 84,94 L N2.

12,36% v/v CO2, 2,70% v/v O2 84,94% v/v N2.

93

2. 6 g pi pi CuO. pi , pi , pi

8,8 g. pi pi CuO pi 6,4 g. pi (6 g) pi V = 8,2 L 127C pi 0,4 atm. pi . : rC = 12, ArH = 1, ArO = 16.

pi CxHyOz. pi pi pi

pi . 6 g mol. pi :

CxHyOz + 2z2yx4 + CuO xCO2 + 2

y H2O + 2z2yx4 + Cu

1 mol 2

z2yx4 +mol x mol

2y

mol 2

z2yx4 +mol

mol ;2

z2yx4 + ;x ;

2y

;2

z2yx4 +

: r = 12x + y + 16z. pi :

= rM

m =

z16yx126++

(1).

, pipi pi

. , CO2. CO2. pi:

2,0x8,844x8,8Mn8,8m222 COrCOCO ==== (2)

pi pi CuO pi :

mCuO mCu = 6,4 nCuO MrCuO - nCu Ar Cu = 6,4

2

z2yx4 + (Ar Cu + Ar O) - 2

z2yx4 + r Cu = 6,4

2

z2yx4 + Ar O = 6,4 2

z2yx4 + 16 = 6,4

(4x + y 2z) = 0,8 (3) pi pi

.

PV = nRT PV=

=

VPTRmMTR

Mm

rr

. pipi . 94

g/mol 60ML 2,8atm 4,0

K )127273(Kmol

atmL 082,0g 6

M rr =

+

= .

12x + y + 16z = 60 (4) pi (1), (2), (3) (4) : = 0,1 mol z = 2 x = 2 y = 4 pi : C2H4O2.

1. 10 L C2H4 200 L . pi pipi pi pipi

pi .

pi.

pi: 160 L N2, 10 L O2, 20 L CO2 2. 1,12 L , pipi , .

, pi pi pi H2SO4, 2,7 g. , pi , 4,4 g. pi .

pi: C2H6 3. 10 cm 50 cm3 2

pi . pi ,

, pi 40 cm3, pi pi 20 cm3 pi NaOH, pipi pi . pi .

pi .

pi: C2H4 4. 5,4 g CuO. pi pi CuO

17,6 g. . pi pi CuO; pi .

. NaOH. NaOH;

pi: . C4H6, . 23 g 5. 2,24 L , pipi ,

Ca(OH)2. , , pi , pi

20 g. pi . pi: C2H4

95

6. pi pi . pi pipi , , 16 pi . pi .

. : 20% v/v O2, 80% v/v N2. pi: C2H4

7. pi pi pi (20% v/v O2, 80% v/v N2) pi pi pi pi . 48 pi pi. ,

pi pi. ( ). pi: C3H8

. pipi . 96

B. .

x mol pi y mol pi . pi , x (L mL) pi , y pi pi .

1. 30 mL pi pi 95 mL , pi pi.

. pi % v/v ; . ;

. pi pi x mL (C2H6) y mL (C2H2). pi. :

C2H6 + 27 O2 2CO2 + 3H2O

mL: x 27

x 2x 3x

C2H2 + 25 O2 2CO2 + H2O

mL: y 25 y 2y y

V = yx30VV 2262 HCHC +=+ (1)

2OV = 95 mL 190y5x795y25

x27

=+=+ (2) pi (1) (2) x = 20 mL y = 10 mL pi pi 20 mL C2H6 10 mL C2H2. (20+10) mL = 30 mL. pi:

30 mL pi 20 mL C2H6 10 mL C2H2 100 mL pi x1 ; mL C2H6 x2 ; mL C2H2

x1 = 3010020 = 66,67 mL.

97

x2 = 3010010 = 33,33 mL.

, pi % v/v 66,67% v/v C2H6 33,33% v/v C2H2.

. , pi.

pi pi . :

mL 60 mL )102202(y2x2V2CO =+=+=

2. L , , pi 8 L 48% w/w C2H6 52% C2H2;

100 g pi 48 g C2H6 52 g C2H2 mol :

6,13048

n62HC == mol

23026

52n

22HC == mol

mol C2H6 C2H2 1,6:2. mol , pi , :

56,36,36,18V

6,36,1

VV

26,16,1

VVV

62

62

2262

62HC

.

HC

HCHC

HC===

+=

+L

L44,4L56,3L8VVV6222 HC.HC ===

:

C26 + 27 O2 2CO2 + 3H2O

3,56 L 27

.3,56 L

C2H2 + 25 O2 2CO2 + H2O

4,44 L 25

.4,44 L

:

56,2344,42556,3

27V

2O =

+= L

. pipi . 98

1. pipi 12 g. . , ,

.

. pipi

, pi

; (pi: pi pi mol pi ).

pi: . 3,2 g, 8,8 g, 4,48 L . 56,8 g 2. pi 100 L pi 60 L CH4 40 L CO2.

pi:

. pi pi 56 L , CO2 pi pi . . pi pi pi pipi

, 1 kg , 20 J.

.

pi: . 336 L , 56 L CO2 . 1,36 MJ 3. pi 27,5% w/w pipi

72,5% w/w . 320 g .

. pi pi ,

CO2 pi pi pi . . pi

56 m3, pi pi ; pi 20 % v/v 2. 24 L.

pi: . 4.320 L O2, 2.640 L CO2 . 38,6%

4. pi , pi pi . 10 L , 12,8 L .

. pi % v/v . . 10 L pi 100 L , pi ; . : 20% v/v O2 80% v/v N2.

pi: . 64% v/v CH4 . 7,2 L O2, 80 L N2, 10 L CO2 5. 5 g pi. pi .

pi H2SO4 pi pi pi pi NaOH. pi NaOH 304,2 g, 313 g. pi:

. pi % w/w pi pi .

99

. .

pi: . 8% w/w . 5,8 g 6. pi pi pi mol 1:2.

(20% v/v O2), pipi , 656 g .

pi: 8064 L 7. 400 L CH4 C2H2, 1:3 ,

(20% v/v O2). . pi pi ; .

. pi % w/w . pi: . 4.750 L . 83% w/w C2H2

8. CH4 C2H4 pi 2 . , 20 cm3. CO2 pi pi 16,5 cm3, pi ; .

pi: 3,5 cm3 CH4 - 6,5 cm3 C2H4 9. CH4, C2H4 C2H6 pi (20% v/v

O2). C2H4 C2H6 . , mol 2 CO2 20:3. pi % v/v .

pi: 20% - 40% - 40% 10. 448 cm3 pipi

0,68 g. , pi pi pi pi pi pi H2SO4 pi pi , pi pi 0,72 g 2,2 g . pi .

pi: C3H4 C2H4 C2H2 C3H6 11. pipi pi 2,277 g/L pipi .

pi pipi pi pi pi

32,4 g pi H2SO4. pi pi NaOH;

pi: 61,6 g 12. pi pi 0,7 g/cm3. pi

pi 0,6 g/cm3 0,8 g/cm3. . pi 2, pipi , pi

pi pi 1 L . . , pi 2 pi pi

pi 1 L . pi: . 1.680 . 10,5 L

. pipi . 100

2.3. -

.

: , pi pi pi, pi

.

:

. , pipi .

. , pi pi. pi

pi pi 60% 40% . . pi pi.

pi: pi, pi

.

pi: pi

pi.

: ( 1-4 C) , , ( 5-16 C) ( 17 C ) . .

1. ) : pi CO2 2.

CvH2v+2 + 21v3 + O2 vCO2 + (v+1)H2O

.. CH4 + 2O2 CO2 + 2H2O ) : pi CO C 2. CvH2v+2 + 2

1v2 + O2 vCO + (v+1)H2O

CvH2v+2 + 21v + O2 vC + (v+1)H2O

.. CH4 + 23 O2 CO + 2H2O

CH4 + O2 C + 2H2O

2. : pi (2: Cl2, Br2).

101

CvH2v+2 + X2 CvH2v+1X + HX

.. CH4 + Cl2 CH3Cl + HCl

CH3Cl + Cl2 CH2Cl2 + HCl

CH2Cl2 + Cl2 CHCl3 + HCl

CHCl3 + Cl2 CCl4 + HCl

i) pi RCOONa ( RCOOK) NaOH ( ), pi pipi C pi .

R COONa + NaO H RH + Na2CO3

.. pi CH4, pi 1 C, pipi 2 C.

CH3COONa + NaOH CH4 + Na2CO3

:

, RCOONa RCOOK, pi (RCOOH) pi NaOH . pi:

RCOOH + NaOH RCOONa + H2O RCOOH + KOH RCOOK + H2O

ii) . CvH2v + H2 Pt CvH2v+2

.. CH2 = CH2 + H H Pt CH3 CH3

: pi pi pipi CH4 pi 1 C.

iii) () (RX) pi .

RX + H2 Pt RH + HX

. pipi . 102

.. CH3Cl + H2 Pt CH4 + HCl pipi pi pipi || (Pt), : RX + 2|H| RH + HX

iv) pi Na ( ) , ( Wurtz). pi pi C pi .

2RX + 2Na R R + 2NaX

:

pi pi CH4 Wurtz, , .

2CH3Cl + 2Na CH3 CH3 + 2NaCl

pi .

pi.

pipi .

. pi pi, pi ,

pi ( ), pi .

pi pi C20H42.

103

.

1. C4H9I. , pi , ;

pi

C4H9 : . CH3CH2CH2CH2 . CH3CHCH2 | CH3 CH3 | . CH3CH2CHCH3 . CH3CCH3 | |

pipi , pi:

. CH3CH2CH2CH2 + H2 Pt CH3CH2CH2CH3 + H . CH3CH2CHCH3 + H2 Pt CH3CH2CH2CH3 + H |

. CH3CHCH2 + H2 Pt CH3CH CH3 + H | | CH3 CH3

| . CH3CCH3 + H2 Pt CH3CH CH3 + H | | CH3 CH3

.

2. pi pi .

pi

i. pi pi 2 C, pi Na ( ), ( Wurtz), pi pi 4 C.

2CH3CH2 + 2Na CH3CH2CH2CH3 + 2Na

ii. pi , pi 2, pi : CH3CH2 + H2 Pt CH3CH3 + H

. pipi . 104

3. pi pi :

pi

i. CH3CH2CH2Cl + H2 ......................Pt

CH3CH2CH3 + HCl

ii. 2CH3X + 2Na ..............................

CH3CH3 + 2NaX

iii. CH3CH2COONa + NaOH ...................CaO

CH3 CH3 + Na2CO3

iv. C4H10 + 213 O2 4CO2 + 5H2O

v. CH4 + Cl2 C3Cl + HCl

vi. CH3Cl + Cl2 C2Cl2 + HCl

4. pi pi : .

. .

pi

. RCOONa ( RCOOK) NaOH ( ), pipi C pi . , pi , CH3CH2COONa NaOH, :

CH3CH2COONa + NaOH C3C3 + a2C3

. i) () RX pi ( ), pi . pi:

CH3CH2X + H2 Pd,Pt C3C3 + HX ii) pi Na ( ) , ( Wurtz), pi pi C, pi:

2CH3X + 2Na CH3 CH3 + 2NaX

105

I.

pi pi.

1. pi pi pipi Wurtz pi .

pi

Wurtz pi (RR). pipi, CH3CH2CH3, . pi .

2. pi 2pipi, Wurtz, pi .

pi

2pipi, CH3CHCH3, (RBr), pi | Br R pipi: CH3CH. | CH3 :

2CH3CHCH3 + 2Na CH3CHCHCH3 + 2NaBr | | | Br CH3 CH3 2,2 pi .

3. ( ) pi .

pi

pi pi RCOONa NaOH ( ), pipi pi .

RCOONa + NaOH RH + Na2CO3

pi, pi (1 C) pi (1 C). , pi 2:

H COONa + NaO H H2 + Na2CO3

pi .

. pipi . 106

4. NaO pi pi pipi.

pi

pi pi pipi

:

C3CH2CH2COONa + NaOH CH3CH2CH3 + Na2CO3

() pi pi pi NaOH .

C3CH2CH2COO + Na OH CH3CH2CH2COONa + H2O

pi pi pi pipi,

pi NaOH pi pi pi NaOH. pi .

107

IV.

1. : . pi

,

. CH4 CO, . CO 2, . CO.

2. : . CH4 CO, . pipi pi ,

. pipi pi pi pi pi

, pi ,

. pi , pi pi.

3. CH4 pi: . ,

. ,

. ,

. pi .

4. : . , , , pi

,

. , , , pi

,

. , , , ,

. pi , , , .

5. : . pi pi ,

. ,

. pi pi pi ,

. .

6. , pi pi : . ,

. ,

. , ,

. , .

. pipi . 108

7. : . pipi , pi ,

pi pi pi,

. pipi pi pipi ,

. pipi , pi ,

pi pi,

. pi pipi pi .

8. : . pipi,

. pipi ,

. ,

. .

9. pi : . ,

. ,

. ,

. .

10. pi pi: . C20H42 . C15H32 . C7H16

. C3H8

11. pi pipi NaOH, pi: . pipi ,

. ,

. , ,

. .

12. 2 pi, pi: . 2 pi, . 2 2 pi, . 3 pi, . 3 1 pi.

13. pi 22, pi Pt, pi: . 21, . 2,

109

. 2, . .

14. pi Na pi : . ,

. ,

. Na , .

15. pi 2pipi , pi:

. pipi,

. 2,3, . ,

. 2,2.

. pipi . 110

V.

1. pi pi pi: . pi

pi , pi pi pi % , % pi .

2. pi pi . . :

. : ..

. :

. : ..

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