-













































:

:

.

. (.).

. 2

(. ).

-1. 4

-1 6

. . -1. 8

.

. . 10

. . 12

. 14


()

.

:

C920

:

CH3C222-2222-3


:

:

28 d -, d- C-C C-H 109,5.

:

sp3- 4 d -

: . - 35, :

) CH3

CH3CCH2CH2 CH2CH3 ) CH3CH2CHCH2CH2-CH3

│ │ │

CH3 CH3 CH2CH2-CH3

2,2,4. 3.

:

, .

:

1. .

2. ().

3. (. )

4. Li, Na, Mg, Zn:

C9H19Br + Mg --- C9H19MgBr

C9H19MgBr + H2O --- C9H20+MgBrOH

5. - , , :

Cl

H3C-CH-CH2-CH2-CH2-CH2-CH2-CH2-CH3+2HI → H3C-CH2-CH2-CH2-CH2-CH2-CH2-CH2-CH3+HC3+ +I2

6. :

Ni, t

CH3CH2CH2CH2CH2CH2CH2CH=CH+H2 →CH3CH2CH2CH2CH2CH2CH2CH2CH3

7. :

C4H9-I+2Na+I-C5H11 →C9H20

:

( ) - . - -53,7C; - +150,8C. , ().

.

:

1.:

C9H20+14O2 →9CO2 +10H2O

2. :

nV tC

C9H19-H+Br2 → C9H19Br+HBr

)

Br2 → Br-+Br-

)

C9H19-H+Br- → C9H19-+HBr

C9H19-+Br2→C9H19Br+Br-

)

C9H19-+ C9H19-→ C9H19-C9H19

C9H19-+Br-→ C9H19-Br

Br-+Br-→Br-Br

3. . :

t

C9H19-H+HNO3 (.)→ C9H19-NO2+H2O

4. : CH3

AlCl │

CH3CH2CH2CH2CH2CH2CH2CH2CH3 → CH3CH2CH2 CH CH2 CH2 CH2 CH3

5..

C9H20→C5H12+C4H8

:

. , , , .


. (, .)

-1.

:

C9H18

:

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


:

:

27 d - π- . 3 d - 120 . d π -.

:

sp2- , π- p- .

:

1)    2) 3) -

4) .

) CH3-CH2-CH2-CH2-CH2-CH2-C=CH2

CH3

2-1

) CH3-CH2-CH=CH-CH2-CH2-CH2-CH2-CH3

-3

) C4H9 H C4H9 C3H7

C=C C=C

H C3H7 H H

--4 --4

) .

:

.

:

1. :

C18H28→C9H18+C9H20

2. π- .

) :

C7H15-CH-Br-CH3+KOH→CH3-CH2-CH2-CH2-CH2-CH2-CH2-CH=CH2+KBr+H2O

) (t>150C):

C7H15-CH (OH)-CH3→CH3-CH2-CH2-CH2-CH2-CH2-CH2-CH=CH2

) , , :

C7H15-CHBr-CH2Br →C7H15-CH=CH2+MgBr2

) t-500C:

Cr2O3

9H20→ C7H15-CH=CH2

:

( ) . , .

:

.

1.:

C7H15-CH=CH2+HBr → C7H15-CHBr-CH3

2.. :

C7H15-CH=CH2+Br2 →C7H15-CHBr-CH2Br ( )

3.: t,Ni

C7H15-CH=CH2+H2 →C7H15-CH2-CH3

4. ( ) :

H+

C7H15-CH=CH2+H2O →C7H15-CH-CH3

OH

C7H15-CH=CH2+H2SO4 →C7H15-CH-CH3

OSO3H

5. ( ):

C7H15-CH=CH2+2KMnO4+4H2O → C7H15- CH- CH2+2KOH+2MnO2

│ │

OH OH

6. :

n C7H15-CH=CH2 →(-CH2-CH-CH2-CH-)n

│ │

C7H15 C7H15

:

, , ( ) ( ) .


-1.

:

C9H16

:

CH3-CH2-CH2-CH2-CH2-CH2-CH2-C≡CH


:

:

24 d - 2 π- . 2 d - 180 . π p- . d 2 π -.

:

Sp3- , π p- .

:

1) 2) 3) .

) CH3-CH2-CH2-CH2-CH2-CH-C≡CH

CH3

3-1

) CH3-CH2-C≡C-CH2-CH2-CH2-CH2-CH3

-3

) CH3-CH2-CH2-CH2-H2-CH=CH-CH=CH2

1,3

:

.

:

1..

C5H11-CH2-CHBr2-C2H5+2KOH→C9H16+2KBr+2H2O

C5H11-CHBr-CHBr-C2H5+2KOH→ C9H16+2KBr+2H2O

2. .

C5H11-CH3-C≡CNa+Br-CH3→ C9H16+NaBr

:

( ) . , - .

:

1.    , . .

) . :

Br2 Br2

C7H15-C≡CH → C7H15-CBr=CHBr→ C7H15-CBr2-CHBr2

) :

HCl HCl

C7H15-C≡CH → C7H15-CCl=CH2 → C7H15-CCl2-CH3

) ( ) . , .

Hg2+,H+

C7H15-C≡CH + 2 ―→ [C7H15-C(OH)=CH2] → C7H15-C-CH3

2.    .

) :

C7H15-C≡CH + 3[O] + H2O → C7H15-COOH + H-COOH

) :

2 2

C7H15-C≡CH → C7H15-C=CH2 → C7H15-C2-CH3

3.    .

:

.


.

.

-1.

:

C9H19OH

:

CH3C222-2222-2-OH


:

:

9H19→O←H

:

29 d -, d- C-C , C-H , C-O O-H 109,5.

:

sp3- 4 d - .

:

1) 2) 3) .

) CH3-CH2-CH2-CH2-CH2-CH-CH2-CH2-OH

CH3

3-1

) CH3-CH2-CH-CH2-CH2-CH2-CH2-CH2-CH3

|

OH

-3

) C5H11-O-C4H9

:

.

:

1. :

CH3-CH2-CH2-CH2-CH2-CH2-CH2-CH=CH2+H2O→CH3-CH2-CH2-CH2-CH2-CH2-CH2-CH-CH3

OH

2. .

C8H17-CH2Br+NaOH→C8H17-CH2-OH+NaBr

3. . , :

) C8H17-CH=O+2[H]→C8H17-CH2-OH

) C7H15-CO-CH3+2[H]→C7H15-CH(OH)-CH3

4. R-MgBr :

H2O

H2CO+C8H17MgBr→ C8H17-CH2-O-MgBr→ C8H17-CH2-OH

-Mg (OH) Br

:

( ) . .

:

1. O-H.

) :

2C9H19-OH+2K→2C9H19-OK+H2↑

) :

H+

CH3-CO-OH + H-O-C9H19→CH3-CO-O-C9H19+H2O

, OH - .

) . , , , :

[O] [O]

C8H17-CH2-OH→C8H17-CH=O→C8H17-COOH

2. C-O.

) :

H2SO4

CH3C2 C2-2-2222-2-OH→CH3C2 C2-22-22=2+H2O

t>150C

) :

H2SO4

2C9H19OH→C9H19-O-C9H19 + H2O

t<150C

) :

C9H19OH + HBr→C8H17-CH2Br+H2O

:

, .


.

.

.

:

C9H18

:

CH3C222-2222-=O


:

:

C8H17→→O

:

28 d -, d- C-C , C-H C=O 109,5 π ═.

:

sp3- 4 d - .

:

1) 2) .

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

CH3

3

) CH3C222-2і22-CH3

││

O

4

:

.

:

1. :

C8H17-CH2-OH+CuO→ C8H17-H=O+Cu+H2O

2. :

C8H17-HCl2+NaOH→ C8H17-H=O+2NaCl+H2O

:

( ) . .


:

1. C═O.

KCN

) 817-=O + HCN ―→ C8H17-CH-CN

OH

) :

H2O

817-=O + R-MgBr → 817-C-O-MgBr → 817-C-OH

-Mg(OH)Br │

R R

) :

817-=O + 2 → 817-CH2-

) :

OH

H+ │

817-=O + ROH↔ 817-HC

OR

OR

2H= │

817-=O + 2ROH ↔ 817-HC

OR

) :

O O

││ ││

C8H17-CH=O + :S-ONa→C8H17-CH-S-ONa

│ │ ││

OH HO O

2. :

)

817-=O + 2[Ag(NH3)2]OH → 817COONH4 + 2Ag↓ + 3NH3+H2O

) 817-=O + 2Cu(OH)2.→ 817-COO +Cu2O↓ + 2H2O

3. :

:

.


.

-1.

:

C9H18

:

CH3C222-222-CH3

││

O


:

:

CH3C222-222→←CH3

↓│

O

:

28 d -, d- C-C , C-H C=O 109,5 π ═.

:

sp3- 4 d - .

:

1) .2) .3) .

) CH3C222-22і2-CH3

││

O

-3

) CH3C222-2і-CH3

││ │

O 3

2

) CH3C222-2222-=O

:

.

:

1.    :

C7H15-CH-CH3+[O]→ C7H15-CO-CH3

OH

2.    :

Hg2+, H+

C7H15-C≡CH + H2O―――→ [C7H15-C(OH)═CH2] → C7H15-CO-CH3

3.    :

t

Ca(C9H19COO)2 →CaCO3 + C7H15-CO-CH3

4.    :

C7H15-CBr2-CH3 + 2NaOH → C7H15-CO-CH3 + 2NaBr + H2O

:

( ) . , .

:

1. C═O. , :

CN

KCN │

) C7H15-CO-CH3 + HCN ―→ C7H15-C-3

OH

) :

CH3 CH3

│ H2O │

C7H15-CO-CH3 + R-MgBr → C7H15-C-O-MgBr → C7H15-C-OH

-Mg(OH)Br │

R R

) :

C7H15-C-CH3 + 2 → C7H15-CH-CH3

) :

OH

C7H15-C-CH 3 + H-OH ↔ C7H15-C-CH3

OH

2. :

, , . [Ag(NH3)2]OH Cu(OH)2.

:

, .


.

. ... ... ... 8-11 .

. 1996 .

... ... 10-11 . .

. 1993 .


2012 , .