,,,
.
. (.).
. 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
│ │ │
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
) .
:
.
:
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. , . .
) . :
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
:
.
:
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 .
. . (.). . 2 (. ). -1.
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