, , . , , .
, , , . , , , R=H.
, () , , . ,
O II CH3CH2CH2C I H | O II CH3CHC I I H CH3 | O II CH3CH2C | CH3 |
2-- | -2 |
1. .
a) .
, . .
b) . , 200-300 , , , .
O II RCH2OH t,kat RC I H | () + H2 |
2. .
O II 2CH2=CH2 + O2 CuCl2,PbCl2 2CH3C I H |
3. .
O II | ||
HCºCH + H2O HgSO4 [H2 | C=C | H] CH3C |
- | I H |
.
4. , , .
CH3CH2 | + 2H2O [CH3CH2 | ] + 2HCl | ||
1,1- | 1,1- | | ¯ |
O II CH3CH2C I H | + H2O |
, .
.
. , . , , . , . c . , , .
.
|
|
.
t., C | t., C | d420 | ||
O II HC I H | -92,0 | -21,0 | 0,815 ( 20) | |
O II CH3C I H | -123,5 | 21,0 | 0,780 | |
O II CH3CH2C I H | -102,0 | 48,8 | 0,807 | |
O II CH3CH2CH2C I H | -99,0 | 75,7 | 0,817 | |
O II CH3CHC I I CH3 H | -65,9 | 64,0 | 0,794 |
. . sp2 - s- ( і), 120 .
, . . s- p- , - . , = p- , (d-), (d+) : .
. .
1. () , a- .
CH3 | + | OH I KCN CH3CCN I H | ||
a- .
2. , .
O II CH3C I H | + HSO3Na CH3 | OH I CSO3Na ( ) I H |
, . , .
2CH3 | OH I CSO3Na + Na2CO3 2CH3 I H | O II C + 2Na2SO3 + CO2 + H2O I H |
.
3. , (), (R) .
|
|
R | OH I RCH I OC2H5 () |
, ( ).
R | + HOC2H5 | H+ | R | + H2O |
.
4. (Ni, Co, Pd .) .
O II RC + H2 Ni RCH2OH( ) I H |
LiAlH4 NaBH4.
.
5. . , .
O II RC I H | [O] | O II RC () I OH |
a) [Ag(NH3)2]OH ( ) . , , . , " ", .
O II CH3C+ 2[Ag(NH3)2OH t CH3COONH4( ) + 2Ag¯ + 3NH3 + H2O I H |
b) (II).
O II CH3C I H | + 2Cu(OH)2() t CH3 | O II C ( -) + Cu2O¯() +2H2O I OH |
(II) (I). , +2 +1. () . , . , , 2.
. , .
=O | H+ | () |
. .
=O + | =O kat | H I C I H | H I OCO I H | H2CO |
, .
n CH2 = O + H2O HOCH2(OCH2)n-2OCH2OH
()
. - - .
H+ OH- | ||
.
H2O + |
CH2OH / | |||||
. .
:
n | = O + (n+1) | + nH2O | |||||
, "" 1909 . . . , , , , .
|
|
. , , , . () , - , , , , , .
, , , , .
, . , R R'.
, .
, (. ". "), .
1. .
R \ CHOH( ) [O] / R | R \ C=O() + H2O / R |
2. .
R \ CHOH( ) kat / R | R \ C=O() + H2 / R |
3. ( ).
RCºCH + HOH HgSO4 [R | CCH2] R I ø OH | CCH3 II O |
4. , .
CH3 | Cl I CCH3(2,2- ) + 2H2O [CH3 I Cl | CH3](2,2- ) + 2HCl | |
¯ | |||
CH3 | O II CCH3 + H2O( ()) |
5. , , .
O II CH3C I O | O | |
\ Ca( ) t CH3 / | II CCH3 + CaCO3 | |
O II CH3C I O |
, . , , . , , , , . .
.
t., C | t., C | d420 | ||
() | CH3 CH3 | -95,35 | 56,2 | 0,790 |
CH3 CH2CH3 | -86,4 | 79,6 | 0,805 | |
CH3 CH2CH2CH3 | -77,8 | 101,7 | 0,809 | |
CH3CH2 CH2CH3 | -42,0 | 102,7 | 0,816 |
, . , . , , , , - , . , , .
(. ". "), , , .
|
|
1. .
R \ C=O() + H CN KCN CH3 / R | OH I CCN( a- ) I CH3 |
2. .
R \ C=O() + HSO3Na R / R | OH I CSO3Na( ) I R |
, , . . , CH3.
3. .
4. . .
R \ C=O() + H2 Ni / R | R \ CHOH( ) / R |
5. , . . " " (II). ( ) .
. , , , , . , ( ), .