,

1
????? ??????
???
???
???
Å,
1.43
???? ????? sp3 ?????.
0.90
109.0
108.9
1.10
????? ?????? ???? ???? C-O ??? 1.1 ??"?.
110.0
2
??????????
????? - ???
?????
CH3OH
?????
CH3CH2OH
1-???????
CH3CH2CH2OH
n-propanol
2-???????
CH3CH(OH)CH3
isopropanol
2-????-2-???????
tert-butanol
3
?????? ???????-?????
cis-3-hydroxymethyl-chlorocyclohexane
4
??????
?????? ?? ???? ????, ?? ??????? ?????? ???? ??
????? ????? ?????????
5
???????
Pka-log(K)
2CH3CH2OH 2Na?2EtONa H2
CH3OH NaH?2MeONa H2
(CH3)3COH K?t-BuOK 1/2H2
???? ?????? ??????????? ??? ????? ???? ??????
6
????
????????? ?? ????? ?????? (SN1 ?? SN2)
????? ?? ?????? ??????? ?? ?????? ?????????
????????? ?? ??????
7
????? ??? ???????
??????
???? ??????????
????? ???????????? ??????????
RO CH3Br ? R-O-CH3 Br
8
???? ????? ??????
?????? ??????
-Cl
-R3NH
-Cl, -SO2
R-Cl
Cl
9
3 ROH PX3 ? 3 RX H3PO3
XCl, Br
-Br, -H
?3
H
RBr
Br
?3
3 RBr P(OH)3
10
ROH PX5 ? RX X3PO
XCl, Br
???? ?????? ?? ?????? ?????? ?????
11
?????? ?? ????? ??????
-H2O, -H
H
0 C
-HSO4, -H
-H2SO4
50 C
????. ????? ?? ????????? ?? ???
12
?????? ?????
CH3CH2OH O2 ? 2 CO2 3 H2O
1
??????
????? ??????????
2
????
3
N.R
13
???????
K2CrO4
K2Cr2O7
KMnO4
?????? ??????
???? ?????? ???? ??????? ?????? ????????
?????????. ??????
pyridinium chlorochromate
pyridinium chlorochromate