F ..:.. C = O .. -

O
ll
O
(CH3CH2) 2CuLi + CH ether ll
3CH2C-Cl CH3CH2CCH2CH3 O
ll
C-Cl + (CH3) 2CuLi
ether
-78 o C
-78 o C
O
ll
(CH3CH2CH2) 2CuLi + CH3C-Cl ether
-78 o C
O
ll
C-CH3 กกก
กกก
กก
alkyne กก
ก H2O ก
alkyne ก Markovnikov
H-atom
H กก
R-C≡CH + H 2O HgSO 4
H 2SO 4
H
R-C-CH
ll
O H
6. . Ozonolysis of alkene
R1 R
C=C
2 R4
R 3 + O3
Zn
H 2O
H
R-C=CH
OH
R 1
R 2
tautomerization
C=O +
37
H
R-C−CH
OH
+
O=C
R3 R4
R = alkyl, aryl H
+ Zn(OH) 2
H3C C=C
H
H3C CH3 Zn
H2O C=O O=C H
+ O3 2-methyl-2-butene
H3C H
+
3C CH3 acetone acetaldehyde
39
41
5. . Hydration of alkyne
alkyne กก
ก H2SO4
mercuric sulfate (ก acetylene
acetaldehyde)
R C C R
H 2O
H 2SO 4
HgSO 4
HgSO4 HC≡CH + H2O H2SO4 R
H
C C
Enol
R
OH
(less stable)
H
HgSO4 CH3C≡CH + H2O CH
H 3C=CH
2SO4 OH
ก ก
1. CH 3CH 2CH=CHCH 2CH 3 + O 3
2. + O 3
3.
C CH 3
CH 3
H−C=C−H
H OH
Zn
H 2O
Zn
H 2O
R
C
H H
O
C
Ketone
H
CH3−C−CH ll
O H
acetone
38
H 3C−C−H
ll
O
acetaldehyde
H
H
C=O + O=C
H3C CH2CH3 1. O 3
2. Zn, H 2O
40
42
R
7