CH CH CH H H CH CH CH H H O O O O Cl H CH CH CH H H O

【問題】(E)-2-penteneまたは(Z)-2-penteneと次の試薬を反応させた時に得られる主生成物の構造を、
立体化学も明記して示せ。 1) MCPBA, 2) CHCl3, KOC(CH3)3, (CH3)3COH, 3) CH2I2, Zu-Cu, (CH3CH2)2O
ラセミ体
O
Cl
H
CH3CH2
O
O
H
H
CH3
O
CH3CH2
H
CH3
H
H
CH3CH2
H
CH3
CH3CH2
CH3
O
H
ラセミ体
O
Cl
H
O
O
H
H
CH3CH2
O
H
CH3
H
CH3CH2
H
O
CH3
Cl
Cl
C
H Cl
(CH3)3COK +
Cl
C
Cl
+ (CH3)3COH + KCl
ラセミ体
Cl
H
CH3CH2
CH3
C
Cl
H Cl (CH3)3COK
Cl
Cl
H C CH3
CH3CH2
H
H
H
CH3
CH3CH2 C H
Cl
Cl
ラセミ体
Cl
H
CH3CH2
H
CH3
C
Cl
H Cl (CH3)3COK
Cl
Cl
H C H
CH3CH2
CH3
H
H
CH3CH2 C CH3
Cl
Cl
H
Zn
+
I
C
H
I
H
I
H
C
H
ZnI
C
H
ラセミ体
H
H
CH3CH2
CH3
Zn(Cu), CH2I2
H
C
CH3CH2
H
H
CH3
H
H
CH3CH2
H
CH3
C
H
H
ラセミ体
H
H
CH3CH2
H
CH3
Zn(Cu), CH2I2
H
CH3CH2
C
H
H
CH3
H
CH3CH2
H
H
C
CH3
H