Predict the product for the following sequence of reactions. excess CH,CH,CI 1. KMNO4/NaOH/H2O H2SO4 AICI, 2. Н,о" C(CH3)3 C(CH3)3 СОН CH2CH(CH3)2 COH CH2CH3 I СОН II СОН СОН IV ČH2CH: V III

Organic Chemistry
9th Edition
ISBN:9781305080485
Author:John E. McMurry
Publisher:John E. McMurry
Chapter18: Ethers And Epoxides; Thiols And Sulfides
Section18.SE: Something Extra
Problem 25MP: Predict the product(s) and provide the mechanism for each two-step process below.
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Predict the product for the following sequence of reactions.
excess
CH,CH,CI
1. KMNO4/NaOH/H2O
H2SO4
AICI,
2. Н,о"
C(CH3)3
C(CH3)3
СОН
CH2CH(CH3)2
COH
CH2CH3
I
СОН
II
СОН
СОН
IV
ČH2CH:
V
III
Transcribed Image Text:Predict the product for the following sequence of reactions. excess CH,CH,CI 1. KMNO4/NaOH/H2O H2SO4 AICI, 2. Н,о" C(CH3)3 C(CH3)3 СОН CH2CH(CH3)2 COH CH2CH3 I СОН II СОН СОН IV ČH2CH: V III
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