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Organic Reaction Mechanisms II: Electrophilic and Radical Reactions
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Hydroboration, oxymercuration, halohydrin formation
JEE Advanced level
Single correct option
Difficulty 3 of 3
o2201
1-Methylcyclohexene is treated with
Br
X
2
in water and the resulting bromohydrin is then treated with aqueous
NaOH
. The final organic product is
A
1-methylcyclohexene
B
2-methylcyclohexan-1-one
C
1-methyl-7-oxabicyclo[4.1.0]heptane (1-methylcyclohexene oxide)
D
1-methylcyclohexane-1,2-diol
Answer: C
The first step gives trans-2-bromo-1-methylcyclohexan-1-ol, with Br on C2 and OH on the tertiary C1. Base forms the alkoxide, which displaces the adjacent anti bromide by intramolecular SN2. The product is the epoxide.
Practice Organic Reaction Mechanisms II: Electrophilic and Radical Reactions
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