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Question

The product formed when
1,2-Dimethylcyclohexene is treated with HBr is:

A
cis-1-Bromo-1,2-dimethylcyclohexene
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B
trans-1-Bromo-1,2-dimethylcyclohexene
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C
1-Bromo-1,2-dimethylcyclohexene - both cis and trans isomers
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D
1,2-Dibromomethylcyclohexane
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Solution

The correct option is C 1-Bromo-1,2-dimethylcyclohexene - both cis and trans isomers
Addition of HBr takes place via carbocation intermediate formation
Br can connect to carbocation which is planar on either side. So, two product are formed. A mixture of cis and trans isomers is formed.


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