When the following stereoisomer of 2-bromo-1,3-dimethylcyclohexane is treated with sodium methoxide,...

Question

When the following stereoisomer of 2-bromo-1,3-dimethylcyclohexane is treated with sodium methoxide, no E2 reaction is observed. Explain why this compound cannot undergo the E2 reaction in the chair conformation.

David · Accepted Answer

Br
CH3
CH3
For E2 elimination, the Br substituent and Hs at adjacent carbon should 
be trans to each other. For cyclohexane system, both Br substituent and 
H substituents should preferentially be axial.
Br
CH3
H3C
No trans and axial H at adjacent carbons
high energy conformation

When the following stereoisomer of 2-bromo-1,3-dimethylcyclohexane is treated with sodium methoxide, no E2 reaction is observed. Explain why this compound cannot undergo the E2 reaction in the chair...

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