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

Chapter 7, Problem PROBLEM 7-29

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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. NaOCH3 Br CH3

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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. NaOCH3 Br CH3

ANSWER:

Step 1 of 2

For a compound to undergo  elimination, the leaving group and the H should be present anti-coplanar to each other.

In the chair conf

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