When the following stereoisomer of 2-bromo-1,3-dimethylcyclohexane is treated withsodium methoxide, no E2 reaction is observed. Explain why this compound cannotundergo the E2 reaction in the chair conformation.

When the following stereoisomer of 2-bromo-1,3-dimethylcyclohexane is treated withsodium methoxide, no E2 reaction is observed. Explain why this compound cannotundergo the E2 reaction in the chair conformation.

Organic Chemistry

9th Edition

ISBN:9781305080485

Author:John E. McMurry

Publisher:John E. McMurry

Chapter11: Reactions Of Alkyl Halides: Nucleophilic Substitutions And Eliminations

Section11.9: The E2 Reaction And Cyclohexane Conformation

Problem 19P

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Concept explainers

Alkynes

Alkynes are organic compounds that contain at least one triple bond between carbon-carbon atoms. They are a series of unsaturated compounds with a general molecular formula, CnH2n-2.

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.

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