no-e2-reaction-is-observed-when-the-following-stereoisomer-of-2-bromo-1-3-4-trim

Question

No E2 reaction is observed when the following stereoisomer of 2-bromo-1,3,4-trimethylcyclohexane is treated with sodium methoxide. Explain this observation.

2-bromo-1,3,4-trimethylcyclohexane structure showing no E2 elimination with sodium methoxide.
Hint: Examine if there is any hydrogen trans to the leaving group; then see if the two can have a diaxial relationship.

Accepted Answer

For the given compound, when the bromine atom occupies an axial position, there are no hydrogens in axial positions on adjacent carbon, so no E2 elimination takes place.

Answer

For the given compound, when the bromine atom occupies an equatorial position, there are no hydrogens in axial positions on adjacent carbon, so no E2 elimination takes place.

Answer

There are no hydrogens on adjacent carbon, so no E2 elimination takes place.

Answer

Sodium methoxide is not a suitable reagent for E2 elimination.

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