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

Hint: Examine if there is any hydrogen trans to the leaving group; then see if the two can have a diaxial relationship.

• A. 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.
• B. 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.
• C. There are no hydrogens on adjacent carbon, so no E2 elimination takes place.
• D. Sodium methoxide is not a suitable reagent for E2 elimination.