Contrary to what you might expect, the acetal shown below prefers to adopt the c

Question

Contrary to what you might expect, the acetal shown below prefers to adopt the conformation in which the bulky

tert-butyl group is axial. This may seem like an "exception" but in fact it makes perfect sense! Briefly explain this

compound's conformational preference.

Contrary to what you might expect, the acetal shown below prefers to adopt the conformation in which the bulky tert-butyl group is axial. This may seem like an "exception" but in fact it makes perfect sense! Briefly explain this compound's conformational preference.

Explanation / Answer

The tert-Butyl group is present in axial position as the cis- configuration between Me and tert-Butyl results in repulsion between each other and the energy of the molecule increases. When the tert- butyl group is in axial position is less prone to interaction with Me group.

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