The quaternary ammonium hydroxide shown is heated (Hofmann elimination). Which structure is the major organic product besides trimethylamine or water?

AStructure A
BStructure B
CStructure C
DStructure D

Answer: D

The salt is 2-methylbutan-2-yl trimethylammonium hydroxide. By the Hofmann rule the base removes a hydrogen from the least substituted beta-carbon (a methyl group), giving 2-methylbut-1-ene. The more substituted 2-methylbut-2-ene is minor, while the amine and alcohol are not formed in significant amounts at high temperature.

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