Thermal decomposition of cyclohexyl-trimethylammonium hydroxide (Hofmann elimination of + CH _2 NMe _3 OH ^- attached to cyclohexane) gives [AMU 2009]

JEE Main Chemistry question

Thermal decomposition of cyclohexyl-trimethylammonium hydroxide (Hofmann elimination of attached to cyclohexane) gives [AMU 2009]

(A)MethylenecyclohexaneCorrect
(B)1-dimethylaminomethylcyclohexene
(C)Cyclohexylmethanol
(D)1-methylcyclohexene

Answer: (A)

Solution

Hofmann elimination (E2, anti-periplanar, base-promoted thermal decomposition of a quaternary ammonium hydroxide) removes a -hydrogen to form the *least* substituted (Hofmann, not Zaitsev) alkene, with loss of trimethylamine and water. From a

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Question ID VK-142174