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JEE Advanced levelSingle correct optionDifficulty 3 of 3co037

Bromomethane is heated with triphenylphosphine, the product is treated with a strong base (n-butyllithium), and the resulting ylide is added to cyclohexanone. The organic product is

A1-methylcyclohexan-1-ol
Bmethylenecyclohexane
Ccyclohexanol
D1-methylcyclohexene

Answer: B

CH X_{3} Br

and

PPh X_{3}

give the phosphonium salt, and deprotonation gives

(C X_{6} H X_{5}) X_{3} P = CH X_{2}

. Wittig reaction replaces

C = O

by

C = CH X_{2}

with the double bond fixed exactly there, giving the exocyclic alkene.

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