The reaction of unactivated chlorobenzene with sodium amide () in liquid ammonia yields aniline. The reaction proceeds via an elimination-addition mechanism involving which highly reactive intermediat

Question

The reaction of unactivated chlorobenzene with sodium amide ($NaNH_2$) in liquid ammonia yields aniline. The reaction proceeds via an elimination-addition mechanism involving which highly reactive intermediate?

Prashant Kotian · Accepted Answer

Correct answer: C. Unactivated aryl halides require extremely strong bases (like NaNH2) to react. The base removes an ortho proton, expelling the halide to form a benzyne intermediate containing a highly strained, external sp2-sp2 "triple bond."

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