When chlorobenzene isotopically labeled with 14C specifically at the C-Cl carbon is reacted with in liquid ammonia, the resulting aniline product is a 50:50 mixture of 14C-substituted and adjacent-car

Question

When chlorobenzene isotopically labeled with 14C specifically at the C-Cl carbon is reacted with $NaNH_2$ in liquid ammonia, the resulting aniline product is a 50:50 mixture of 14C-substituted and adjacent-carbon substituted anilines. This cine-substitution perfectly proves the existence of:

Prashant Kotian · Accepted Answer

Correct answer: A. The benzyne intermediate has a completely symmetrical "triple bond." The incoming nucleophile (NH2-) can attack either carbon of this strained bond with equal probability, leading to direct and cine-substitution.

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