When chlorobenzene isotopically labeled with specifically at the carbon is reacted with in liquid ammonia, the resulting aniline product is a mixture of -substituted and adjacent-carbon substituted an

Question

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

Prashant Kotian · Accepted Answer

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

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