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Addition Reactions of Benzyne

addition of NH3 to benzyne
addition of H2O to benzyne
Reaction type : elimination then addition

Summary

Related Reactions
MECHANISM OF THE ADDITION OF AMMONIA TO BENZYNE
Step 1:
The N in amide functions as the nucleophile and attacks the reactive triple bond C in benzyne creating the new C-N bond and an intermediate carbanion.
mechanism for the addition of ammonia to benzyne
Step 2:
An acid/base reaction. Rapid protonation of the reactive carbanion from the ammonia forms the aniline and anotheer molecule of the amide ion.

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organic chemistry © Dr. Ian Hunt, Department of Chemistry University of Calgary