Discussion
The major product formed in the following reaction is
- A.
- B.
- C.
- D.
Answer: C
The product is (C), indane-1-carbonitrile.
Sodium amide in liquid ammonia removes HCl from the aryl chloride through a benzyne intermediate. The strong base also removes a proton from the carbon next to the nitrile (the acidic CH2 that bears CN). That carbanion sits three carbons from the ring and attacks the benzyne carbon next to the chain, closing a five-membered ring. Protonation then gives the bicyclic nitrile with CN on the carbon of the new ring.
(A) and (B) are the products of amide ion adding to the benzyne, which loses to the faster intramolecular carbanion attack. (D) is a ketone, and no step in the sequence converts a nitrile into a ketone.
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