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Question 55

The major product of the following reaction is:

Step 1: Reduction of the Nitrile with Ni/H2 Nickel with hydrogen gas (Ni/H2) is used to reduce the nitrile group selectively while leaving the ester group untouched.

  • The nitrile group (CN) gets fully reduced into a primary amine group (CH2-NH2).
  • Because there was already a CH2 group present, the side chain now becomes a CH2-CH2-NH2 chain.

Step 2: Ring Closure (Cyclization) The molecule now contains a nucleophilic amine group (NH2) and an electrophilic ester group (COOEt) right next to each other.

  • The nitrogen atom attacks the carbonyl carbon of the ester group.
  • The ethoxy group (OEt) leaves as ethanol.
  • This internal attack forms a stable 6-membered cyclic amide ring (a lactam) fused to the benzene ring.

Step 3: Reduction with DIBAL-H Diisobutylaluminum hydride (DIBAL-H) is a selective, bulky reducing agent. When it reacts with a cyclic amide (lactam), it reduces the carbonyl group (C=O).

  • The C=O bond is reduced, and subsequent elimination leads to the formation of a carbon-nitrogen double bond (C=N).

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