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JEE Advanced2023Paper 1CHEM-III
Q.

The total number of sp hybridised carbon atoms in the major product P (a non-heterocyclic compound) of the following reaction is _______.

Solution

Step (i): exhaustive nitrile reduction. Excess LiAlH reduces each of the four nitrile groups to a primary amine. The intermediate is the tetraamine .

Step (ii): condensation with acetophenone. Each primary amine reacts with one molecule of acetophenone (PhCOCH) to form an imine (Schiff base) with loss of water: . Four imines form, one for each amine.

Counting sp carbons in P. Each of the four imine units contributes: (i) one imine carbon , sp, and (ii) one phenyl ring with six sp carbons. The methyl carbon attached to the imine is sp and is not counted. Per unit: sp carbons. Total for four units: .

The central two CH carbons and the four CH carbons of the aliphatic backbone are sp and contribute zero.

Answer: 28.

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