Identify the major product formed in the following reaction sequence: (i) HCN (ii) LiAlH ₄ (iii) NaNO ₂, HCl

Step-by-step solution

The reaction of 1-indanone with HCN undergoes nucleophilic addition to form a cyanohydrin, 1-hydroxy-1-cyanoindane. Subsequent reduction with LiAlH₄ converts the cyano group ( - CN ) into a primary amine ( - CH₂NH₂ ), producing 1-(aminomethyl)indan-1-ol. Reaction with NaNO₂ and HCl leads to diazotization of the primary amine. The aliphatic diazonium ion readily loses N₂ to generate a primary carbocation at the exocyclic carbon ( - CH₂^+ ). This species undergoes a Tiffeneau-Demjanov ring expansion. Due to the highe