Identify the major product of the following reaction sequence: CH ₃ COOH (i) SOCl ₂ (ii) 3-Methylaniline (iii) LiAlH ₄ , then H ₃ O ⁺ ?

Step-by-step solution

Reaction of acetic acid with thionyl chloride ( SOCl ₂ ) yields acetyl chloride. CH ₃ COOH SOCl ₂ CH ₃ COCl + SO ₂ + HCl Acetyl chloride reacts with 3-methylaniline (nucleophilic acyl substitution) to form an amide, N-(3-methylphenyl)acetamide. CH ₃ COCl + H ₂ N - C ₆ H ₄- CH ₃ CH ₃ CONH - C ₆ H ₄- CH ₃ + HCl Reduction of the amide with lithium aluminium hydride ( LiAlH ₄ ) followed by acidic workup converts the carbonyl group ( - C = O ) to a methylene group ( - CH ₂- ), yielding a secondary amine, N-ethyl-3-methy