Fundamentals of Organic ChemistryChemistryAldehydes and Ketones
Identify the major product C in the following reaction sequence:
Correct answer
3
Step-by-step solution
The given reaction sequence involves the Tiffeneau-Demjanov rearrangement. The starting material, 5-methylindan-1-one, reacts with hydrogen cyanide (HCN). This is a nucleophilic addition reaction at the carbonyl group, which forms a cyanohydrin. The product A is 1-cyano-5-methylindan-1-ol. The cyanohydrin A is reduced using lithium aluminum hydride ( LiAlH ₄ ) followed by hydrolysis. LiAlH ₄ reduces the cyano group ( -CN ) to a primary amine ( -CH ₂ NH ₂ ). The product B is 1-(aminomethyl)-5-methylindan-1-ol. Produ