An optically active amine A ( C ₅ H ₁₃ N ) gives a foul-smelling gas when heated with chloroform and alcoholic KOH . Compound A undergoes exhaustive methylation followed by heating with moist Ag ₂ O to yield an alkene B as the major product. Reductive ozonolysis of B yields formaldehyde and a branched-chain aliphatic aldehyde. The structure of amine A is:

Step-by-step solution

The positive carbylamine test (foul smell with CHCl ₃ and alcoholic KOH ) indicates that A is a primary amine. Compound A is optically active, meaning it must contain a chiral carbon atom. Exhaustive methylation followed by heating with moist Ag ₂ O (Hofmann elimination) yields the least substituted alkene as the major product (Hofmann rule). Reductive ozonolysis of B yields formaldehyde ( HCHO ), which confirms that B is a terminal alkene (contains a = CH ₂ group). The other product is a branched-chain aliphatic a