KCET 2021 Chemistry Solved Paper

From the given information question, addition of HCl occured on A. That means A is an alkene.

C4H8

(A)

HCl

→

C4H9‌Cl

(B)

Cl in compound B is substituted by NH2 to give compound C(C4H11N).

C4H9‌Cl

(B)

NH3

→

C4H11N

(C)

C gives a diazonium salt with NaNO2∕HCl which on further treatment with water give an optically active alcohol. That means C is an aliphatic amine.
C

(i)NaNO2∕HCl

──────▶

(ii)H2O

D [Alcohol (optically active)]
From the given information it is concluded that the most probable structure of A is CH3−CH=CH−CH3.
As only but-2-ene gives optically active alcohol (D) as final product. The reactions involves are as follows.