From the given information question, addition of
HCl occured on A. That means A is an alkene.
Cl in compound B is substituted by
NH2 to give compound
C(C4H11N).
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.