Nitrous acid reacts with all classes of amines. The product obtained from these reactions depend on whether primary, secondary or tetriary and ,wheather the amine or aliphatic or aromatic.
Aliphalic primary amines react with acid `(NaNO_(2)+HCl)` to form alcohol as major product. In , addition to alcohol, alkene and alkyl halides are also formed as minor product.
Certain cyclic primary amines can undergo either ring expansion or ring contraction reactions on treatment with acid. This reaction is called Demajanov ring expansion or contraction.

Which of the following product(s) will be obtained when isopropylamine is treated with sodium nitrite and hydrochloric acid?

Options

A. `CH_(3)-underset(OH)underset(|)(CH)-CH_(3)`
B. `CH_(3)-CH=CH_(2)`
C. `CH_(3)-overset(Cl)overset(|)(CH)-CH_(3)`
D. all of these

Answer

D