Question

The following sequence of reactions gives:

A.

B.

C.

D.

Answer 1

Hint: Amides are the compounds consisting of \[ - CON{H_2}\] functional group. Amides undergo Hoffmann bromination when treated with bromine in presence of sodium hydroxide to form primary amines. The primary amine and ester presence in the same molecule loses alcohol and undergoes cyclization.

Complete answer:
Given compound is a derivative of benzene. The substituents were ethanamide and methyl methanoate. These two groups were at ortho position to each other.
When the compound consisting of amide treated with bromine in presence of alkali like sodium hydroxide undergoes Hoffmann bromination to form primary amine. Thus, the amide group converts into a primary amine. The chemical reaction involved will be as follows:

The compound formed has primary amine and ester groups. When this compound is heated, it loses the methanol molecule, the methoxy group can be lost from the ester group and hydrogen from the amine group and forms a cyclized product.
The chemical reaction involved will be as follows:

Thus, the cyclic product will be a lactam. The cyclic amides are known as lactam.
The name of the product will be isoindolin- \[1\]-one. It belongs to the indole family as nitrogen is involved in a cyclic structure.
The final compound matches with the structure in option C.

Option C is the correct one.

Note:
Hoffmann bromination is an important organic reaction. It is one of the methods to prepare primary amines from amides. As primary amines are more basic and can easily lose a proton, whereas the ester loses the methoxy group. On heating, methanol will be eliminated.