(a) Give the products expected when acetic formic anhydride reacts with

(i) aniline and

(ii) benzyl alcohol

(b) Propose mechanisms for these reactions.

In this reaction, lone pair of electron of the nitrogen atom of aniline acts as a nucleophile, and it attacks the more electron deficient centre of the carbonyl carbon atom, i.e. aldehyde carbonyl

When acetic formic anhydride react with aniline then there is the formation of N-phenyl formamide and acetic acid as a side product,In this reaction nucleophilic substitution reaction take place.

In this reaction, lone pair of electron of oxygen atom of benzyl alcohol acts as a nucleophile and it attack to the more electron deficient centre of carbonyl carbon atom i.e. aldehyde carbonyl carbon.

When acetic formic anhydride reacts with aniline, then there is the formation of ester and acetic acid as a side product. Inthis reaction, a nucleophilic substitution reaction takes place.

In the first step of this reaction, lone pair of nitrogen atom attacks as a nucleophile and it attack the less hindered carbonyl carbon and there is a formation of intermediate product, In the second step negative charge on the oxygen atom, form a double bond with carbon and there is elimination of acetate ion.

In the last step acetate ion abstract the proton and neutralize the nitrogen atom and there is a formation of final product.

In the first step of this reaction, lone pair of oxygen atom attacks as a nucleophile and attack the less hindered carbonyl carbon, and there is a formation of an intermediate product. In the second step, the negative charge on the oxygen atom forms a double bond with carbon, and the acetate ion is eliminated.

In the last step, the acetate ion abstracts the proton and neutralizes the oxygen atom, and there is a formation of the final product.