Draw the structure of the aromatic product from the following reaction

Expert Solution

Concepts and reason

An acid anhydride reacts with amines to form an amide bond. Amide bond consists of CONH group, in which $\mathrm{NH}$ group acts as a nucleophile and $\mathrm{CO}$ group acts as an electrophile.

Fundamentals

Acid anhydrides are the compounds that are produced by removing water molecules from the acid and these act as nucleophiles. When an acid anhydride reacts with an amine, it forms a peptide bond.

The given substrate is shown below.

The given substrate consists of two functional groups namely $\mathrm{OH}$ and $\mathrm{NH}_{2}$. The amine group $\left(\mathrm{NH}_{2}\right)$ is more nucleophilic than $\mathrm{OH}$ since the electron density around $\mathrm{NH}_{2}$ is more than $\mathrm{OH}$.

The reaction can be written as follows.

The structure of the aromatic product is

The amine group is more nucleophilic than $\mathrm{OH}$ group. Hydrogen can be removed from amine $\left(\mathrm{NH}_{2}\right)$ group thereby electrophilic attack of anhydride takes place resulting in the formation of the peptide bond.

The structure of the aromatic product is

Dr. OWL answered 3 years ago

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