Question

Draw the structure of the major nitration product from the reaction of nitric acid with 1,3-dimethylbenzene. Show all formal charges.

Answer 1

Concepts and reason

The concept that is used to solve the given problem is based on the process of nitration. The reactants 1,3-dimethylbenzene and nitric acid undergoes nitration in the presence of sulfuric acid to form the desired products. The methyl groups are basically the para and ortho directing groups.

Fundamentals

A group of chemical processes to introduce a nitro group into a chemical compound that is organic is termed as nitration. A major difference between the nitrates and newly formed structures of the nitro compound is the bonding of atoms.

The atom of nitrogen present in the nitro compounds is bonded directly to a non-oxygen atom either nitrogen or a carbon atom. However, in nitrates, the bonding of nitrogen occurs with an oxygen atom, which in turn shows bonding with.

There can be para and ortho methyl groups. The nitration occurs at the para position of a methyl group and ortho position of another methyl group. The reactants undergoing nitration can be treated with concentrated sulfuric acid to form nitrobenzene.

The two methyl groups participating in the process of nitration are para and methyl directing groups. Thus, nitration can occur at the ortho position of a methyl group as well as para position of another methyl group. This process of nitration forms 2,4-dimethyl-1- nitrobenzene, which can be shown in the following reaction:

Ans:

The major nitration product of 1,3-dimethylbenzene is 2,4-dimethyl-1-nitrobenzene.