Why is m-nitro formed in the reaction of nitration of methyl benzoate instead of the ortho or...

Question:

Why is m-nitro formed in the reaction of nitration of methyl benzoate instead of the ortho or para isomers? Draw the structure of the products formed on nitration of each of the following compounds: benzene, phenol, and benzoic acid?

Substitution Reaction:

Substitution reactions occur in different ways. It can be through nitration, sulphonation, acylation and so on. In all these reactions, a group is transformed to another one by providing suitable reactants.

Answer and Explanation:


The nitration in methyl benzoate will give meta product. This is because the carboxylic group which is present in the functional group withdraws the electron density from the ring.

This makes it difficult for the electrophilic substitution as there will be not any negative charge formed in the ortho and para position.

The meta position is deactivated towards nitration.

Therefore, the nitration occurs in the meta position than ortho and para position.


The nitration in benzene occurs when concentrated sulphuric acid and nitric acid is supplied. The electrophile formed is nitronium ion and it gets substituted with the hydrogen atom from the ring. The reaction is shown in the picture below.


The nitration in phenol occurs when concentrated sulphuric acid and nitric acid is supplied. The electrophile formed is nitronium ion and it gets substituted with the hydrogen atom in the ortho or para position. The hydroxyl ion is ortho-para directing and thus the substitution occurs in ortho and para positions. The reaction is shown in the picture below.


The nitration in benzoic acid occurs when concentrated sulphuric acid and nitric acid is supplied. The electrophile formed is nitronium ion and it gets substituted with the hydrogen atom in the meta position. The carboxyl group is meta directing and thus the substitution occurs in meta position. The reaction is shown in the picture below.


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