Question

Draw the major product(s) of nitration of benzenesulfonic acid. you do not have to consider stereochemistry. you do not have to explicitly draw h atoms. draw organic products only. separate multiple products using the + sign from the drop-down menu.

Answer 1

The nitration of benzenesulfonic acid would result in the substitution of a hydrogen atom on the benzene ring with a nitro group, leading to the formation of 2-nitrobenzenesulfonic acid or 4-nitrobenzenesulfonic acid, with the para (4-) position being more favored.

Step-by-step explanation:

The question concerns the nitration of benzenesulfonic acid, which is a chemical reaction that introduces a nitro group (-NO2) to an aromatic ring, in this case, benzene. Given that benzenesulfonic acid already has a sulfonic acid group (-SO3H), the nitration would typically occur at the position ortho or para to the existing substituent due to the directing effects of the sulfonic acid group. The major product of this nitration reaction would be a molecule with both -SO3H and -NO2 groups on the benzene ring. Specifically, you would expect to see benzenesulfonic acid turn into either 2-nitrobenzenesulfonic acid or 4-nitrobenzenesulfonic acid. The para position is often favored for steric reasons, so 4-nitrobenzenesulfonic acid might be the predominant product.

Answer 2

As we know Benzene undergo Electrophilic Substitution Reactions. In case of substituted Benzene the incoming Electrophile is substituted either at Orto , Para position or Meta position. If the substituent is Electron Withdrawing in Nature then the Electrophile will go to meta position. When the substituent id Electron Donating in Nature then the incoming electrophile will be directed to ortho and para position.

In Benzenesulfonic Acid the substituent is Sulfonate (-SO₃H), it has a strong electron withdrawing effect. So on Nitration the Nitro group will be oriented to meta position and 3-nitrobenzenesulfonic acid is formed. On further Nitration 3-nitrobenzenesulfonic acid will be convert to 3,5-dinitrobenzenesulfonic acid because both Sulfonate and Nitrate groups are meta directing.