Question

Show how to convert toluene to 3 -hydroxybenzoic acid using the same set of reactions as in Example \(23.12\) but changing the order in which two or more of the steps are carried out.

Short answer

Short Answer Question: Using the same set of reactions as in Example 23.12, explain how to convert toluene into 3-hydroxybenzoic acid by modifying the order of the steps. Short Answer: To convert toluene into 3-hydroxybenzoic acid, we can follow these modified steps: 1. Mononitrate toluene to form o-nitrotoluene and p-nitrotoluene. 2. Reduce o-nitrotoluene to o-aminotoluene. 3. Perform hydrolysis on o-aminotoluene to form 3-hydroxybenzoic acid.

Step-by-step solution

Understanding the given reactions in Example 23.12.

In Example 23.12, we have the following set of reactions: a) Mononitration of toluene to form o-nitrotoluene and p-nitrotoluene. b) Reduction of o-nitrotoluene and p-nitrotoluene to o-aminotoluene and p-aminotoluene. c) Acetylation of o-aminotoluene and p-aminotoluene to form o-acetanilide and p-acetanilide. d) Hydrolysis of o-acetanilide and p-acetanilide to form o-hydroxybenzoic acid and p-hydroxybenzoic acid.

Modifying the order of reactions to obtain 3-hydroxybenzoic acid from toluene

To achieve the goal of converting toluene to 3-hydroxybenzoic acid, we need to change the order of the reactions. The new set of reactions is: 1. Mononitration of toluene to form o-nitrotoluene and p-nitrotoluene (same as in Example 23.12) 2. Reduction of o-nitrotoluene to o-aminotoluene (same as in Example 23.12) 3. Perform hydrolysis on o-aminotoluene to form 3-hydroxybenzoic acid.

Performing the reactions with modified order

1. Mononitration of toluene: Toluene + HNO3 -> o-nitrotoluene + p-nitrotoluene. 2. Reduction of o-nitrotoluene to o-aminotoluene: o-nitrotoluene + H2/Pd -> o-aminotoluene. 3. Hydrolysis of o-aminotoluene to form 3-hydroxybenzoic acid: o-aminotoluene + 2H2O + O2 -> 3-hydroxybenzoic acid + NH3. Now, we have successfully converted the toluene to 3-hydroxybenzoic acid using the same set of reactions as in Example 23.12, but changing the order of the reactions.