Action of benzoic acid with hydroazoic acid in presence of conc. `H_(2)SO_(4)` followed by hydrolysis:

Options

A. Aniline
B. Benzamide
C. Phenyl cyanide
D. All

Explanation

To solve the problem of the action of benzoic acid with hydroazoic acid in the presence of concentrated sulfuric acid followed by hydrolysis, we can break it down into a series of steps:

### Step 1: Reactants and Initial Setup
We start with benzoic acid (C₆H₅COOH) and hydroazoic acid (HN₃) in the presence of concentrated sulfuric acid (H₂SO₄). The sulfuric acid acts as a catalyst and protonates the benzoic acid, making it more reactive.

**Hint:** Identify the reactants and their roles in the reaction.

### Step 2: Protonation of Benzoic Acid
The lone pair of electrons on the oxygen atom of the carboxylic acid group in benzoic acid attacks a proton (H⁺) from sulfuric acid, resulting in the formation of a positively charged benzoic acid derivative.

**Hint:** Look for the role of sulfuric acid in protonating the reactants.

### Step 3: Formation of a Reactive Intermediate
The protonated benzoic acid undergoes intramolecular proton transfer, which leads to the formation of a good leaving group (water) and a positively charged carbonyl compound.

**Hint:** Consider how intramolecular proton transfer can stabilize the intermediate.

### Step 4: Nucleophilic Attack by Hydroazoic Acid
The negatively charged nitrogen from hydroazoic acid (N₃⁻) attacks the carbonyl carbon of the reactive intermediate, forming a new compound that contains a nitrogen group.

**Hint:** Focus on the nucleophilic nature of hydroazoic acid and its attack on the carbonyl carbon.

### Step 5: Rearrangement and Loss of Nitrogen Gas
The newly formed compound undergoes rearrangement, resulting in the loss of nitrogen gas (N₂) and the formation of an intermediate that is positively charged.

**Hint:** Identify the significance of nitrogen gas leaving the reaction.

### Step 6: Hydrolysis
Water (from hydrolysis) attacks the positively charged carbon, leading to the formation of an amine and a carboxylic acid. The carboxylic acid can then deprotonate to yield the final product.

**Hint:** Recognize the role of water in hydrolysis and how it contributes to the final product.

### Step 7: Final Product
The final product of this reaction is aniline (C₆H₅NH₂) along with carbon dioxide (CO₂) as a byproduct.

**Hint:** Determine the final product by considering the structure of the reactants and the transformations that occurred.

### Conclusion
The overall reaction can be summarized as:
\[ \text{C}_6\text{H}_5\text{COOH} + \text{HN}_3 \xrightarrow{\text{H}_2\text{SO}_4} \text{C}_6\text{H}_5\text{NH}_2 + \text{CO}_2 \]

Thus, the product of the action of benzoic acid with hydroazoic acid in the presence of concentrated sulfuric acid followed by hydrolysis is **aniline**.