Salicylic acid on treatment with nitrating mixture produces

Options

A. Phenol
B. p-nitrosalicylic acid
C. Toluic acid
D. Benzoic acid

Answer

To determine the product formed when salicylic acid is treated with a nitrating mixture, we can follow these steps:

### Step 1: Identify the Structure of Salicylic Acid
Salicylic acid has the following structure:
- It contains a carboxylic acid group (-COOH) and a hydroxyl group (-OH) on a benzene ring.

### Step 2: Understand the Nitrating Mixture
The nitrating mixture consists of concentrated nitric acid (HNO3) and concentrated sulfuric acid (H2SO4). This mixture is used to introduce a nitro group (-NO2) into organic compounds.

### Step 3: Analyze the Directing Effects of the Functional Groups
In salicylic acid, the -COOH and -OH groups are both ortho/para directing groups:
- The -OH group is a strong activating group and directs electrophilic substitution to the ortho and para positions.
- The -COOH group is a deactivating group but still directs substitution to the ortho and para positions.

### Step 4: Determine the Positions for Nitration
Since the -OH group occupies one position on the benzene ring, the nitro group from the nitrating mixture will preferentially attach to the para position relative to the -OH group:
- The ortho position is blocked by the hydroxyl group, so the nitro group will go to the para position.

### Step 5: Draw the Product Structure
The product formed will have:
- The original -COOH group.
- The -OH group.
- A nitro group (-NO2) at the para position relative to the -OH group.

Thus, the final structure of the product is:
- **p-Nitrosalicylic acid**.

### Final Answer
When salicylic acid is treated with a nitrating mixture, it produces **p-Nitrosalicylic acid**.

---