Question

Identify the major product of the following reaction.

• A. 1
• B. 2
• C. 3
• D. 4

Hint:

Wolff--Kishner reduction: \[ R_2C=O \rightarrow R_2CH_2 \] uses hydrazine and strong base under heating conditions. It reduces aldehydes and ketones to hydrocarbons while leaving nitro groups generally unaffected.

Answer 1

The Correct Option is A

Step 1: Identify the reagents.
The reagents used are \[ N_2H_2,\ NaOH,\ \text{ethylene glycol},\ \Delta \] These are the conditions of the Wolff--Kishner reduction.
Wolff--Kishner reduction converts a carbonyl group \[ (\gt C=O) \] into a methylene group \[ (-CH_2-) \] without affecting the nitro group under these conditions.

Step 2: Examine the substrate.
The given compound contains: \[ -OH \] \[ -NO_2 \] and \[ -COCH_3 \] groups attached to the benzene ring.
The carbonyl-containing side chain is an acetyl group: \[ -COCH_3 \]

Step 3: Apply Wolff--Kishner reduction.
The acetyl group undergoes reduction: \[ Ar-COCH_3 \rightarrow Ar-CH_2CH_3 \] Thus, \[ -COCH_3 \] is converted into \[ -CH_2CH_3 \] The phenolic \(-OH\) group and nitro \(-NO_2\) group remain unchanged.

Step 4: Identify the product.
The resulting compound is 4-Ethyl-2-nitrophenol which corresponds to the first structure shown in the options.

Step 5: Final conclusion.
Therefore, the major product formed is \[ \boxed{\text{4-Ethyl-2-nitrophenol}} \] Hence, the correct option is \[ \boxed{(1)} \]