JEE MainChemistryAlcohols Phenols and Ethers
Consider the following reaction sequence: 4-Methoxybenzaldehyde HNO ₃ / H ₂ SO ₄ A NH ₂ OH B [ ] SOCl ₂ C The major product 'C' is:
Options
- A4-Methoxy-3-nitrobenzonitrile
- B4-Methoxy-2-nitrobenzonitrile
- C4-Methoxy-3-nitrobenzamide
- D4-Hydroxy-3-nitrobenzonitrile
Correct answer
A. 4-Methoxy-3-nitrobenzonitrile
Step-by-step solution
In the first step, nitration of 4-methoxybenzaldehyde takes place. The methoxy group ( -OCH ₃ ) is activating and ortho/para directing, while the aldehyde group ( -CHO ) is deactivating and meta directing. Both groups synergistically direct the incoming electrophile ( NO ₂^+ ) to the position ortho to the methoxy group (which is meta to the aldehyde group). Thus, product A is 4-methoxy-3-nitrobenzaldehyde. In the second step, the aldehyde reacts with hydroxylamine ( NH ₂ OH ) to form an oxime (product B). In the fi