Question

Nitration of the compound is carried out. This compound gives red-orange precipitate with 2,4-DNP, undergoes Cannizzaro reaction but not aldol, then the possible product due to nitration is:

• A. \( \text{3-nitroacetophenone} \)
• B. \( \text{(2-nitro)-2-phenylethanol} \)
• C. \( \text{(2-nitro)-1-phenylpropan-2-one} \)
• D. \( \text{3-nitrobenzaldehyde} \)

Hint:

Aldehydes without alpha-hydrogens undergo Cannizzaro reactions, leading to no aldol condensation. The electron-withdrawing nature of the \( \text{-CHO} \) group directs electrophilic substitution to the meta-position.

Answer 1

The Correct Option is D

The compound, exhibiting a Cannizzaro reaction but lacking aldol condensation, is devoid of alpha-hydrogens. This characteristic points to it being an aldehyde. When subjected to nitration, benzaldehyde yields \( \text{3-nitrobenzaldehyde} \).Step 1: Reaction mechanism. \[\text{CHO} \xrightarrow{\text{Nitration}} \text{NO}_2\text{-CHO}.\] The aldehyde group, \( \text{-CHO} \), is electron-withdrawing, directing nitration to the meta-position. Conclusion: The resultant product is \( \boxed{\text{3-nitrobenzaldehyde}} \).