Question:
Which one of the following compounds does not give benzoic acid when treated with alkaline \( KMnO_4 \)?
Which one of the following compounds does not give benzoic acid when treated with alkaline \( KMnO_4 \)?
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Oxidation by \( KMnO_4 \) requires at least one benzylic hydrogen for conversion to benzoic acid.
Updated On: Jun 5, 2025
- Acetophenone
- n-Propyl benzene
- Styrene
- t-Butyl benzene
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Verified By Collegedunia
The Correct Option is D
Solution and Explanation
Step 1: Understanding Oxidation by \( KMnO_4 \)
Potassium permanganate oxidizes benzylic positions to carboxyl groups if there is at least one hydrogen at the benzylic carbon.
Step 2: Evaluating Each Compound
- Acetophenone (\( C_6H_5COCH_3 \)) → Ketones do not undergo oxidation to benzoic acid, but side chains like methyl (–CH\(_3\)) do.
- n-Propyl benzene (\( C_6H_5CH_2CH_2CH_3 \)) → Converts to benzoic acid.
- Styrene (\( C_6H_5CH=CH_2 \)) → Oxidation leads to benzoic acid.
- t-Butyl benzene (\( C_6H_5C(CH_3)_3 \)) → No benzylic hydrogen, thus does not undergo oxidation.
Conclusion
Thus, the correct answer is:
\[
t\text{-Butyl benzene}
\]
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