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Question #43960
The Question
Consider the reaction of 1-(benzyloxy)propan-2-one under standard Clemmensen reduction conditions:
Identify the major organic product(s) formed in this reaction.
Options
- A.
\ce{Ph-CH2-O-CH2-CH2-CH3}
- B.
\ce{Ph-CH2-Cl} + \ce{CH3-CH2-CH2-OH}
- C.
\ce{Ph-CH3} + \ce{CH3-CH2-CH2-OH}
- D.
\ce{Ph-CH2-OH} + \ce{CH3-CH2-CH2-Cl}
Check Your Answer
Correct Answer
Step-by-Step Solution
Explanation
How the Examiner Thinks
Mechanism_Trap
Don't get tricked by the process! Learn the mechanical traps used in competitive exam questions.
Concepts Behind This Question
Clemmensen vs. Wolff-Kishner|Ether Cleavage Patterns
Why This Question Is Tricky
Common Mistakes
Students often treat named reactions as isolated functional group transformations, assuming Clemmensen reduction only affects the carbonyl group.
The 'Hidden Variable' here is the strongly acidic and thermal reaction condition, which is incompatible with acid-sensitive groups like benzylic ethers (unlike the basic Wolff-Kishner reduction).
The problem tests two layers of understanding: (1) Recognizing the ether cleavage side-reaction, and (2) Determining the correct regioselectivity of this cleavage.
The benzylic C-O bond is cleaved preferentially over the aliphatic C-O bond due to the stability of the benzylic transition state, trapping students who might choose the wrong cleavage products or assume the ether remains intact.
Quick Facts About This Question
Question Information
| Subject | Chemistry |
| Chapter | Aldehydes, Ketones, and Carboxylic Acids - Class 12 |
| Concept | Clemmensen vs. Wolff-Kishner |
| Difficulty | 8 |
| Cognitive Load | 7 |
| Target Solve Time | 160 sec |
| Access | Free |