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Question #44009
The Question
Compound , 2-(2-oxopropyl)benzaldehyde, is treated with Tollens' reagent ( in aqueous ) at . Instead of the expected oxidation to a carboxylic acid and the formation of a silver mirror, undergoes a rapid base-catalyzed intramolecular reaction driven by a strong thermodynamic force, completely bypassing the oxidation pathway. Identify the major organic product isolated from this reaction.
Options
- A.
2-Naphthol
- B.
2-(2-Oxopropyl)benzoic acid
- C.
3-Methyl-1H-inden-1-ol
- D.
1,4-Naphthoquinone
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
Tollens vs. Fehling Specificity|Enolate Regioselectivity|Alpha-Hydrogen Acidity
Why This Question Is Tricky
Common Mistakes
This question tests the 'Hidden Variable' of the basicity of Tollens' reagent and the competition between Kinetic and Thermodynamic control in polyfunctional molecules.
Students typically memorize Tollens' reagent strictly as an aldehyde oxidant.
However, in molecules where a base-catalyzed intramolecular reaction can lead to a highly stable aromatic system, the Aldol condensation outcompetes the oxidation.
The trap also tests regioselectivity: students might erroneously form a 5-membered indene ring by miscounting atoms or assuming the more acidic benzylic protons dictate the nucleophilic attack, ignoring the geometric impossibility of forming a 4-membered ring from the ortho position.
Quick Facts About This Question
Question Information
| Subject | Chemistry |
| Chapter | Aldehydes, Ketones, and Carboxylic Acids - Class 12 |
| Concept | Tollens vs. Fehling Specificity |
| Difficulty | 8 |
| Cognitive Load | 7 |
| Target Solve Time | 160 sec |
| Access | Free |