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Question #43970
The Question
An organic compound \textbf{X} () gives a positive Tollens' test and a positive iodoform test. A student attempts to perform a Cannizzaro reaction on \textbf{X} by treating it with 50% aqueous at , assuming the aldehyde group lacks -hydrogens. However, the reaction yields a single major aromatic product \textbf{Y} () instead of the expected disproportionation products. Which of the following represents the correct structure of \textbf{Y}?
Options
- A.
Naphthalen-2-ol
- B.
Naphthalen-1-ol
- C.
Equimolar mixture of 2-(2-oxopropyl)benzoic acid and 2-(2-oxopropyl)benzyl alcohol
- D.
3-Methyl-1H-inden-1-ol
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
Cannizzaro Mechanism|Alpha-Hydrogen Acidity|Aldol Condensation Directionality
Why This Question Is Tricky
Common Mistakes
This problem tests the competition between the Cannizzaro reaction and the Aldol condensation.
Students often blindly apply the heuristic 'no alpha-hydrogens on the aldehyde = Cannizzaro'.
The trap involves a 'hidden' acidic proton on a remote substituent (the methyl ketone) that shifts the reaction pathway entirely.
The formation of a resonance-stabilized enolate outcompetes the intermolecular hydroxide attack required for Cannizzaro, leading to an intramolecular cyclization and subsequent aromatization.
Quick Facts About This Question
Question Information
| Subject | Chemistry |
| Chapter | Aldehydes, Ketones, and Carboxylic Acids - Class 12 |
| Concept | Cannizzaro Mechanism |
| Difficulty | 8 |
| Cognitive Load | 7 |
| Target Solve Time | 160 sec |
| Access | Free |