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Question #43955
The Question
Compound \textbf{X}, tert-butyl 2-formylbenzoate, is subjected to the following two-step reaction sequence: Identify the major products \textbf{Y} and \textbf{Z}.
Options
- A.
\textbf{Y} = tert-butyl 2-(hydroxymethyl)benzoate; \textbf{Z} = isobenzofuran-1(3H)-one
- B.
\textbf{Y} = isobenzofuran-1(3H)-one; \textbf{Z} = isobenzofuran-1(3H)-one
- C.
\textbf{Y} = tert-butyl 2-(hydroxymethyl)benzoate; \textbf{Z} = 2-(hydroxymethyl)benzoic acid
- D.
\textbf{Y} = 2-(hydroxymethyl)benzoic acid; \textbf{Z} = isobenzofuran-1(3H)-one
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
Reduction Selectivity (Hydrides)|Esterification Reversibility|Nucleophilic Acyl Substitution
Why This Question Is Tricky
Common Mistakes
The question tests the 'Steric Hindrance' exception in intramolecular nucleophilic acyl substitution.
Students often memorize that reduction of 2-formylbenzoates yields phthalides due to spontaneous in situ lactonization of the intermediate alkoxide.
The hidden variable is the steric bulk of the tert-butyl ester, which completely inhibits the mechanism, trapping the intermediate as the hydroxy ester.
The subsequent step tests the specific cleavage of tert-butyl esters by TFA, followed by acid-catalyzed lactonization, rewarding a deep mechanistic understanding over rote memorization.
Quick Facts About This Question
Question Information
| Subject | Chemistry |
| Chapter | Aldehydes, Ketones, and Carboxylic Acids - Class 12 |
| Concept | Reduction Selectivity (Hydrides) |
| Difficulty | 8 |
| Cognitive Load | 7 |
| Target Solve Time | 160 sec |
| Access | Free |