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Question #44418
The Question
Consider the organic compound , methyl 2-(2,4,6-tri-tert-butylphenyl)-2-oxoacetate. is treated with an excess of lithium aluminium hydride () in dry THF at , followed by a mild aqueous acidic workup to yield the major product . Identify the correct IUPAC name of .
Options
- A.
1-(2,4,6-tri-tert-butylphenyl)-2-hydroxyethan-1-one
- B.
1-(2,4,6-tri-tert-butylphenyl)ethane-1,2-diol
- C.
Methyl 2-hydroxy-2-(2,4,6-tri-tert-butylphenyl)acetate
- D.
2-(2,4,6-tri-tert-butylphenyl)ethan-1-ol
Check Your Answer
Correct Answer
Step-by-Step Solution
Explanation
How the Examiner Thinks
Exception_Exposure
Learn to identify edge cases and boundary exceptions that JEE examiners hide in math problems.
Concepts Behind This Question
Oxidation State Traps|Nucleophilic Addition Sterics|Reduction Selectivity (Hydrides)
Why This Question Is Tricky
Common Mistakes
This problem tests the boundary where severe steric hindrance completely overrides inherent electronic reactivity.
Students typically memorize the reactivity order (Aldehyde > Ketone > Ester) and assume an excess of a strong reducing agent like LiAlH4 will reduce all reducible functional groups to alcohols (yielding the diol).
The 'hidden variable' is the spatial impossibility of the transition state for the ketone reduction due to the massive ortho-tert-butyl groups.
This traps rote learners while rewarding those who evaluate 3D molecular geometry and steric protection.
Quick Facts About This Question
Question Information
| Subject | Chemistry |
| Chapter | Alcohols, Phenols, and Ethers - Class 12 |
| Concept | Oxidation State Traps |
| Difficulty | 8 |
| Cognitive Load | 7 |
| Target Solve Time | 160 sec |
| Access | Free |