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Question #44478
The Question
Consider the following multistep synthesis starting from Compound \textbf{X} (Methyl 7-((tetrahydro-2H-pyran-2-yl)oxy)hept-4-ynoate):
Identify the major product \textbf{P}.
Options
- A.
Cyclohept-4-en-1-one
- B.
Methyl (E)-7-deuterohept-4-enoate
- C.
Methyl (Z)-7-deuterohept-4-enoate
- D.
(E)-7-deuterohept-4-enoic acid
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
Lindlar vs. Birch Reduction|Grignard Reaction Pathways|Esterification Steric Hindrance
Why This Question Is Tricky
Common Mistakes
This question tests the intersection of stereoselective reduction and conformational constraints in ring formation.
Students often assume a 'flexible chain' and predict intramolecular Grignard cyclization to form a 7-membered ring (Option A).
However, they overlook that the Birch reduction strictly produces an (E)-alkene.
Forming a 7-membered ring with a trans double bond (trans-cycloheptene derivative) is geometrically impossible due to extreme ring strain.
The rigid geometry traps the Grignard reagent, forcing it to remain unreacted until the D_2O quench.
Quick Facts About This Question
Question Information
| Subject | Chemistry |
| Chapter | Hydrocarbons - Class 11 Part 2 |
| Concept | Lindlar vs. Birch Reduction |
| Difficulty | 8 |
| Cognitive Load | 7 |
| Target Solve Time | 160 sec |
| Access | Free |