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Question #44478

Difficulty: 8/10 | 🟢 Free

The Question

Consider the following multistep synthesis starting from Compound \textbf{X} (Methyl 7-((tetrahydro-2H-pyran-2-yl)oxy)hept-4-ynoate):

Compound X→2. Cat. p-TsOH, MeOH, 25∘C1. Na, NH3(l),−78∘CY\text{Compound \textbf{X}} \xrightarrow[2. \text{ Cat. } p\text{-TsOH, MeOH, } 25^\circ\text{C}]{1. \text{ Na, NH}_3(l), -78^\circ\text{C}} \textbf{Y}

Y→PBr3, pyridine, 0∘CZ\textbf{Y} \xrightarrow{PBr_3, \text{ pyridine, } 0^\circ\text{C}} \textbf{Z}

Z→2. Excess D2O1. Rieke Mg, THF, −78∘C, high dilutionMajor Product (P)\textbf{Z} \xrightarrow[2. \text{ Excess } D_2O]{1. \text{ Rieke Mg, THF, } -78^\circ\text{C, high dilution}} \textbf{Major Product (P)}

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

SubjectChemistry
ChapterHydrocarbons - Class 11 Part 2
ConceptLindlar vs. Birch Reduction
Difficulty8
Cognitive Load7
Target Solve Time160 sec
AccessFree