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Question #44628

Difficulty: 8/10 | 🟢 Free

The Question

An alkyl halide XX (C5H11BrC_5H_{11}Br) is subjected to dehydrohalogenation under two different sets of conditions:

Reaction 1: X→NaOEt/EtOH, 350 KX \xrightarrow{NaOEt / EtOH, \ 350 \text{ K}} PP (Major) Reaction 2: X→KOtBu/t−BuOH, 350 KX \xrightarrow{KOtBu / t-BuOH, \ 350 \text{ K}} QQ (Major)

Reductive ozonolysis of PP yields a mixture of two carbonyl compounds; one gives both a positive Tollens' test and a positive iodoform test, while the other gives a negative Tollens' test. Reductive ozonolysis of QQ yields two carbonyl compounds, one of which is a gas at 298 K298 \text{ K} and the other gives a positive iodoform test.

What is the absolute difference in the number of hyperconjugative α\alpha-hydrogens between the major products PP and QQ?

Options

  • A.

    2

  • B.

    3

  • C.

    4

  • D.

    6

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

E1/E2 Solvent and Base Effects|E2 Regioselectivity (Saytzeff vs Hoffmann)

Why This Question Is Tricky

Common Mistakes

The question tests the E2 regioselectivity competition between thermodynamic (Saytzeff) and kinetic (Hoffmann) control.

Students often blindly apply Saytzeff's rule.

The 'hidden variable' is the steric bulk of the base (KOtBuKOtBu), which raises the activation energy for internal proton abstraction.

This forces the reaction to yield the anti-Saytzeff product.

The problem rigorously integrates qualitative organic analysis (Tollens'/Iodoform tests) to prevent guessing the substrate, ensuring a deep, multi-step mechanistic understanding.

Quick Facts About This Question

Question Information

SubjectChemistry
ChapterHaloalkanes and Haloarenes - Class 12
ConceptE1/E2 Solvent and Base Effects
Difficulty8
Cognitive Load7
Target Solve Time160 sec
AccessFree