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JEE Main 202624 JanuaryMorning Shift
Exam
JEE Main
Year
2026
Date
24 January
Shift
Morning Shift
Subject
Chemistry
Chapter
Haloalkanes and Haloarenes

JEE Main 2026 · 24 January · Morning Shift · Chemistry · Haloalkanes and Haloarenes

Given below are two statements: Statement I : ' C-Cl^ bond is...

Given below are two statements:
Statement I: ' C−Cl′\mathrm{C}-\mathrm{Cl}^{\prime} bond is stronger in CH2=CH−Cl\mathrm{CH}_{2}=\mathrm{CH}-\mathrm{Cl} than CH3−CH2−Cl\mathrm{CH}_{3}-\mathrm{CH}_{2}-\mathrm{Cl}
Statement II: The given optically active molecule,
Given below are two statements: Statement I : ' C-Cl^ bond is stronger in CH_ 2 =CH-Cl than CH_ 3 -CH_ 2 -Cl Statement
on hydrolysis gives a solution that can rotate the plane polarized light.
In the light of the above statements, choose the correct answer from the options given below

Options

  1. AStatement I is false but Statement II is true
  2. BBoth Statement I and Statement II are true
  3. CBoth Statement I and Statement II are false
  4. DStatement I is true but Statement II is false

Correct answer

D. Statement I is true but Statement II is false

Step-by-step solution

Statement I: In vinyl chloride (CH₂=CH-Cl), the C-Cl bond involves an sp² hybridized carbon, while in ethyl chloride (CH₃-CH₂-Cl), it involves an sp³ carbon. The sp² carbon has greater s-character, forming a shorter and stronger C-Cl bond. Additionally, resonance stabilization from the Cl atom's p-orbital overlapping with the π system further strengthens the vinyl C-Cl bond. Statement I is TRUE.

Statement II: The optically active molecule shown has a stereogenic center bearing Me, Ph, Et, and Cl groups. Upon hydrolysis via nucleophilic substitution (typically SN1 for tertiary or secondary centers), the C-Cl bond breaks to form an alcohol. SN1 mechanism generates a carbocation intermediate, allowing nucleophilic attack from both faces, producing a racemic mixture of the alcohol product. A racemic solution cannot rotate polarized light as the d- and l-enantiomers cancel each other's rotations. Statement II is FALSE.
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