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NEET
Exam
NEET
Subject
Chemistry
Chapter
Haloalkanes and Haloarenes

NEET · Chemistry · Haloalkanes and Haloarenes

Which of the following reasons support that arylhalides are less...

Which of the following reasons support that arylhalides are less reactive than alkyl halides towards nucleophilic substitution reactions? a) The formation of more stable arenium ion b) Partial double bond character of C−X\mathrm{C}-\mathrm{X} bond c) Longer C−X\mathrm{C}-\mathrm{X} bond d) sp2\mathrm{sp}^2 carbon bonded to X\mathrm{X}, is more electronegative

Options

  1. Aa, b
  2. Bb, c
  3. Cb, d
  4. Da, d

Correct answer

C. b, d

Step-by-step solution

The correct reasons why aryl halides are less reactive than alkyl halides towards nucleophilic substitution are (\mathrm{b}) and (\mathrm{d}). - b) Partial double bond character of C-X bond: Due to resonance, the lone pair on the halogen atom is delocalized into the benzene ring, creating a partial double bond character between the carbon and the halogen. This makes the C-X bond shorter and stronger than in an alkyl halide, thus harder to break. - d) sp2s p^2 carbon bonded to X is more electronegative: The carbon atom in an aryl halide is sp2s p^2 hybridized, which has more s-character ((33 \%)) than the sp3s p^3 hybridized carbon in an alkyl halide (25%). This makes the sp2s p^2 carbon more electronegative and able to hold the shared electron pair more tightly. Consequently, the carbon-halogen bond is stronger and less susceptible to nucleophilic attack.
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