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- 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 bond
c) Longer bond
d) carbon bonded to , is more electronegative
Options
- Aa, b
- Bb, c
- Cb, d
- 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) carbon bonded to X is more electronegative: The carbon atom in an aryl halide is hybridized, which has more s-character ((33 \%)) than the hybridized carbon in an alkyl halide (25%). This makes the 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.