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Haloalkanes and Haloarenes question

2010 · Q135
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Haloalkanes and Haloarenes question

2010 · Q135

NEETChemistryHaloalkanes and HaloarenesMCQ+4 / −1
The correct order of increasing reactivity of
AIPMT 2010 Prelims Chemistry - Haloalkanes and Haloarenes Question 21 English
C−-−X bond towards nucleophile in the following compounds is
  1. A
    I < II < IV < III
  2. B
    II < III < I < IV
  3. C
    IV < III < I < II
  4. D
    III < II < I < IV
View written solutionFree

Correct answer: A

The order of reactivity is dependent on the stability of the intermediate carbocation formed by cleavage of C—X bond. The 3° carbocation formed in III will be more stable than its 2° homologue (IV) which in turn will be more stable than arenium ion (I). Moreover, the aryl halide has a double bond character in the C—X bond which makes the cleavage more difficult. On other hand II will be more reactive than I due to presence of electron withdrawing —NO2 group. C—X bond becomes weak and undergoes nucleophilic substitution reaction

So Correct order is I < II < IV < III.

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