MEDIUMMCQ SINGLEJEE Mains ChemistryInorganic ChemistryAlkyl and Aryl HalidesSingle Choice Questions

The correct order of increasing reactivity of C – X bond towards nucleophile in the following compounds is (AIPMT 2010)

A.I < II < IV < III✓ Correct
B.II < III < I < IV
C.IV < III < I < II
D.III < II < I < IV
Explanation

The order of reactivity is dependent on the stability of the intermediate carbocation formed by cleavage of C– X bond. The 3o carbocation (formed from III) will be more stable than its 2o counterpart (formed from IV) which in turn will be more stable than the arenium ion (formed from I). Also, the aryl halide has a double bond character in the C–X bond which makes the cleavage more difficult. However, inspite of all the stated factors, II will be more reactive than I due to the presence of the electron withdrawing –NO2 group. C – X bond becomes weak and undergoes nucleophilic substitution reac

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