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NCERT Class XII Chemistry
Chapter - Haloalkanes and Haloarenes
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Question : 9 of 31
Marks: +1, -0
Which compound in each of the following pairs will react faster in SN2 reaction with OH−^{-} ?
(i) CH3Br or CH3I\mathrm{CH}_3\mathrm{Br}\text{ or }\mathrm{CH}_3\mathrm{I}
(ii) (CH3)3CCl or CH3Cl(\mathrm{CH}_3)_3\mathrm{CCl}\text{ or }\mathrm{CH}_3\mathrm{Cl}
Solution:  
(i) Between CH3Br\mathrm{CH}_3\mathrm{Br} and CH3I\mathrm{CH}_3\mathrm{I}, CH3I\mathrm{CH}_3\mathrm{I} will react faster via the SN2\mathrm{S}_\mathrm{N}2 mechanism. In SN2\mathrm{S}_\mathrm{N}2 mechanism, C – X bond breaks and the faster it breaks faster is the reaction.
I−\mathrm{I}^{-} is a better leaving group. Owing to its large size, the C – I bond breaks faster than the C – Br bond and reaction proceeds further at a greater rate.
(ii) The order of reactivity in an SN2\mathrm{S}_\mathrm{N}2 reaction depends on minimal steric hindrance around the carbon involved in the C – X bond. Lesser the steric hindrance felt by the incoming nucleophile,more reactive will be the alkyl halide towards SN2\mathrm{S}_\mathrm{N}2 reaction.
Based on this, CH3Cl\mathrm{CH}_3\mathrm{Cl} will react faster than (CH3)3CCl(\mathrm{CH}_3)_3\mathrm{CCl}.
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