Which compound in each of the following pairs will react faster in SN2 reaction with –OH?
(i)CH3Br or CH3I
(ii)(CH3)3CCl or CH3Cl
Which compound in each of the following pairs will react faster in SN2 reaction with –OH?
(i)CH3Br or CH3I
(ii)(CH3)3CCl or CH3Cl
Solution and Explanation
(i) In the SN2 mechanism, the reactivity of halides for the same alkyl group increases in the order.This happens because as the size increases,the halide ion becomes a better-leaving group.R−F<<R−Cl< R−Br<R−I Therefore,CH3I will react faster than CH3Br in SN2 reactions with OH−.
(ii)
The SN2 mechanism involves the attack of the nucleophile at the atom bearing the leaving group. But, in the case of (CH3)3CCl,the attack of the nucleophile at the carbon atom is hindered because of the presence of bulky substituents on that carbon atom bearing the leaving group. On the other hand, there are no bulky substituents on the carbon atom bearing the leaving group in CH3Cl.Hence,CH3Cl reacts faster than(CH3)3CCl in SN2 reaction with OH−.
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