10.9 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
(i) In the S2 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, CHI will react faster than CHBr in S2 reactions with OH−. (ii)
The S2 mechanism involves the attack of the nucleophile at the atom bearing the leaving
group. But, in case of (CH)CCl, 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 CHCl. Hence, CHCl reacts faster than (CH)CCl in S2
reaction with OH.
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