1.

Which compound in each of the following pairs will react faster in S_(N)2 reaction with OH^(-)? (a) CH_(3)Br or CH_(3)I (b) CH_(2)=CHBr or CH_(2)=CHCH_(2)Br.

Answer»

Solution :(a) Since `I^(-)` ion is a better leaving group than `Br^(-)` ion, therefore, iodidies are more reactive than bromides. In other words, `CH_(3)I` is more reactive than `CH_(3)Br`.
(b) Reactiviity in `S_(N)2` reactions among other things DEPENDS upon the magnitude of the +ve charge on the carbon atom carrying the halogen. now the `sp^(2)`-carbon atom of the `CH_(2)` group carrrying the Br atom in `CH_(2)=CHCH_(2)Br` carries more +ve charge due to -I-effect of the Br atom and the `CH_(2)=CH`- group as COMPARED to `sp^(2)`-carbon atom of `CH` group in `CH_(2)=CHBr` due to electron-donating RESONANCE effect.

As a result, `CH_(2)=CHCH_(2)Br` will react faster than `CH_(2)=CHBr` with `OH^(-)` ions.


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