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Q. The alkyl halide that undergoes $ {{S}_{N}}1 $ reaction more readily is

KEAMKEAM 2009Haloalkanes and Haloarenes

Solution:

$ {{S}_{N}}1 $ mechanism involves formation of carbocation intermediate. Hence, the species which gives the most stable carbocation readily undergoes $ {{S}_{N}}1 $ mechanism, t-butyl bromide gives the most stable carbocation, ie, $ 3{}^\circ $ carbocation, so it readily undergoes $ {{S}_{N}}1 $ reaction.