Haloalkanes and Haloarenes

Question

Which would undergo SN1 reaction faster in the following pair?

Answer

A tertiary alkyl halide tends to undergo the SN1 mechanism because it can form a tertiary carbocation, which is stabilized by the three alkyl groups attached to it. As alkyl groups are electron donating, they allow the positive charge in the carbocation to be delocalized by the induction effect. Hence, out of the given pairs, (CH3)3C-Br would undergo SN1 reaction faster than CH3-CH2-Br.

Order of stability:  tertiary>secondary>primary

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