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Question

Consider the following pair of compounds:

(i) 1-bromo-2-methylpropane or 3-bromopentane

(ii) 2-chloropentane or 1-chloro-3-methylbutane

(iii) 1-fluoro-2-methylbutane or 2-fluoro-3-methylbutane

Identify the better S_N2 substrate.

Accepted Answer

(i) 1-bromo-2-methylpropane

(ii) 1-chloro-3-methylbutane

(iii) 1-fluoro-2-methylbutane

Answer

(i) 3-bromopentane