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Question

Arrange the compounds of each set in order of reactivity towards SN2 displacement.
(i) 2-Bromo-2-methylbutane, 1-Bromopentane, 2-Bromopentane

(ii) 1-Bromo-3-methylbutane, 2-Bromo-2-methylbutane, 2-Bromo-3-methylbutane

(iii) 1-Bromobutane, 1-Bromo-2, 2-dimethylpropane, 1-Bromo-2-methylbutane,1-Bromo-3-methylbutane.

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Solution

In SN2 reaction, steric factors determine the reactivity. more reactive alkyl halides have less steric hinderance. Hence, the decreasing order of the reactivity of alkyl halides is 1o>2o>3o.
(i) 1-Bromopentane > 2-Bromopentane > 2-Bromo-2-methylbutane
(ii) 1-Bromo-3-methylbutane > 2-Bromo-3-methylbutane > 2-Bromo-2-methylbutane
(iii) 1-Bromobutane > 1-Bromo-3-methylbutane > 1-Bromo-2-methylbutane > 1-Bromo-2, 2-dimethylpropane

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