Aldehydes, Ketones and Carboxylic Acids

Aldehydes, Ketones and Carboxylic Acids

Question

Rearrange the compounds of each of the following sets 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, 3-Bromo-2-methylbutane

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

Answer

(i) 1-Bromopentane > 2-Bromopentane > 2-Bromo-2-methylbutane

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

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

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