Q. 16 C3.9( 7 Votes )

Arrange the compounds of each set in order of reactivity towards SN2 displacement:

1-Bromobutane, 1-Bromo-2,2 dimethylpropane, 1-Bromo-2-methylbutane, 1-Bromo-3-methylbutane.

Answer :

The stearic hinderance to the nucleophile in the SN2 mechanism increases with a decrease in the distance of the substituents from the atom containing the leaving group. Further, the stearic hinderance increases with an increase in the number of substituents. Therefore, the

increasing order of steric hindrances in the given compounds is as below:

1-Bromobutane < 1-Bromo-3-methylbutane < 1-Bromo-2-methylbutane < 1-Bromo-2, 2-dimethylpropane

The structures are given below:

Hence, the increasing order of reactivity of the given compounds towards SN2 displacement

1-Bromo-2, 2-dimethylpropane < 1-Bromo-2-methylbutane < 1-Bromo-3- methylbutane < 1-Bromobutane

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