2 - Methyl propyl bromide reacts with C 2 H 5 O - and gives ‘ A ’ whereas on reaction with C 2 H…

2-Methyl propyl bromide reacts with C2H5O-and gives A whereas on reaction with C2H5OH it gives B. The mechanism followed in these reactions and the products A and B respectively are:

  1. SN2,A=iso-butyl ethyl ether;SN1,B=tert-butyl ethyl ether

  2. SN1, A=tert-butyl ethyl ether; SN1, B=2-butyl ethyl ether

  3. SN2, A=2-butyl ethyl ether; SN2, B=iso-butyl ethyl ether

  4. SN1, A=tert-butyl ethyl ether; SN2, B=iso-butyl ethyl ether

Solution

The reaction between methyl propyl bromide and C2H5O- proceeds via an SN2 (substitution nucleophilic bimolecular) mechanism. In this mechanism, the nucleophile attacks the carbon atom bearing the bromine (the electrophilic carbon) in a single step, leading to the displacement of the bromine atom.

The reaction between methyl propyl bromide and C2H5OH can proceed via either an SN1 (substitution nucleophilic unimolecular). Here C2H5OH is a weak nucleophile. During the reaction 1,2-hydrogen shift will occur and tert-butyl ethyl ether is formed.

Asked in: JEE Main 2023 (13 Apr Shift 1)

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