a) Sketch the energy diagram for the conversion of tertiary butyl bromide to methyl t-butyl ether. Note that this is a two step reaction with the t-butyl cation as an intermediate. Assume that this is overall an exothermic reaction. Show the location of both transition states and the intermediate. The first step has the higher energy of activation and is the rate determining step. (CH3)3C-Br ------> (CH3)3C+ + Br- (CH3)3C+ + H3CO- ------> (CH3)3C-O-CH3 (b)Draw the curved arrow mechanism and the transition state when the tertiary butyl carbocation reacts with the methoxide ion to give an ether. (CH3)3C+ + H3CO- ------> (CH3)3C-O-CH3

a) Sketch the energy diagram for the conversion of tertiary butyl bromide to methyl t-butyl ether. Note that this is a two step reaction with the t-butyl cation as an intermediate. Assume that this is overall an exothermic reaction. Show the location of both transition states and the intermediate. The first step has the higher energy of activation and is the rate determining step. (CH3)3C-Br ------> (CH3)3C+ + Br- (CH3)3C+ + H3CO- ------> (CH3)3C-O-CH3 (b)Draw the curved arrow mechanism and the transition state when the tertiary butyl carbocation reacts with the methoxide ion to give an ether. (CH3)3C+ + H3CO- ------> (CH3)3C-O-CH3

Organic Chemistry: A Guided Inquiry

2nd Edition

ISBN:9780618974122

Author:Andrei Straumanis

Publisher:Andrei Straumanis

Chapter14: Elimination

Section: Chapter Questions

Problem 41CTQ

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