In attempting to make 2–bromo–2–methyl–propane from 2–methyl-propene, as shown below, you used a dilute aqueous solution of hydrobromic acid. Upon analysis of the isolated product, you realize there is a major unwanted by-product. Br a) Based on the reaction conditions used, predict the major by-product and show a mechanism for its formation. b) What should be changed in the reaction conditions described in order to completely avoid the formation of the unwanted by-product?

In attempting to make 2–bromo–2–methyl–propane from 2–methyl-propene, as shown below, you used a dilute aqueous solution of hydrobromic acid. Upon analysis of the isolated product, you realize there is a major unwanted by-product. Br a) Based on the reaction conditions used, predict the major by-product and show a mechanism for its formation. b) What should be changed in the reaction conditions described in order to completely avoid the formation of the unwanted by-product?

Organic Chemistry

9th Edition

ISBN:9781305080485

Author:John E. McMurry

Publisher:John E. McMurry

Chapter17: Alcohols And Phenols

Section17.SE: Something Extra

Problem 71AP: A problem often encountered in the oxidation of primary alcohols to acids is that esters are...

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