Treatment of tert-butyl alcohol with hydrogen chloride yields a mixture of tert-butyl chloride (SN1 product) and 2- methylpropene (E1 product). After chromatographic separation, how would you use 'H NMR to help you decide which was which?

Treatment of tert-butyl alcohol with hydrogen chloride yields a mixture of tert-butyl chloride (SN1 product) and 2- methylpropene (E1 product). After chromatographic separation, how would you use 'H NMR to help you decide which was which?

Macroscale and Microscale Organic Experiments

7th Edition

ISBN:9781305577190

Author:Kenneth L. Williamson, Katherine M. Masters

Publisher:Kenneth L. Williamson, Katherine M. Masters

Chapter43: Amines

Section: Chapter Questions

Problem 9Q

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Concept explainers

Analyzing and Predicting Spectroscopic Data

The interaction of electromagnetic radiation with the structure of molecules in the sample and their study is referred spectroscopy. Several spectroscopic methods are used to acquire sample information, and these methods are proved to be accurate, fast, and non-destructive. The information obtained about the content and composition of molecules from these spectroscopic methods is called spectroscopic data.

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Question 6

Treatment of tert-butyl alcohol with hydrogen chloride yields a mixture of tert-butyl chloride (SN1 product) and 2-
methylpropene (E1 product). After chromatographic separation, how would you use ¹H NMR to help you decide
which was which?

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