Answered: How you can use the 1H NMR spectrum to…

How you can use the 1H NMR spectrum to establish if Product A or Product B was formed in this reaction? Explain your reasoning.

Introduction to General, Organic and Biochemistry

11th Edition

ISBN:9781285869759

Author:Frederick A. Bettelheim, William H. Brown, Mary K. Campbell, Shawn O. Farrell, Omar Torres

Publisher:Frederick A. Bettelheim, William H. Brown, Mary K. Campbell, Shawn O. Farrell, Omar Torres

Chapter16: Amines

Section: Chapter Questions

Problem 16.39P

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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.

Question

take a look at this reaction (first image)

The second image shows the ¹H NMR spectrum of the compound that was isolated as only product of this reaction:

How you can use the ¹H NMR spectrum to establish if Product A or Product B was formed in this reaction? Explain your reasoning.

2-Acetnaphthone
NaBH4
CH3OH
Product A
OH
or
Product B
?

8
9
4
2
0 [ppm]
4.0
3.0
1.0
3.0
- 2
0
2 4
6
8 10
[rel]

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Step 1: Interpretation of problem statement

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Step 2: NMR Signals for Product A and Product B

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Step 3: Identification of the product using NMR

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Analyzing and Predicting Spectroscopic Data

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