ORGANIC CHEMISTRY W/BIOLOGICAL TOPICS
ORGANIC CHEMISTRY W/BIOLOGICAL TOPICS
6th Edition
ISBN: 9781260325294
Author: SMITH
Publisher: RENT MCG
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Chapter 12C, Problem 36P

(a) How many 1 H NMR signals does each of the following compounds exhibit? (b) How many 13 C NMR

signals does each of the following compounds exhibit?

Chapter 12C, Problem 36P, 14.34 (a) How many  NMR signals does each of the following compounds exhibit? (b) How many  NMR

Expert Solution
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Interpretation Introduction

(a)

Interpretation: The number of 1H NMR signals present in each of the given compounds is to be identified.

Concept introduction: The number of NMR signal in a compound is equal to the number of chemically non-equivalent protons present in that compound. In 1HNMR all chemically equivalent protons generates one signal or one peak, whereas non-equivalent proton generates different signals.

Answer to Problem 36P

The given compound A gives four signals and compound B gives five signals in 1H NMR spectrum.

Explanation of Solution

The given compound A is the ball and stick model of 2(chloromethoxy)1methoxy2methylpropane. The bond-line representation of the compound A with all chemically non-equivalent protons is shown below.

ORGANIC CHEMISTRY W/BIOLOGICAL TOPICS, Chapter 12C, Problem 36P , additional homework tip  1

Figure 1

There are four non-equivalent protons (Ha, Hb, Hc and Hd) present in compound A. The number of signals in each compound is equal to the number of hydrogen atoms present in a different chemical environment. Therefore, the compound A gives four signals in 1H NMR spectrum.

The given compound B is the ball and stick model of propyl butyrate. The bond-line representation of the compound B with all chemically non-equivalent protons is shown below.

ORGANIC CHEMISTRY W/BIOLOGICAL TOPICS, Chapter 12C, Problem 36P , additional homework tip  2

Figure 2

There are five non-equivalent protons (Ha, Hb, Hc, Hd and He) present in compound B. The number of signals in each compound is equal to the number of hydrogen atoms present in a different chemical environment. Therefore, the compound B gives five signals in 1H NMR spectrum.

Conclusion

The given compound A gives four signals and compound B gives five signals in 1H NMR spectrum.

Expert Solution
Check Mark
Interpretation Introduction

(b)

Interpretation: The number of 13C NMR signals present in each of the given compounds is to be identified.

Concept introduction: The number of NMR signal in a compound is equal to the number of carbon atoms present in that compound. In 13C NMR all chemically equivalent carbon atoms generates one signal or one peak, whereas non-equivalent carbon atoms generates different signals.

Answer to Problem 36P

The given compound A gives five signals and compound B gives six signals in 13C NMR spectrum.

Explanation of Solution

The given compound A is the ball and stick model of 2(chloromethoxy)1methoxy2methylpropane. The bond-line representation of the compound A with all chemically non-equivalent carbon atoms is shown below.

ORGANIC CHEMISTRY W/BIOLOGICAL TOPICS, Chapter 12C, Problem 36P , additional homework tip  3

Figure 3

There are five non-equivalent carbon atoms (Ca, Cb, Cc, Cc and Ce) present in compound A. The number of signals in each compound is equal to the number of carbon atoms present in a different chemical environment. Therefore, the compound A gives five signals in 13C NMR spectrum.

The given compound B is the ball and stick model of propyl butyrate. The bond-line representation of the compound B with all chemically non-equivalent carbon atoms is shown below.

ORGANIC CHEMISTRY W/BIOLOGICAL TOPICS, Chapter 12C, Problem 36P , additional homework tip  4

Figure 4

There are six non-equivalent carbon atoms (Ca, Cb, Cc, Cc, Ce and Cf) present in compound B. The number of signals in each compound is equal to the number of carbon atoms present in a different chemical environment. Therefore, the compound B gives six signals in 13C NMR spectrum.

Conclusion

The given compound A gives five signals and compound B gives six signals in 13C NMR spectrum.

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Chapter 12C Solutions

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