Organic Chemistry: Principles and Mechanisms (Second Edition)
Organic Chemistry: Principles and Mechanisms (Second Edition)
2nd Edition
ISBN: 9780393663556
Author: Joel Karty
Publisher: W. W. Norton & Company
Question
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Chapter 16, Problem 16.39P
Interpretation Introduction

(a)

Interpretation:

The number of signals that would be generated in the 1H NMR spectrum for the given molecule is to be determined.

Concept introduction:

In 1H NMR, the number of signals is equal to the number of types of protons in the molecule. The chemically equivalent protons absorb at the same magnetic field and produce one signal whereas the chemically non-equivalent or distinct protons absorb at different magnetic fields, producing different signals.

Expert Solution
Check Mark

Answer to Problem 16.39P

The given molecule could generate two signals in 1H NMR spectrum because it has two distinct protons, as shown below:

Organic Chemistry: Principles and Mechanisms (Second Edition), Chapter 16, Problem 16.39P , additional homework tip  1

Explanation of Solution

The structure of the given compound is

Organic Chemistry: Principles and Mechanisms (Second Edition), Chapter 16, Problem 16.39P , additional homework tip  2

The given compound has a plane of symmetry and thus has two chemically distinct protons indicated as Ha and Hb, so there must be two signals in 1H NMR spectrum.

Organic Chemistry: Principles and Mechanisms (Second Edition), Chapter 16, Problem 16.39P , additional homework tip  3

Conclusion

It is determined that the given molecule has two signals in 1H NMR spectrum by determining the number of distinct protons in it.

Interpretation Introduction

(b)

Interpretation:

The number of signals that would be generated in the 1H NMR spectrum for the given molecule is to be determined.

Concept introduction:

In 1H NMR, the number of signals is equal to the number of types of protons in the molecule. The chemically equivalent protons absorb at the same magnetic field and produce one signal whereas the chemically non-equivalent or distinct protons absorb at different magnetic fields, producing different signals.

Expert Solution
Check Mark

Answer to Problem 16.39P

The given molecule could generate five signals in 1H NMR spectrum because it has five distinct protons, as shown below:

Organic Chemistry: Principles and Mechanisms (Second Edition), Chapter 16, Problem 16.39P , additional homework tip  4

Explanation of Solution

The structure of the given compound is

Organic Chemistry: Principles and Mechanisms (Second Edition), Chapter 16, Problem 16.39P , additional homework tip  5

The protons cis to chlorine atoms and those trans to chlorine atoms are diastereotropic. Thus, the compound has five chemically distinct protons indicated as Ha, Hb, Hc, Hd, and He, so there must be five signals in 1H NMR spectrum.

Organic Chemistry: Principles and Mechanisms (Second Edition), Chapter 16, Problem 16.39P , additional homework tip  6

Conclusion

It is determined that the given molecule has five signals in 1H NMR spectrum by determining the number of distinct protons in it.

Interpretation Introduction

(c)

Interpretation:

The number of signals that would be generated in the 1H NMR spectrum for the given molecule is to be determined.

Concept introduction:

In 1H NMR, the number of signals is equal to the number of types of protons in the molecule. The chemically equivalent protons absorb at the same magnetic field and produce one signal whereas the chemically non-equivalent or distinct protons absorb at different magnetic fields, producing different signals.

Expert Solution
Check Mark

Answer to Problem 16.39P

The given molecule could generate eight signals in 1H NMR spectrum because it has eight distinct protons, as shown below:

Organic Chemistry: Principles and Mechanisms (Second Edition), Chapter 16, Problem 16.39P , additional homework tip  7

Explanation of Solution

The structure of the given compound is

Organic Chemistry: Principles and Mechanisms (Second Edition), Chapter 16, Problem 16.39P , additional homework tip  8

As the ring has two different substituents, all the protons are chemically non-equivalent. Thus, the compound has eight chemically distinct protons indicated as Ha, Hb, Hc, Hd, He, Hf, and Hh, so there must be eight signals in 1H NMR spectrum.

Organic Chemistry: Principles and Mechanisms (Second Edition), Chapter 16, Problem 16.39P , additional homework tip  9

Conclusion

It is determined that the given molecule has eight signals in 1H NMR spectrum by determining the number of distinct protons in it.

Interpretation Introduction

(d)

Interpretation:

The number of signals that would be generated in the 1H NMR spectrum for the given molecule is to be determined.

Concept introduction:

In 1H NMR, the number of signals is equal to the number of types of protons in the molecule. The chemically equivalent protons absorb at the same magnetic field and produce one signal whereas the chemically non-equivalent or distinct protons absorb at different magnetic fields, producing different signals.

Expert Solution
Check Mark

Answer to Problem 16.39P

The given molecule could generate four signals in 1H NMR spectrum because it has four distinct protons, as shown below:

Organic Chemistry: Principles and Mechanisms (Second Edition), Chapter 16, Problem 16.39P , additional homework tip  10

Explanation of Solution

The structure of the given compound is

Organic Chemistry: Principles and Mechanisms (Second Edition), Chapter 16, Problem 16.39P , additional homework tip  11

In the given compounds, both ethyl groups are in different chemical environment. One is attached to oxygen and another to carbonyl carbon. Thus the compound has four chemically distinct protons indicated as Ha, Hb, Hc, and Hd, so there must be four signals in 1H NMR spectrum.

Organic Chemistry: Principles and Mechanisms (Second Edition), Chapter 16, Problem 16.39P , additional homework tip  12

Conclusion

It is determined that the given molecule has four signals in 1H NMR spectrum by determining the number of distinct protons in it.

Interpretation Introduction

(e)

Interpretation:

The number of signals that would be generated in the 1H NMR spectrum for the given molecule is to be determined.

Concept introduction:

In 1H NMR, the number of signals is equal to the number of types of protons in the molecule. The chemically equivalent protons absorb at the same magnetic field and produce one signal whereas the chemically non-equivalent or distinct protons absorb at different magnetic fields, producing different signals.

Expert Solution
Check Mark

Answer to Problem 16.39P

The given molecule could generate two signals in 1H NMR spectrum because it has two distinct protons, as shown below:

Organic Chemistry: Principles and Mechanisms (Second Edition), Chapter 16, Problem 16.39P , additional homework tip  13

Explanation of Solution

The structure of the given compound is

Organic Chemistry: Principles and Mechanisms (Second Edition), Chapter 16, Problem 16.39P , additional homework tip  14

In the given compounds, both ethyl groups are in the same chemical environment. Thus, the compound has two chemically distinct protons indicated as Ha and Hb, so there must be two signals in 1H NMR spectrum.

Organic Chemistry: Principles and Mechanisms (Second Edition), Chapter 16, Problem 16.39P , additional homework tip  15

Conclusion

It is determined that the given molecule has two signals in 1H NMR spectrum by determining the number of distinct protons in it.

Interpretation Introduction

(f)

Interpretation:

The number of signals that would be generated in the 1H NMR spectrum for the given molecule is to be determined.

Concept introduction:

In 1H NMR, the number of signals is equal to the number of types of protons in the molecule. The chemically equivalent protons absorb at the same magnetic field and produce one signal whereas the chemically non-equivalent or distinct protons absorb at different magnetic fields, producing different signals.

Expert Solution
Check Mark

Answer to Problem 16.39P

The given molecule could generate three signals in 1H NMR spectrum because it has three distinct protons, as shown below:

Organic Chemistry: Principles and Mechanisms (Second Edition), Chapter 16, Problem 16.39P , additional homework tip  16

Explanation of Solution

The structure of the given compound is

Organic Chemistry: Principles and Mechanisms (Second Edition), Chapter 16, Problem 16.39P , additional homework tip  17

As the molecule is para disubstituted, it has a plane of symmetry passing through Br-C-C-OH, which divides the aromatic protons in two types. Thus, the compound has three chemically distinct protons indicated as Ha,Hb, and Hc, so there must be three signals in 1H NMR spectrum.

Organic Chemistry: Principles and Mechanisms (Second Edition), Chapter 16, Problem 16.39P , additional homework tip  18

Conclusion

It is determined that the given molecule has three signals in 1H NMR spectrum by determining the number of distinct protons in it.

Interpretation Introduction

(g)

Interpretation:

The number of signals that would be generated in the 1H NMR spectrum for the given molecule is to be determined.

Concept introduction:

In 1H NMR, the number of signals is equal to the number of types of protons in the molecule. The chemically equivalent protons absorb at the same magnetic field and produce one signal whereas the chemically non-equivalent or distinct protons absorb at different magnetic fields, producing different signals.

Expert Solution
Check Mark

Answer to Problem 16.39P

The given molecule could generate five signals in 1H NMR spectrum because it has five distinct protons, as shown below:

Organic Chemistry: Principles and Mechanisms (Second Edition), Chapter 16, Problem 16.39P , additional homework tip  19

Explanation of Solution

The structure of the given compound is

Organic Chemistry: Principles and Mechanisms (Second Edition), Chapter 16, Problem 16.39P , additional homework tip  20

The molecule is meta disubstituted with different substituents and has no plane of symmetry; thus, all protons are chemically non-equivalent. Hence the compound has five chemically distinct protons indicated as Ha, Hc, Hd, He, and Hf, so there must be five signals in 1H NMR spectrum.

Organic Chemistry: Principles and Mechanisms (Second Edition), Chapter 16, Problem 16.39P , additional homework tip  21

Conclusion

It is determined that the given molecule has five signals in 1H NMR spectrum by determining the number of distinct protons in it.

Interpretation Introduction

(h)

Interpretation:

The number of signals that would be generated in the 1H NMR spectrum for the given molecule is to be determined.

Concept introduction:

In 1H NMR, the number of signals is equal to the number of types of protons in the molecule. The chemically equivalent protons absorb at the same magnetic field and produce one signal whereas the chemically non-equivalent or distinct protons absorb at different magnetic fields, producing different signals.

Expert Solution
Check Mark

Answer to Problem 16.39P

The given molecule could generate five signals in 1H NMR spectrum because it has five distinct protons, as shown below:

Organic Chemistry: Principles and Mechanisms (Second Edition), Chapter 16, Problem 16.39P , additional homework tip  22

Explanation of Solution

The structure of the given compound is

Organic Chemistry: Principles and Mechanisms (Second Edition), Chapter 16, Problem 16.39P , additional homework tip  23

The molecule is ortho disubstituted with different substituents and has no plane of symmetry; thus, all protons are chemically non-equivalent. Hence the compound has five chemically distinct protons indicated as Ha, Hc, Hd, He, and Hf, so there must be five signals in 1H NMR spectrum.

Organic Chemistry: Principles and Mechanisms (Second Edition), Chapter 16, Problem 16.39P , additional homework tip  24

Conclusion

It is determined that the given molecule has five signals in 1H NMR spectrum by determining the number of distinct protons in it.

Interpretation Introduction

(i)

Interpretation:

The number of signals that would be generated in the 1H NMR spectrum for the given molecule is to be determined.

Concept introduction:

In 1H NMR, the number of signals is equal to the number of types of protons in the molecule. The chemically equivalent protons absorb at the same magnetic field and produce one signal whereas the chemically non-equivalent or distinct protons absorb at different magnetic fields, producing different signals.

Expert Solution
Check Mark

Answer to Problem 16.39P

The given molecule could generate six signals in 1H NMR spectrum because it has six distinct protons, as shown below:

Organic Chemistry: Principles and Mechanisms (Second Edition), Chapter 16, Problem 16.39P , additional homework tip  25

Explanation of Solution

The structure of the given compound is

Organic Chemistry: Principles and Mechanisms (Second Edition), Chapter 16, Problem 16.39P , additional homework tip  26

The molecule is monosubstituted benzene; thus, there are three types of aromatic protons. The three methyl protons are in same chemical environment; thus they are identical. Hence the compound has six chemically distinct protons indicated as Ha, Hc, Hd, He, and Hf, so there must be six signals in 1H NMR spectrum.

Organic Chemistry: Principles and Mechanisms (Second Edition), Chapter 16, Problem 16.39P , additional homework tip  27

Conclusion

It is determined that the given molecule has six signals in 1H NMR spectrum by determining the number of distinct protons in it.

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Chapter 16 Solutions

Organic Chemistry: Principles and Mechanisms (Second Edition)

Ch. 16 - Prob. 16.11PCh. 16 - Prob. 16.12PCh. 16 - Prob. 16.13PCh. 16 - Prob. 16.14PCh. 16 - Prob. 16.15PCh. 16 - Prob. 16.16PCh. 16 - Prob. 16.17PCh. 16 - Prob. 16.18PCh. 16 - Prob. 16.19PCh. 16 - Prob. 16.20PCh. 16 - Prob. 16.21PCh. 16 - Prob. 16.22PCh. 16 - Prob. 16.23PCh. 16 - Prob. 16.24PCh. 16 - Prob. 16.25PCh. 16 - Prob. 16.26PCh. 16 - Prob. 16.27PCh. 16 - Prob. 16.28PCh. 16 - Prob. 16.29PCh. 16 - Prob. 16.30PCh. 16 - Prob. 16.31PCh. 16 - Prob. 16.32PCh. 16 - Prob. 16.33PCh. 16 - Prob. 16.34PCh. 16 - Prob. 16.35PCh. 16 - Prob. 16.36PCh. 16 - Prob. 16.37PCh. 16 - Prob. 16.38PCh. 16 - Prob. 16.39PCh. 16 - Prob. 16.40PCh. 16 - Prob. 16.41PCh. 16 - Prob. 16.42PCh. 16 - Prob. 16.43PCh. 16 - Prob. 16.44PCh. 16 - Prob. 16.45PCh. 16 - Prob. 16.46PCh. 16 - Prob. 16.47PCh. 16 - Prob. 16.48PCh. 16 - Prob. 16.49PCh. 16 - Prob. 16.50PCh. 16 - Prob. 16.51PCh. 16 - Prob. 16.52PCh. 16 - Prob. 16.53PCh. 16 - Prob. 16.54PCh. 16 - Prob. 16.55PCh. 16 - Prob. 16.56PCh. 16 - Prob. 16.57PCh. 16 - Prob. 16.58PCh. 16 - Prob. 16.59PCh. 16 - Prob. 16.60PCh. 16 - Prob. 16.61PCh. 16 - Prob. 16.62PCh. 16 - Prob. 16.63PCh. 16 - Prob. 16.64PCh. 16 - Prob. 16.65PCh. 16 - Prob. 16.66PCh. 16 - Prob. 16.67PCh. 16 - Prob. 16.68PCh. 16 - Prob. 16.69PCh. 16 - Prob. 16.70PCh. 16 - Prob. 16.71PCh. 16 - Prob. 16.72PCh. 16 - Prob. 16.73PCh. 16 - Prob. 16.74PCh. 16 - Prob. 16.75PCh. 16 - Prob. 16.76PCh. 16 - Prob. 16.77PCh. 16 - Prob. 16.78PCh. 16 - Prob. 16.79PCh. 16 - Prob. 16.80PCh. 16 - Prob. 16.81PCh. 16 - Prob. 16.82PCh. 16 - Prob. 16.83PCh. 16 - Prob. 16.84PCh. 16 - Prob. 16.85PCh. 16 - Prob. 16.86PCh. 16 - Prob. 16.87PCh. 16 - Prob. 16.88PCh. 16 - Prob. 16.89PCh. 16 - Prob. 16.1YTCh. 16 - Prob. 16.2YTCh. 16 - Prob. 16.3YTCh. 16 - Prob. 16.4YTCh. 16 - Prob. 16.5YTCh. 16 - Prob. 16.6YTCh. 16 - Prob. 16.7YTCh. 16 - Prob. 16.8YTCh. 16 - Prob. 16.9YTCh. 16 - Prob. 16.10YTCh. 16 - Prob. 16.11YTCh. 16 - Prob. 16.12YTCh. 16 - Prob. 16.13YTCh. 16 - Prob. 16.14YTCh. 16 - Prob. 16.15YTCh. 16 - Prob. 16.16YTCh. 16 - Prob. 16.17YTCh. 16 - Prob. 16.18YTCh. 16 - Prob. 16.19YTCh. 16 - Prob. 16.20YTCh. 16 - Prob. 16.21YTCh. 16 - Prob. 16.22YTCh. 16 - Prob. 16.23YTCh. 16 - Prob. 16.24YTCh. 16 - Prob. 16.25YTCh. 16 - Prob. 16.26YTCh. 16 - Prob. 16.27YTCh. 16 - Prob. 16.28YTCh. 16 - Prob. 16.29YTCh. 16 - Prob. 16.30YTCh. 16 - Prob. 16.31YTCh. 16 - Prob. 16.32YTCh. 16 - Prob. 16.33YTCh. 16 - Prob. 16.34YT
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