Organic Chemistry
Organic Chemistry
5th Edition
ISBN: 9780078021558
Author: Janice Gorzynski Smith Dr.
Publisher: McGraw-Hill Education
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Chapter 14, Problem 14.42P
Interpretation Introduction

(a)

Interpretation: The number of peaks into which each single of labeled proton will split is to be predicted.

Concept introduction: Spectroscopy method is used to identify the structure of the molecule. It is based on the interactions between matter and electromagnetic radiations. Proton NMR spectroscopy identifies the number of hydrogen atoms present in a molecule and the nature of the functional group. The value of chemical peaks depends upon the chemical environment around the hydrogen atom.

Expert Solution
Check Mark

Answer to Problem 14.42P

The signal of proton Ha and proton Hb will split into doublet and quartet, respectively.

Explanation of Solution

In NMR spectroscopy, splitting of signal takes place according to number of protons present on neighboring carbon atom. The number of peaks into which a signal will split is n+1. Here, n is the number of protons present on neighboring carbon atom.

In the given compound, carbon atom of labeled proton Ha is bonded to another carbon atom on which one hydrogen atom is present whereas carbon atom of labeled proton Hb is bonded to another carbon atom on which three hydrogen atoms are present. Hence, the signal of proton Ha and proton Hb will split into doublet and quartet, respectively.

Conclusion

The signal of proton Ha and proton Hb will split into doublet and quartet, respectively.

Interpretation Introduction

(b)

Interpretation: The number of peaks into which each single of labeled proton will split is to be predicted.

Concept introduction: Spectroscopy method is used to identify the structure of the molecule. It is based on the interactions between matter and electromagnetic radiations. Proton NMR spectroscopy identifies the number of hydrogen atoms present in a molecule and the nature of the functional group. The value of chemical peaks depends upon the chemical environment around the hydrogen atom.

Expert Solution
Check Mark

Answer to Problem 14.42P

The signal of proton Ha and proton Hb will split into triplet.

Explanation of Solution

In NMR spectroscopy, splitting of signal takes place according to number of protons present on neighboring carbon atom. The number of peaks into which a signal will split is n+1. Here, n is the number of protons present on neighboring carbon atom.

In the given compound, carbon atom of labeled proton Ha and proton Hb is bonded to another carbon atom on which two hydrogen atoms are present. Hence, the signal of proton Ha and proton Hb will split into triplet.

Conclusion

The signal of proton Ha and proton Hb will split into triplet.

Interpretation Introduction

(c)

Interpretation: The number of peaks into which each single of labeled proton will split is to be predicted.

Concept introduction: Spectroscopy method is used to identify the structure of the molecule. It is based on the interactions between matter and electromagnetic radiations. Proton NMR spectroscopy identifies the number of hydrogen atoms present in a molecule and the nature of the functional group. The value of chemical peaks depends upon the chemical environment around the hydrogen atom.

Expert Solution
Check Mark

Answer to Problem 14.42P

The signal of proton Ha and proton Hb will split into doublet and triplet, respectively.

Explanation of Solution

In NMR spectroscopy, splitting of signal takes place according to number of protons present on neighboring carbon atom. The number of peaks into which a signal will split is n+1. Here, n is the number of protons present on neighboring carbon atom.

In the given compound, carbon atom of labeled proton Ha is bonded to another carbon atom on which one hydrogen atom is present whereas carbon atom of labeled proton Hb is bonded to another carbon atom on which two hydrogen atoms are present. Hence, the signal of proton Ha and proton Hb will split into doublet and triplet, respectively.

Conclusion

The signal of proton Ha and proton Hb will split into doublet and triplet, respectively.

Interpretation Introduction

(d)

Interpretation: The number of peaks into which each single of labeled proton will split is to be predicted.

Concept introduction: Spectroscopy method is used to identify the structure of the molecule. It is based on the interactions between matter and electromagnetic radiations. Proton NMR spectroscopy identifies the number of hydrogen atoms present in a molecule and the nature of the functional group. The value of chemical peaks depends upon the chemical environment around the hydrogen atom.

Expert Solution
Check Mark

Answer to Problem 14.42P

The signal of proton Ha, Hb, Hc and Hd will split into doublet, septet, quartet and triplet, respectively.

Explanation of Solution

In NMR spectroscopy, splitting of signal takes place according to number of protons present on neighboring carbon atom. The number of peaks into which a signal will split is n+1. Here, n is the number of protons present on neighboring carbon atom.

In the given compound, carbon atom of labeled proton Ha, Hb, Hc and Hd is bonded to another carbon atom on which one, six, three and two hydrogen atom is present Hence, the signal of proton Ha, Hb, Hc and Hd will split into doublet, septet, quartet and triplet, respectively.

Conclusion

The signal of proton Ha, Hb, Hc and Hd will split into doublet, septet, quartet and triplet, respectively.

Interpretation Introduction

(e)

Interpretation: The number of peaks into which each single of labeled proton will split is to be predicted.

Concept introduction: Spectroscopy method is used to identify the structure of the molecule. It is based on the interactions between matter and electromagnetic radiations. Proton NMR spectroscopy identifies the number of hydrogen atoms present in a molecule and the nature of the functional group. The value of chemical peaks depends upon the chemical environment around the hydrogen atom.

Expert Solution
Check Mark

Answer to Problem 14.42P

The signal of proton Ha, Hb, Hc and Hd will split into doublet, septet, quartet and triplet, respectively.

Explanation of Solution

In NMR spectroscopy, splitting of signal takes place according to number of protons present on neighboring carbon atom. The number of peaks into which a signal will split is n+1. Here, n is the number of protons present on neighboring carbon atom.

In the given compound, carbon atom of labeled proton Ha is bonded to two carbon atoms on which two hydrogen atoms are present whereas carbon atom of labeled proton Hb is bonded to another carbon atom on which two hydrogen atoms are present. Hence, the signal of proton Ha and proton Hb will split into pentet and triplet, respectively.

Conclusion

The signal of proton Ha, Hb, Hc and Hd will split into doublet, septet, quartet and triplet, respectively.

Interpretation Introduction

(f)

Interpretation: The number of peaks into which each single of labeled proton will split is to be predicted.

Concept introduction: Spectroscopy method is used to identify the structure of the molecule. It is based on the interactions between matter and electromagnetic radiations. Proton NMR spectroscopy identifies the number of hydrogen atoms present in a molecule and the nature of the functional group. The value of chemical peaks depends upon the chemical environment around the hydrogen atom.

Expert Solution
Check Mark

Answer to Problem 14.42P

The signal of proton Ha, Hb, Hc and Hd will split into triplet, sextet, pentet and triplet, respectively.

Explanation of Solution

In NMR spectroscopy, splitting of signal takes place according to number of protons present on neighboring carbon atom. The number of peaks into which a signal will split is n+1. Here, n is the number of protons present on neighboring carbon atom.

The splitting pattern shown by each labeled proton is show in Figure 1.

Organic Chemistry, Chapter 14, Problem 14.42P , additional homework tip  1

Figure 1

Conclusion

The signal of proton Ha, Hb, Hc and Hd will split into triplet, sextet, pentet and triplet, respectively.

Interpretation Introduction

(g)

Interpretation: The number of peaks into which each single of labeled proton will split is to be predicted.

Concept introduction: Spectroscopy method is used to identify the structure of the molecule. It is based on the interactions between matter and electromagnetic radiations. Proton NMR spectroscopy identifies the number of hydrogen atoms present in a molecule and the nature of the functional group. The value of chemical peaks depends upon the chemical environment around the hydrogen atom.

Expert Solution
Check Mark

Answer to Problem 14.42P

The signal of proton Ha, Hb, Hc and Hd will split into triplet, sextet, pentet and triplet, respectively.

Explanation of Solution

In NMR spectroscopy, splitting of signal takes place according to number of protons present on neighboring carbon atom. The number of peaks into which a signal will split is n+1. Here, n is the number of protons present on neighboring carbon atom.

The splitting pattern shown by each labeled proton is show in Figure 2.

Organic Chemistry, Chapter 14, Problem 14.42P , additional homework tip  2

Figure 2

Conclusion

The signal of proton Ha, Hb, Hc and Hd will split into triplet, sextet, pentet and triplet, respectively.

Interpretation Introduction

(h)

Interpretation: The number of peaks into which each single of labeled proton will split is to be predicted.

Concept introduction: Spectroscopy method is used to identify the structure of the molecule. It is based on the interactions between matter and electromagnetic radiations. Proton NMR spectroscopy identifies the number of hydrogen atoms present in a molecule and the nature of the functional group. The value of chemical peaks depends upon the chemical environment around the hydrogen atom.

Expert Solution
Check Mark

Answer to Problem 14.42P

The signal of proton Ha and Hb will split into pentet and triplet, respectively.

Explanation of Solution

In NMR spectroscopy, splitting of signal takes place according to number of protons present on neighboring carbon atom. The number of peaks into which a signal will split is n+1. Here, n is the number of protons present on neighboring carbon atom.

The splitting pattern shown by each labeled proton is show in Figure 3.

Organic Chemistry, Chapter 14, Problem 14.42P , additional homework tip  3

Figure 3

Conclusion

The signal of proton Ha and Hb will split into pentet and triplet, respectively.

Interpretation Introduction

(i)

Interpretation: The number of peaks into which each single of labeled proton will split is to be predicted.

Concept introduction: Spectroscopy method is used to identify the structure of the molecule. It is based on the interactions between matter and electromagnetic radiations. Proton NMR spectroscopy identifies the number of hydrogen atoms present in a molecule and the nature of the functional group. The value of chemical peaks depends upon the chemical environment around the hydrogen atom.

Expert Solution
Check Mark

Answer to Problem 14.42P

The signal of proton Ha and Hb will split into doublet.

Explanation of Solution

In NMR spectroscopy, splitting of signal takes place according to number of protons present on neighboring carbon atom. The number of peaks into which a signal will split is n+1. Here, n is the number of protons present on neighboring carbon atom.

The splitting pattern shown by each labeled proton is show in Figure 4.

Organic Chemistry, Chapter 14, Problem 14.42P , additional homework tip  4

Figure 4

Conclusion

The signal of proton Ha and Hb will split into doublet.

Interpretation Introduction

(j)

Interpretation: The number of peaks into which each single of labeled proton will split is to be predicted.

Concept introduction: Spectroscopy method is used to identify the structure of the molecule. It is based on the interactions between matter and electromagnetic radiations. Proton NMR spectroscopy identifies the number of hydrogen atoms present in a molecule and the nature of the functional group. The value of chemical peaks depends upon the chemical environment around the hydrogen atom.

Expert Solution
Check Mark

Answer to Problem 14.42P

The signal of proton Ha, Hb and Hc will split into multiplet, doublet and doublet, respectively.

Explanation of Solution

In NMR spectroscopy, splitting of signal takes place according to number of protons present on neighboring carbon atom. The number of peaks into which a signal will split is n+1. Here, n is the number of protons present on neighboring carbon atom.

The splitting pattern shown by each labeled proton is show in Figure 5.

Organic Chemistry, Chapter 14, Problem 14.42P , additional homework tip  5

Figure 5

Conclusion

The signal of proton Ha, Hb and Hc will split into multiplet, doublet and doublet, respectively.

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Chapter 14 Solutions

Organic Chemistry

Ch. 14 - Prob. 14.11PCh. 14 - Problem 14.12 Which compound give a NMR spectrum...Ch. 14 - Prob. 14.13PCh. 14 - Prob. 14.14PCh. 14 - For each compound give the number of 1H NMR...Ch. 14 - Prob. 14.16PCh. 14 - Prob. 14.17PCh. 14 - Problem 14.18 Describe the NMR spectrum of each...Ch. 14 - Problem 14.19 Draw a splitting diagram for in ,...Ch. 14 - Problem 14.20 Identify A and B, isomers of...Ch. 14 - Problem 14.21 How many signals are present in the ...Ch. 14 - Problem 14.22 What protons in alcohol A give rise...Ch. 14 - How many peaks are observed in the NMR signal for...Ch. 14 - Problem 14.24 Propose a structure for a compound...Ch. 14 - Problem 14.25 Propose a structure for a compound...Ch. 14 - Problem 14.26. Identify products A and B from the...Ch. 14 - Problem 14.27 How many lines are observed in the ...Ch. 14 - Problem 14.28 Draw all constitutional isomers of...Ch. 14 - Problem 14.29 Esters of chrysanthemic acid are...Ch. 14 - Prob. 14.30PCh. 14 - Problem 14.31 Identify the carbon atoms that give...Ch. 14 - Problem 14.32 A compound of molecular formula ...Ch. 14 - Problem 14.33 Draw the structure of a compound of...Ch. 14 - 14.34 (a) How many NMR signals does each of the...Ch. 14 - 14.35 (a) How many NMR signals does each compound...Ch. 14 - Prob. 14.36PCh. 14 - 14.37 How many NMR signals does each natural...Ch. 14 - Prob. 14.38PCh. 14 - 14.39 What effect does increasing the operating...Ch. 14 - Prob. 14.40PCh. 14 - 14.41 How could you use chemical shift and...Ch. 14 - Prob. 14.42PCh. 14 - 14.43 How can you use NMR spectroscopy to...Ch. 14 - Prob. 14.44PCh. 14 - Prob. 14.45PCh. 14 - Prob. 14.46PCh. 14 - Prob. 14.47PCh. 14 - 14.48 How many NMR signals does each compound...Ch. 14 - 14.49 Rank the highlighted carbon atoms in each...Ch. 14 - 14.50 Identify the carbon atoms that give rise to...Ch. 14 - 14.51 a. How many signals does dimethyl...Ch. 14 - 14.52 Answer the following questions about each of...Ch. 14 - 14.53 Propose a structure consistent with each set...Ch. 14 - 14.54 Identify the structures of isomers A and B...Ch. 14 - 14.55 Reaction of with affords compound W,...Ch. 14 - 14.56 Treatment of with , followed by aqueous ...Ch. 14 - 14.57 Compound C has a molecular ion in its mass...Ch. 14 - 14.58 As we will learn in Chapter 20, reaction of ...Ch. 14 - 14.59 Identify the structures of isomers E and F...Ch. 14 - 14.59 Identify the structures of isomers H and I...Ch. 14 - 14.61 Propose a structure consistent with each set...Ch. 14 - 14.62 Reaction of with , followed by treatment...Ch. 14 - Reaction of aldehyde D with amino alcohol E in the...Ch. 14 - 14.64 Propose a structure consistent with each set...Ch. 14 - 14.65 In the presence of a small amount of acid, a...Ch. 14 - 14.66 Treatment of with affords two products (M...Ch. 14 - 14.67 Compound O has molecular formula and shows...Ch. 14 - 14.68 Compound P has molecular formula . Deduce...Ch. 14 - 14.69 Treatment of with strong base followed by ...Ch. 14 - 14.70 When -bromo--dimethylbutane is treated with...Ch. 14 - 14.71 Propose a structure consistent with each set...Ch. 14 - 14.72 Reaction of unknown A with forms...Ch. 14 - Prob. 14.73PCh. 14 - 14.74 -Annulene shows two signals in its ...Ch. 14 - 14.75 Explain why the spectrum of-methylbutan--ol...Ch. 14 - 14.76 Because has an odd mass number, nuclei...Ch. 14 - 14.77 Cyclohex--enone has two protons on its...
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