ORGANIC CHEMISTRY
ORGANIC CHEMISTRY
5th Edition
ISBN: 9781259977596
Author: SMITH
Publisher: MCG
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Chapter 14, Problem 14.36P
Interpretation Introduction

(a)

Interpretation: The different types of protons present in given compound are 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
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Answer to Problem 14.36P

In the given compound, two different types of protons are present.

Explanation of Solution

In the given compound, one carbon atom is bonded to three other carbon atoms on which three hydrogen atoms are present. The central carbon atom will give multiplet whereas the other three carbon atoms will give doublet in NMR spectroscopy. The splitting of peaks takes place according to n+1 rule. Hence, the given compound contains two different protons.

ORGANIC CHEMISTRY, Chapter 14, Problem 14.36P , additional homework tip  1

Conclusion

In the given compound, two different types of protons are present.

Interpretation Introduction

(b)

Interpretation: The different types of protons present in given compound are 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 14.36P

In the given compound, seven different types of protons are present.

Explanation of Solution

The given compound contains seven different types of protons each labeled as Ha, Hb, Hc, Hd, He, Hf and Hg as shown in Figure 1.

ORGANIC CHEMISTRY, Chapter 14, Problem 14.36P , additional homework tip  2

Figure 1

Each proton will give different chemical shift value in NMR spectroscopy.

Conclusion

In the given compound, seven different types of protons are present.

Interpretation Introduction

(c)

Interpretation: The different types of protons present in given compound are 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
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Answer to Problem 14.36P

In the given compound, five different types of protons are present.

Explanation of Solution

The given compound contains five different types of protons each labeled as Ha, Hb, Hc, Hd and He as shown in Figure 2.

ORGANIC CHEMISTRY, Chapter 14, Problem 14.36P , additional homework tip  3

Figure 2

Each proton will give different chemical shift value in NMR spectroscopy.

Conclusion

In the given compound, five different types of protons are present.

Interpretation Introduction

(d)

Interpretation: The different types of protons present in given compound are 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 14.36P

In the given compound, three different types of protons are present.

Explanation of Solution

The given compound contains three different types of protons each labeled as Ha, Hb and Hc as shown in Figure 3.

ORGANIC CHEMISTRY, Chapter 14, Problem 14.36P , additional homework tip  4

Figure 3

Each proton will give different chemical shift value in NMR spectroscopy.

Conclusion

In the given compound, three different types of protons are present.

Interpretation Introduction

(e)

Interpretation: The different types of protons present in given compound are 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 14.36P

In the given compound three different types of protons are present.

Explanation of Solution

The given compound contains three different types of protons each labeled as Ha, Hb and Hc as shown in Figure 4.

ORGANIC CHEMISTRY, Chapter 14, Problem 14.36P , additional homework tip  5

Figure 4

Each proton will give different chemical shift value in NMR spectroscopy.

Conclusion

In the given compound, three different types of protons are present.

Interpretation Introduction

(f)

Interpretation: The different types of protons present in given compound are 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
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Answer to Problem 14.36P

In the given compound four different types of protons are present.

Explanation of Solution

The given compound contains four different types of protons each labeled as Ha, Hb, Hc and Hd as shown in Figure 5.

ORGANIC CHEMISTRY, Chapter 14, Problem 14.36P , additional homework tip  6

Figure 5

Each proton will give different chemical shift value in NMR spectroscopy.

Conclusion

In the given compound four different types of protons are present.

Interpretation Introduction

(g)

Interpretation: The different types of protons present in given compound are 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
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Answer to Problem 14.36P

In the given compound, six different types of protons are present.

Explanation of Solution

In the given compound, a chiral carbon atom is bonded to another carbon atom on which two protons and an methyl group is present. Hence, these protons are termed as diasterotropic protons. Each diasterotropic protons gives different chemical shift value.

Therefore, the given compound contains six different types of protons each labeled as Ha, Hb, Hc, Hd, He and Hf as shown in Figure 6.

ORGANIC CHEMISTRY, Chapter 14, Problem 14.36P , additional homework tip  7

Figure 6

Each proton will give different chemical shift value in NMR spectroscopy.

Conclusion

In the given compound, six different types of protons are present.

Interpretation Introduction

(h)

Interpretation: The different types of protons present in given compound are 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 14.36P

In the given compound four different types of protons are present.

Explanation of Solution

The given compound contains four different types of protons each labeled as Ha, Hb, Hc and Hd as shown in Figure 7.

ORGANIC CHEMISTRY, Chapter 14, Problem 14.36P , additional homework tip  8

Figure 7

Each proton will give different chemical shift value in NMR spectroscopy.

Conclusion

In the given compound four different types of protons are present.

Interpretation Introduction

(i)

Interpretation: The different types of protons present in given compound are 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 14.36P

In the given compound, three different types of protons are present.

Explanation of Solution

The given compound contains three different types of protons each labeled as Ha, Hb and Hc as shown in Figure 8.

ORGANIC CHEMISTRY, Chapter 14, Problem 14.36P , additional homework tip  9

Figure 8

Each proton will give different chemical shift value in NMR spectroscopy.

Conclusion

In the given compound, three different types of protons are present.

Interpretation Introduction

(j)

Interpretation: The different types of protons present in given compound are 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 14.36P

In the given compound four different types of protons are present.

Explanation of Solution

In the given compound, diastereotropic protons are present on two carbon atoms. However, due to symmetry of the molecule, one peak is observed.

Therefore, the given compound contains four different types of protons each labeled as Ha, Hb, Hc and Hd as shown in Figure 9.

ORGANIC CHEMISTRY, Chapter 14, Problem 14.36P , additional homework tip  10

Figure 9

Each proton will give different chemical shift value in NMR spectroscopy.

Conclusion

In the given compound four different types of protons are present.

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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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