ORGANIC CHEMISTRY
ORGANIC CHEMISTRY
5th Edition
ISBN: 9781259977596
Author: SMITH
Publisher: MCG
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Chapter 14, Problem 14.3P

How many 1 H NMR signals does each compound show?

a. Chapter 14, Problem 14.3P, How many  NMR signals does each compound show?

a. 	c.  e.   g. 

b.  	d.   f. 	      h. 
 , example  1 c. Chapter 14, Problem 14.3P, How many  NMR signals does each compound show?

a. 	c.  e.   g. 

b.  	d.   f. 	      h. 
 , example  2 e. Chapter 14, Problem 14.3P, How many  NMR signals does each compound show?

a. 	c.  e.   g. 

b.  	d.   f. 	      h. 
 , example  3 g. Chapter 14, Problem 14.3P, How many  NMR signals does each compound show?

a. 	c.  e.   g. 

b.  	d.   f. 	      h. 
 , example  4

b. Chapter 14, Problem 14.3P, How many  NMR signals does each compound show?

a. 	c.  e.   g. 

b.  	d.   f. 	      h. 
 , example  5 d. Chapter 14, Problem 14.3P, How many  NMR signals does each compound show?

a. 	c.  e.   g. 

b.  	d.   f. 	      h. 
 , example  6 f. Chapter 14, Problem 14.3P, How many  NMR signals does each compound show?

a. 	c.  e.   g. 

b.  	d.   f. 	      h. 
 , example  7 h. Chapter 14, Problem 14.3P, How many  NMR signals does each compound show?

a. 	c.  e.   g. 

b.  	d.   f. 	      h. 
 , example  8

Expert Solution
Check Mark
Interpretation Introduction

(a)

Interpretation: The number of 1H NMR signals in the given compound 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. Protons which are present in the same chemical environment that is between the same group of atoms are known as chemically equivalent protons and in 1HNMR all chemically equivalent proton generates one signal or one peak, whereas non-equivalent proton generates different signals.

Answer to Problem 14.3P

The given compound, propane shows two signals in 1H NMR spectrum.

Explanation of Solution

The number of signals in each compound is equal to the number of hydrogen atoms present in a different chemical environment. The given compound is propane that consists of two non-equivalent hydrogen groups. Therefore, the number of 1H NMR signals shown by propane is two.

ORGANIC CHEMISTRY, Chapter 14, Problem 14.3P , additional homework tip  1

Figure 1

Conclusion

The given compound, propane shows two signals in 1H NMR spectrum.

Expert Solution
Check Mark
Interpretation Introduction

(b)

Interpretation: The number of 1H NMR signals in the given compound 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. Protons which are present in the same chemical environment that is between the same group of atoms are known as chemically equivalent protons and in 1HNMR all chemically equivalent proton generates one signal or one peak, whereas non-equivalent proton generates different signals.

Answer to Problem 14.3P

The given compound, ethoxyethane shows two signals in 1H NMR spectrum.

Explanation of Solution

The given compound is ethoxyethane that consists of two non-equivalent hydrogen groups. Therefore, the number of 1H NMR signals shown by ethoxyethane is two.

ORGANIC CHEMISTRY, Chapter 14, Problem 14.3P , additional homework tip  2

Figure 2

Conclusion

The given compound, ethoxyethane shows two signals in 1H NMR spectrum.

Expert Solution
Check Mark
Interpretation Introduction

(c)

Interpretation: The number of 1H NMR signals in the given compound 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. Protons which are present in the same chemical environment that is between the same group of atoms are known as chemically equivalent protons and in 1HNMR all chemically equivalent proton generates one signal or one peak, whereas non-equivalent proton generates different signals.

Answer to Problem 14.3P

The given compound, butane shows two signals in 1H NMR spectrum.

Explanation of Solution

The given compound is butane that consists of two non-equivalent hydrogen groups. Therefore, the number of 1H NMR signals shown by butane is two as shown below.

ORGANIC CHEMISTRY, Chapter 14, Problem 14.3P , additional homework tip  3

Figure 3

Conclusion

The given compound, butane shows two signals in 1H NMR spectrum.

Expert Solution
Check Mark
Interpretation Introduction

(d)

Interpretation: The number of 1H NMR signals in the given compound 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. Protons which are present in the same chemical environment that is between the same group of atoms are known as chemically equivalent protons and in 1HNMR all chemically equivalent proton generates one signal or one peak, whereas non-equivalent proton generates different signals.

Answer to Problem 14.3P

The given compound, 2,3 dimethylbutane shows two signals in 1H NMR spectrum.

Explanation of Solution

The given compound is 2,3 dimethylbutane that consists of two non-equivalent hydrogen groups. Therefore, the number of 1H NMR signals shown by 2,3 dimethylbutane is two as shown below.

ORGANIC CHEMISTRY, Chapter 14, Problem 14.3P , additional homework tip  4

Figure 4

Conclusion

The given compound, 2,3 dimethylbutane shows two signals in 1H NMR spectrum.

Expert Solution
Check Mark
Interpretation Introduction

(e)

Interpretation: The number of 1H NMR signals in the given compound 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. Protons which are present in the same chemical environment that is between the same group of atoms are known as chemically equivalent protons and in 1HNMR all chemically equivalent proton generates one signal or one peak, whereas non-equivalent proton generates different signals.

Answer to Problem 14.3P

The given compound, ethyl propanoate shows four signals in 1H NMR spectrum.

Explanation of Solution

The given compound is ethyl propanoate that consists of four non-equivalent hydrogen groups. Therefore, the number of 1H NMR signals shown by ethyl propanoate is four as shown below.

ORGANIC CHEMISTRY, Chapter 14, Problem 14.3P , additional homework tip  5

Figure 5

Conclusion

The given compound, ethyl propanoate shows four signals in 1H NMR spectrum.

Expert Solution
Check Mark
Interpretation Introduction

(f)

Interpretation: The number of 1H NMR signals in the given compound 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. Protons which are present in the same chemical environment that is between the same group of atoms are known as chemically equivalent protons and in 1HNMR all chemically equivalent proton generates one signal or one peak, whereas non-equivalent proton generates different signals.

Answer to Problem 14.3P

The given compound, 1methoxy2methyl propane shows four signals in 1H NMR spectrum.

Explanation of Solution

The given compound is 1methoxy2methyl propane that consists of four non-equivalent hydrogen groups. Therefore, the number of 1H NMR signals shown by 1methoxy2methyl propane is four as shown below.

ORGANIC CHEMISTRY, Chapter 14, Problem 14.3P , additional homework tip  6

Figure 6

Conclusion

The given compound, 1methoxy2methyl propane shows four signals in 1H NMR spectrum.

Expert Solution
Check Mark
Interpretation Introduction

(g)

Interpretation: The number of 1H NMR signals in the given compound 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. Protons which are present in the same chemical environment that is between the same group of atoms are known as chemically equivalent protons and in 1HNMR all chemically equivalent proton generates one signal or one peak, whereas non-equivalent proton generates different signals.

Answer to Problem 14.3P

The given compound, 1 chlorooctane shows eight signals in 1H NMR spectrum.

Explanation of Solution

The given compound is 1 chlorooctane that consists of eight non-equivalent hydrogen groups. Therefore, the number of 1H NMR signals shown by 1 chlorooctane is eight as shown below.

ORGANIC CHEMISTRY, Chapter 14, Problem 14.3P , additional homework tip  7

Figure 7

Conclusion

The given compound, 1 chlorooctane shows eight signals in 1H NMR spectrum.

Expert Solution
Check Mark
Interpretation Introduction

(h)

Interpretation: The number of 1H NMR signals in the given compound 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. Protons which are present in the same chemical environment that is between the same group of atoms are known as chemically equivalent protons and in 1HNMR all chemically equivalent proton generates one signal or one peak, whereas non-equivalent proton generates different signals.

Answer to Problem 14.3P

The given compound, propan1ol shows four signals in 1H NMR spectrum.

Explanation of Solution

The given compound is propan1ol that consists of four non-equivalent hydrogen groups. Therefore, the number of 1H NMR signals shown by propan1ol is four as shown below.

ORGANIC CHEMISTRY, Chapter 14, Problem 14.3P , additional homework tip  8

Figure 8

Conclusion

The given compound, propan1ol shows four signals in 1H NMR spectrum.

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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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