Organic Chemistry-Package(Custom)
Organic Chemistry-Package(Custom)
4th Edition
ISBN: 9781259141089
Author: SMITH
Publisher: MCG
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Chapter 14, Problem 14.17P

Describe the 1 H NMR spectrum of each compound. State how many NMR signals are present,

the splitting pattern for each signal, and the approximate chemical shift?

Chapter 14, Problem 14.17P, Describe the 1H NMR spectrum of each compound. State how many NMR signals are present,  the

Expert Solution
Check Mark
Interpretation Introduction

(a)

Interpretation:

The 1H NMR spectrum of the given compound is to be described. The number of NMR signals, the splitting pattern for each signal and the approximate chemical shift values are to be stated.

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. On the horizontal axis, the position of absorption is generally referred to as chemical shift.

Answer to Problem 14.17P

The 1H NMR spectrum of the given compound is,

Organic Chemistry-Package(Custom), Chapter 14, Problem 14.17P , additional homework tip  1

The number of NMR signals, the splitting pattern for each signal and the approximate chemical shift values are rightfully stated.

Explanation of Solution

The given compound is ethyl methyl ether (CH3OCH2CH3). It contains three types of proton Ha, Hb and Hc. Therefore, it gives three signals in 1H NMR spectrum. The 1H NMR spectrum of the given compound is shown below.

Organic Chemistry-Package(Custom), Chapter 14, Problem 14.17P , additional homework tip  2

Figure 1

The proton Ha gets split into a singlet because it has no adjacent proton, the proton Hb gets split into a quartet by 3Hc protons and the proton Hc gets split into a triplet by 2Hb protons. The chemical shift of Ha is approximately 3.3 ppm. The chemical shift of Hb is approximately 3.5 ppm and the chemical shift of Hc is approximately 1.1 ppm.

Conclusion

The 1H NMR spectrum of the given compound is shown in Figure 1. It gives three signals with one, four and three peaks.

Expert Solution
Check Mark
Interpretation Introduction

(b)

Interpretation:

The 1H NMR spectrum of the given compound is to be described. The number of NMR signals, the splitting pattern for each signal and the approximate chemical shift values are to be stated.

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. On the horizontal axis, the position of absorption is generally referred to as chemical shift.

Answer to Problem 14.17P

The 1H NMR spectrum of the given compound is,

Organic Chemistry-Package(Custom), Chapter 14, Problem 14.17P , additional homework tip  3

The number of NMR signals, the splitting pattern for each signal and the approximate chemical shift values are rightfully stated.

Explanation of Solution

The given compound is isopropylpropionate (CH3CH2COOCH(CH3)2). It contains four types of proton Ha, Hb, Hc and Hd. Therefore, it gives four signals in 1H NMR spectrum. The 1H NMR spectrum of the given compound is shown below.

Organic Chemistry-Package(Custom), Chapter 14, Problem 14.17P , additional homework tip  4

Figure 2

The proton Ha gets split into a triplet because it has two adjacent proton, the proton Hb gets split into a quartet by 3Ha protons, the proton Hc gets split into a septet by 6Hd protons and the proton Hd gets split into a doublet by 1Hc proton. The chemical shift of Ha is approximately 1.2 ppm. The chemical shift of Hb is approximately 2.4 ppm. The chemical shift of Hc is approximately 5.0 ppm and the chemical shift of Hd is approximately 1.8 ppm.

Conclusion

The 1H NMR spectrum of the given compound is shown in Figure 2. It gives four signals with three, four, seven and two peaks.

Expert Solution
Check Mark
Interpretation Introduction

(c)

Interpretation:

The 1H NMR spectrum of the given compound is to be described. The number of NMR signals, the splitting pattern for each signal and the approximate chemical shift values are to be stated.

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. On the horizontal axis, the position of absorption is generally referred to as chemical shift.

Answer to Problem 14.17P

The 1H NMR spectrum of the given compound is,

Organic Chemistry-Package(Custom), Chapter 14, Problem 14.17P , additional homework tip  5

The number of NMR signals, the splitting pattern for each signal and the approximate chemical shift values are rightfully stated.

Explanation of Solution

The given compound is 1,3dimethoxypropane(CH3OCH2CH2CH2OCH3). It contains three types of proton Ha, Hb and Hc. Therefore, it gives three signals in 1H NMR spectrum. The 1H NMR spectrum of the given compound is shown below.

Organic Chemistry-Package(Custom), Chapter 14, Problem 14.17P , additional homework tip  6

Figure 3

The proton Ha gets split into a singlet because it has no adjacent proton, the proton Hb gets split into a triplet by 2Hc protons and the proton Hc gets split into a quintet, five peaks by 2+2=4Hb protons. The chemical shift of Ha is approximately 3.3 ppm. The chemical shift of Hb is approximately 3.4 ppm and the chemical shift of Hc is approximately 1.7 ppm.

Conclusion

The 1H NMR spectrum of the given compound is shown in Figure 3. It gives three signals with one, three and five peaks.

Expert Solution
Check Mark
Interpretation Introduction

(d)

Interpretation:

The 1H NMR spectrum of the given compound is to be described. The number of NMR signals, the splitting pattern for each signal and the approximate chemical shift values are to be stated.

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. On the horizontal axis, the position of absorption is generally referred to as chemical shift.

Answer to Problem 14.17P

The 1H NMR spectrum of the given compound is,

Organic Chemistry-Package(Custom), Chapter 14, Problem 14.17P , additional homework tip  7

The number of NMR signals, the splitting pattern for each signal and the approximate chemical shift values are rightfully stated.

Explanation of Solution

The given compound is cis3hexene(CH3CH2CH=CHCH2CH3). It contains three types of proton Ha, Hb and Hc. Therefore, it gives three signals in 1H NMR spectrum. The 1H NMR spectrum of the given compound is shown below.

Organic Chemistry-Package(Custom), Chapter 14, Problem 14.17P , additional homework tip  8

Figure 4

The proton Ha gets split into a triplet because it has two adjacent proton, the proton Hb gets split into a quintet, five peaks by 3+1=4Hc and Hb protons and the proton Hc gets split into a triplet by two Hb protons. The chemical shift of Ha is approximately 5.4 ppm. The chemical shift of Hb is approximately 2.0 ppm and the chemical shift of Hc is approximately 1.1 ppm.

Conclusion

The 1H NMR spectrum of the given compound is shown in Figure 4. It gives three signals with three, five and three peaks.

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Chapter 14 Solutions

Organic Chemistry-Package(Custom)

Ch. 14 - Prob. 14.11PCh. 14 - Prob. 14.12PCh. 14 - Prob. 14.13PCh. 14 - For each compound give the number of 1H NMR...Ch. 14 - Prob. 14.15PCh. 14 - Prob. 14.16PCh. 14 - Describe the 1H NMR spectrum of each compound....Ch. 14 - Draw a splitting diagram for Hb 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 - What protons in alcohol A give rise to each signal...Ch. 14 - How many peaks are observed in the NMR signal for...Ch. 14 - Propose a structure for a compound of molecular...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 - How many lines are observed in the 13C NMR...Ch. 14 - Problem 14.28 Draw all constitutional isomers of...Ch. 14 - Esters of chrysanthemic acid are naturally...Ch. 14 - Prob. 14.29PCh. 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 - How many different types of protons are present in...Ch. 14 - How many 1H NMR signals does each compound give?...Ch. 14 - 14.37 How many NMR signals does each natural...Ch. 14 - Prob. 14.38PCh. 14 - Acetone exhibits a singlet in its 1H NMR spectrum...Ch. 14 - Prob. 14.40PCh. 14 - Prob. 14.41PCh. 14 - How could you use chemical shift and integration...Ch. 14 - Which compounds give one singlet in the 1H NMR...Ch. 14 - Prob. 14.44PCh. 14 - 14.43 How can you use NMR spectroscopy to...Ch. 14 - Prob. 14.46PCh. 14 - Prob. 14.47PCh. 14 - Which compounds in Problem 14.43 give one signal...Ch. 14 - Prob. 14.49PCh. 14 - How many 13C NMR signals does each compound...Ch. 14 - Rank the highlighted carbon atoms in each compound...Ch. 14 - 14.50 Identify the carbon atoms that give rise to...Ch. 14 - 14.51 a. How many signals does dimethyl...Ch. 14 - 14.53 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 - Low molecular weight esters RCO2R often have...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. 14.75PCh. 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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