Organic Chemistry
Organic Chemistry
7th Edition
ISBN: 9780321803221
Author: Paula Y. Bruice
Publisher: Prentice Hall
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Chapter 15, Problem 52P

(a)

Interpretation Introduction

Interpretation:

The relationship between the given parameters has to be determined.

Concept introduction:

The NMR spectrum of any compound is taken with reference to a standard compound called reference compound.  Generally, tetramethylsilane (TMS) is taken as the reference compound.  The methyl protons of TMS are equivalent and produces only one sharp peak at the rightmost end of the scale.

The distance between the TMS signal and the signals produced by the compound is called the chemical shift.  Chemical shift basically measures the shift in the signal position of the compound with respect to the reference signal.

Chemical shift in delta scale is given as,

Chemical shift=Distance from the TMS signalOperating frequency of the spectrometer

The value of the chemical shift can be either in ppm or in Hertz.

The distance between the adjacent peaks obtained from the splitting of an NMR signal is known as coupling constant.  It is denoted by J and is measured in Hertz.  Coupling constant is useful when the interpretation of a complex NMR spectrum has to be done.

(b)

Interpretation Introduction

Interpretation:

The relationship between the given parameters has to be determined.

Concept introduction:

The NMR spectrum of any compound is taken with reference to a standard compound called reference compound.  Generally, tetramethylsilane (TMS) is taken as the reference compound.  The methyl protons of TMS are equivalent and produces only one sharp peak at the rightmost end of the scale.

The distance between the TMS signal and the signals produced by the compound is called the chemical shift.  Chemical shift basically measures the shift in the signal position of the compound with respect to the reference signal.

Chemical shift in delta scale is given as,

Chemical shift=Distance from the TMS signalOperating frequency of the spectrometer

The value of the chemical shift can be either in ppm or in Hertz.

The distance between the adjacent peaks obtained from the splitting of an NMR signal is known as coupling constant.  It is denoted by J and is measured in Hertz.  Coupling constant is useful when the interpretation of a complex NMR spectrum has to be done.

(c)

Interpretation Introduction

Interpretation:

The relationship between the given parameters has to be determined.

Concept introduction:

The NMR spectrum of any compound is taken with reference to a standard compound called reference compound.  Generally, tetramethylsilane (TMS) is taken as the reference compound.  The methyl protons of TMS are equivalent and produces only one sharp peak at the rightmost end of the scale.

The distance between the TMS signal and the signals produced by the compound is called the chemical shift. Chemical shift basically measures the shift in the signal position of the compound with respect to the reference signal.

Chemical shift in delta scale is given as,

Chemical shift=Distance from the TMS signalOperating frequency of the spectrometer

The value of the chemical shift can be either in ppm or in Hertz.

The distance between the adjacent peaks obtained from the splitting of an NMR signal is known as coupling constant.  It is denoted by J and is measured in Hertz.  Coupling constant is useful when the interpretation of a complex NMR spectrum has to be done.

(d)

Interpretation Introduction

Interpretation:

The relationship between the given parameters has to be determined.

Concept introduction:

The NMR spectrum of any compound is taken with reference to a standard compound called reference compound.  Generally, tetramethylsilane (TMS) is taken as the reference compound.  The methyl protons of TMS are equivalent and produces only one sharp peak at the rightmost end of the scale.

The distance between the TMS signal and the signals produced by the compound is called the chemical shift. Chemical shift basically measures the shift in the signal position of the compound with respect to the reference signal.

Chemical shift in delta scale is given as,

Chemical shift=Distance from the TMS signalOperating frequency of the spectrometer

The value of the chemical shift can be either in ppm or in Hertz.

The distance between the adjacent peaks obtained from the splitting of an NMR signal is known as coupling constant.  It is denoted by J and is measured in Hertz.  Coupling constant is useful when the interpretation of a complex NMR spectrum has to be done.

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Answer the following questions: a. What is the relationship between chemical shift in ppm and operating frequency? b. What is the relationship between chemical shift in hertz and operating frequency? c. What is the relationship between coupling constant in hertz and operating frequency? d. How does the operating frequency in NMR spectroscopy compare with the operating frequency in IR and UV/Vis spectroscopy?
How does the operating frequency in NMR spectroscopy compare with the operating frequency in IR and UV/Vis spectroscopy?
Provide one advantage of the additional alternative Infrared (IR) Spectroscopy method over the IR method.

Chapter 15 Solutions

Organic Chemistry

Ch. 15.6 - Prob. 11PCh. 15.7 - Prob. 12PCh. 15.7 - Prob. 13PCh. 15.7 - Without referring to Table 14.1, label the proton...Ch. 15.8 - [18]-Annulene shows two signals in its 1H NMR...Ch. 15.9 - How would integration distinguish the 1H NMR...Ch. 15.9 - Which of the following compounds is responsible...Ch. 15.10 - Prob. 19PCh. 15.10 - Explain how the following compounds, each with the...Ch. 15.10 - The 1H NMR spectra of two carboxylic acids with...Ch. 15.11 - Draw a diagram like the one shown in Figure 14.12...Ch. 15.12 - Indicate the number of signals and the...Ch. 15.12 - How can their 1H NMR spectra distinguish the...Ch. 15.12 - Identify each compound from its molecular formula...Ch. 15.12 - Prob. 27PCh. 15.12 - Propose structures that are consistent with the...Ch. 15.12 - Describe the 1H NMR spectrum you would expect for...Ch. 15.13 - Prob. 30PCh. 15.13 - Identify the compound with molecular formula...Ch. 15.14 - Prob. 32PCh. 15.15 - a. For the following compounds, which pairs of...Ch. 15.17 - Explain why the chemical shift of the OH proton of...Ch. 15.17 - Prob. 37PCh. 15.17 - Prob. 38PCh. 15.17 - Prob. 39PCh. 15.20 - Answer the following questions for each compound:...Ch. 15.20 - Prob. 41PCh. 15.20 - How can 1,2-, 1,3-, and 1,4-dinitrobenzene be...Ch. 15.20 - Identify each compound below from its molecular...Ch. 15.22 - Prob. 44PCh. 15.22 - What does cross peak X in Figure 14.34 tell you?Ch. 15 - Prob. 46PCh. 15 - Draw a spitting diagram for the Hb proton and give...Ch. 15 - Label each set of chemically equivalent protons,...Ch. 15 - Match each of the 1H NMR spectra with one of the...Ch. 15 - Determine the ratios of the chemically...Ch. 15 - How can 1H NMR distinguish between the compounds...Ch. 15 - Prob. 52PCh. 15 - The 1H NMR spectra of three isomers with molecular...Ch. 15 - Prob. 54PCh. 15 - Prob. 55PCh. 15 - Prob. 56PCh. 15 - Compound A, with molecular formula C4H9Cl, shows...Ch. 15 - The 1H NMR spectra of three isomers with molecular...Ch. 15 - Would it be better to use 1H NMR or 13C NMR...Ch. 15 - There are four esters with molecular formula...Ch. 15 - An alkyl halide reacts with an alkoxide ion to...Ch. 15 - Identity each of the following compounds from its...Ch. 15 - Identity each of the following compounds from its...Ch. 15 - Prob. 64PCh. 15 - How can the signals in the 6.5 to 8.1 ppm region...Ch. 15 - The 1H NMR spectra of two compounds, each with...Ch. 15 - Draw a splitting diagram for the Hb proton if Jbc...Ch. 15 - Sketch the following spectra that would be...Ch. 15 - How can 1H NMR be used to prove that the addition...Ch. 15 - Identity each of the following compounds from its...Ch. 15 - Dr. N. M. Arr was called in to help analyze the 1H...Ch. 15 - Calculate the amount of energy (in calories)...Ch. 15 - The following 1H NMR spectra are four compounds,...Ch. 15 - When compound A (C5H12O) is treated with HBr, it...Ch. 15 - Identity each of the following compounds from its...Ch. 15 - Identify each of the following compounds from its...Ch. 15 - Identity the compound with molecular formula...Ch. 15 - Identify the compound with molecular formula C6H14...
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