OWLv2 with MindTap Reader, 1 term (6 months) Printed Access Card for Brown/Iverson/Anslyn/Foote's Organic Chemistry, 8th Edition
OWLv2 with MindTap Reader, 1 term (6 months) Printed Access Card for Brown/Iverson/Anslyn/Foote's Organic Chemistry, 8th Edition
8th Edition
ISBN: 9781305582439
Author: Brown, William H.; Iverson, Brent L.; Anslyn, Eric; Foote, Christopher S.
Publisher: Cengage Learning
Question
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Chapter 17, Problem 17.17P

(a)

Interpretation Introduction

Interpretation:

Structural formula of the compound whose 1H-NMR and 13C-NMR are given, which shows strong absorption between 1720-1700cm-1 and strong broad absorption over the region 2500-3300cm-1 has to be proposed.

Concept-Introduction:

Nuclear Magnetic Resonance Spectroscopy:

Nuclear Magnetic Resonance Spectroscopy or NMR Spectroscopy is a technique used to find the purity, content and molecular structure of the compound.  Resonance transition between energy levels happens if electromagnetic radiation with specific frequency is applied on an atomic nuclei placed in an electromagnetic field.  This transition happens only if the frequency of applied radiation matches with the frequency of magnetic field, then it is to be in resonance condition.  If an external magnetic field is applied spin gets excited from its ground state to the excited state by absorbing energy.  The absorbed radio frequency is emitted back at the same frequency level, when the spin returns to its ground state.  This radio frequency will give the NMR spectra.  The plot of the spectra is between Intensity of the signal VS magnetic field.  Trimethyl Silane ie, TMS is used as the reference.  Chemical shift is a term which refers to the position in the spectrum.  It is dependent on several factors like electron density around the proton, inductive effect etc.

1HNMR:

It is also known as Proton Nuclear Magnetic Resonance.  Hydrogen nuclei with in the molecule is considered here.  1Hydrogen, 2Deuterium, 3Tritium are the three isotopes of hydrogen used in NME spectroscopy.  All the three will have different resonating frequency.  They have different chemical shift also.

13C-NMR:

The NMR signals for the 13C nuclei are weaker than the proton signals.  Because the magnetic moment of 13C is very weak.  It is very difficult to observe the peaks.  The number of signals will give the equivalent set of carbons.

(a)

Expert Solution
Check Mark

Explanation of Solution

Splitting in 1H NMR – n+1, n is the number of adjacent protons.

In 1H NMR, For CH3 the chemical shift will be in the range of 0.9-1.0ppm, CH2, the chemical shift lies in the range of 1.2-1.7ppm.  COOH the value will be 10-13ppm

In 13C-NMR, For CH3 the chemical shift will be in the range of 13-16ppm, CH2, the chemical shift is in the range of 16-25ppm, COOH the value will be in the range of 160-185ppm.

.94ppm will the shift of CH3 group, 1.39 and 1.62 will be the shift of CH2 group, 12.0 will be the shift of COOH, one CH2 is attached to the acid group so, it will have a slight increase in its chemical shift ie, the value is 2.35ppm. So proton NMR matches with the given data

13.69ppm will the shift of CH3 group, 22.21 and 26.76 will be the shift of CH2 group, 180.71 will be the shift of COOH, one CH2 is attached to the acid group so, it will have a slight increase in its chemical shift ie, the value is 33.89ppm. So 13C-NMR matches with the given data.

So the given values of the 1H NMR and 13C-NMR matches with chemical shift ranges of the groups.

Structural formula of the compound is;

OWLv2 with MindTap Reader, 1 term (6 months) Printed Access Card for Brown/Iverson/Anslyn/Foote's Organic Chemistry, 8th Edition, Chapter 17, Problem 17.17P , additional homework tip  1

(b)

Interpretation Introduction

Interpretation:

Structural formula of the compound whose 1H-NMR and 13C-NMR are given, which shows strong absorption between 1720-1700cm-1 and strond broad absorption over the region 2500-3300cm-1 has to be proposed.

Concept-Introduction:

Nuclear Magnetic Resonance Spectroscopy:

Nuclear Magnetic Resonance Spectroscopy or NMR Spectroscopy is a technique used to find the purity, content and molecular structure of the compound.  Resonance transition between energy levels happens if electromagnetic radiation with specific frequency is applied on an atomic nuclei placed in an electromagnetic field.  This transition happens only if the frequency of applied radiation matches with the frequency of magnetic field, then it is to be in resonance condition.  If an external magnetic field is applied spin gets excited from its ground state to the excited state by absorbing energy.  The absorbed radio frequency is emitted back at the same frequency level, when the spin returns to its ground state.  This radio frequency will give the NMR spectra.  The plot of the spectra is between Intensity of the signal VS magnetic field.  Trimethyl Silane ie, TMS is used as the reference.  Chemical shift is a term which refers to the position in the spectrum.  It is dependent on several factors like electron density around the proton, inductive effect etc.

1HNMR:

It is also known as Proton Nuclear Magnetic Resonance.  Hydrogen nuclei with in the molecule is considered here. 1Hydrogen  2Deuterium, 3Tritium are the three isotopes of hydrogen used in NME spectroscopy.  All the three will have different resonating frequency.  They have different chemical shift also.

13CNMR:

The NMR signals for the 13C nuclei are weaker than the proton signals.  Because the magnetic moment of 13C is very weak.  It is very difficult to observe the peaks.  The number of signals will give the equivalent set of carbons.

(b)

Expert Solution
Check Mark

Explanation of Solution

Splitting in 1H NMR – n+1, n is the number of adjacent protons.

In 1H NMR, For CH3 the chemical shift will be in the range of 0.9-1.0ppm, CH2, the chemical shift lies in the range of 1.2-1.7ppm.  COOH the value will be 10-13ppm.

In 13C-NMR, For CH3 the chemical shift will be in the range of 13-16ppm, CH2, the chemical shift is in the range of 16-25ppm, COOH the value will be in the range of 160-185ppm.

1.08ppm will the shift of CH3, 12.1 will be the shift of COOH, one CH2 is attached to the acid group so, it will have a slight increase in its chemical shift ie, the value is 2.23ppm.  Three CH3 groups are attached to carbon which doesn’t have any proton.

30.69ppm will the shift of CH3 group, 179.26 will be the shift of COOH, one CH2 is attached to the acid group so, it will have a slight increase in its chemical shift ie, the value is47.82ppm. So 13C-NMR matches with the given data If the spectrum is given counting the number of signals will more easily predictable.

So the given values of the 1H NMR and 13C-NMR matches with chemical shift ranges of the groups.

Structure formula of the compound is:

OWLv2 with MindTap Reader, 1 term (6 months) Printed Access Card for Brown/Iverson/Anslyn/Foote's Organic Chemistry, 8th Edition, Chapter 17, Problem 17.17P , additional homework tip  2

(c)

Interpretation Introduction

Interpretation:

Structural formula of the compound whose 1H-NMR and 13C-NMR are given, which shows strong absorption between 1720-1700cm-1 and strong broad absorption over the region 2500-3300cm-1 has to be proposed.

Concept-Introduction:

Nuclear Magnetic Resonance Spectroscopy:

Nuclear Magnetic Resonance Spectroscopy or NMR Spectroscopy is a technique used to find the purity, content and molecular structure of the compound.  Resonance transition between energy levels happens if electromagnetic radiation with specific frequency is applied on atomic nuclei placed in an electromagnetic field.  This transition happens only if the frequency of applied radiation matches with the frequency of magnetic field, then it is to be in resonance condition.  If an external magnetic field is applied spin gets excited from its ground state to the excited state by absorbing energy.  The absorbed radio frequency is emitted back at the same frequency level, when the spin returns to its ground state.  This radio frequency will give the NMR spectra.  The plot of the spectra is between Intensity of the signal VS magnetic field.  Trimethyl Silane ie, TMS is used as the reference.  Chemical shift is a term which refers to the position in the spectrum.  It is dependent on several factors like electron density around the proton, inductive effect etc.

1HNMR:

It is also known as Proton Nuclear Magnetic Resonance.  Hydrogen nuclei with in the molecule are considered here.  1Hydrogen, 2Deuterium, 3Tritium are the three isotopes of hydrogen used in NME spectroscopy.  All the three will have different resonating frequency.  They have different chemical shift also.

13CNMR:

The NMR signals for the 13C nuclei are weaker than the proton signals.  Because the magnetic moment of 13C is very weak.  It is very difficult to observe the peaks.  The number Jof signals will give the equivalent set of carbons.

(c)

Expert Solution
Check Mark

Explanation of Solution

Splitting in 1H NMR – n+1, n is the number of adjacent protons.

In 1H NMR, For CH3 the chemical shift will be in the range of 0.9-1.0ppm, CH2, the chemical shift lies in the range of 1.2-1.7ppm. CH the chemical shift in the range of 1.5-2ppm, the chemical shift will be in the range of  COOH the value will be 10-13ppm.

In 13C-NMR, For CH3 the chemical shift will be in the range of 13-16ppm, CH2, the chemical shift is in the range of 16-25ppm, CH the shift will be in the range of 25-30ppm, COOH the value will be in the range of 160-185ppm.

.93ppm will the shift of CH3, 12.7 will be the shift of COOH, CH2 is having a value of 1.80ppm.  3.10ppm is the value of CH group.

11.81ppm will be the shift of CH3 group, 170.94ppm will be the shift of COOH, 21.90ppm will be the shift of CH2, 53.28 is the shift value of CH.  So 13C-NMR matches with the given data.  If the spectrum is given counting the number of signals will more easily predictable.  Here from the formula it is clear that the compound will contain two acid groups ie, dicarboxylic acid.

So the given values of the 1H NMR and 13C-NMR matches with chemical shift ranges of the groups.

Structural formula of the product is;

OWLv2 with MindTap Reader, 1 term (6 months) Printed Access Card for Brown/Iverson/Anslyn/Foote's Organic Chemistry, 8th Edition, Chapter 17, Problem 17.17P , additional homework tip  3

(d)

Interpretation Introduction

Interpretation:

Structural formula of the compound whose 1H-NMR and 13C-NMR are given, which shows strong absorption between 1720-1700cm-1 and strong broad absorption over the region 2500-3300cm-1 has to be proposed.

Concept-Introduction:

Nuclear Magnetic Resonance Spectroscopy:

Nuclear Magnetic Resonance Spectroscopy or NMR Spectroscopy is a technique used to find the purity, content and molecular structure of the compound.  Resonance transition between energy levels happens if electromagnetic radiation with specific frequency is applied on an atomic nuclei placed in an electromagnetic field.  This transition happens only if the frequency of applied radiation matches with the frequency of magnetic field, then it is to be in resonance condition.  If an external magnetic field is applied spin gets excited from its ground state to the excited state by absorbing energy.  The absorbed radio frequency is emitted back at the same frequency level, when the spin returns to its ground state.  This radio frequency will give the NMR spectra.  The plot of the spectra is between Intensity of the signal VS magnetic field.  Trimethyl Silane ie, TMS is used as the reference.  Chemical shift is a term which refers to the position in the spectrum.  It is dependent on several factors like electron density around the proton, inductive effect etc.

1HNMR

It is also known as Proton Nuclear Magnetic Resonance.  Hydrogen nuclei with in the molecule are considered here.  1Hydrogen, 2Deuterium, 3Tritium are the three isotopes of hydrogen used in NME spectroscopy.  All the three will have different resonating frequency.  They have different chemical shift also.

13CNMR

The NMR signals for the 13C nuclei are weaker than the proton signals.  Because the magnetic moment of 13C is very weak.  It is very difficult to observe the peaks.  The number of signals will give the equivalent set of carbons.

(d)

Expert Solution
Check Mark

Explanation of Solution

Splitting in 1H NMR – n+1, n is the number of adjacent protons.

In 1H NMR, For CH3 the chemical shift will be in the range of 0.9-1.0ppm, CH2, the chemical shift lies in the range of 1.2-1.7ppm.  COOH the value will be 10-13ppm.

In 13C-NMR, For CH3 the chemical shift will be in the range of 13-16ppm, CH2, the chemical shift is in the range of 16-25ppm, COOH the value will be in the range of 160-185ppm.

1.29ppm will the shift of CH3 group, 12.8 will be the shift of COOH.  So proton NMR matches with the given data.

22.56ppm will the shift of CH3 group, 174.01ppm will be the shift of COOH.  So 13C-NMR matches with the given data.

So the given values of 1H NMR and 13C-NMR matches with chemical shift ranges of the groups.

OWLv2 with MindTap Reader, 1 term (6 months) Printed Access Card for Brown/Iverson/Anslyn/Foote's Organic Chemistry, 8th Edition, Chapter 17, Problem 17.17P , additional homework tip  4

(e)

Interpretation Introduction

Interpretation:

Structural formula of the compound whose 1H-NMR and 13C-NMR are given, which shows strong absorption between 1720-1700cm-1 and strond broad absorption over the region 2500-3300cm-1 has to be proposed.

Concept-Introduction:

Nuclear Magnetic Resonance Spectroscopy:

Nuclear Magnetic Resonance Spectroscopy or NMR Spectroscopy is a technique used to find the purity, content and molecular structure of the compound.  Resonance transition between energy levels happens if electromagnetic radiation with specific frequency is applied on an atomic nuclei placed in an electromagnetic field.  This transition happens only if the frequency of applied radiation matches with the frequency of magnetic field, then it is to be in resonance condition.  If an external magnetic field is applied spin gets excited from its ground state to the excited state by absorbing energy.  The absorbed radio frequency is emitted back at the same frequency level, when the spin returns to its ground state.  This radio frequency will give the NMR spectra.  The plot of the spectra is between Intensity of the signal VS magnetic field.  Trimethyl Silane ie, TMS is used as the reference.  Chemical shift is a term which refers to the position in the spectrum.  It is dependent on several factors like electron density around the proton, inductive effect etc.

1HNMR:

It is also known as Proton Nuclear Magnetic Resonance.  Hydrogen nuclei with in the molecule are considered here.  1Hydrogen, 2Deuterium, 3Tritium are the three isotopes of hydrogen used in NME spectroscopy.  All the three will have different resonating frequency.  They have different chemical shift also.

13CNMR:

The NMR signals for the 13C nuclei are weaker than the proton signals.  Because the magnetic moment of 13C is very weak.  It is very difficult to observe the peaks.  The number of signals will give the equivalent set of carbons.

(e)

Expert Solution
Check Mark

Explanation of Solution

Splitting in 1H NMR – n+1, n is the number of adjacent protons.

In 1H NMR, For CH3 the chemical shift will be in the range of 0.9-1.0ppm, CH2, the chemical shift lies in the range of 1.2-1.7ppm.  COOH the value will be 10-13ppm

In 13C-NMR, For CH3 the chemical shift will be in the range of 13-16ppm, CH2, the chemical shift is in the range of 16-25ppm, COOH the value will be in the range of 160-185ppm.

1.91ppm will the shift of CH3 group, 12.4, 5.86 and 7.10pp will be shift of CH will be the shift of COOH.  So proton NMR matches with the given data.

18.11ppm will the shift of CH3 group, 172.26ppm will be the shift of COOH,. 122.24 and 147.53So 13C-NMR matches with the given data.  The values will change according to the groups attached to the carbon.

 So the given values of 1H NMR and 13C-NMR matches with chemical shift ranges of the groups.

Structural formula of the product;

OWLv2 with MindTap Reader, 1 term (6 months) Printed Access Card for Brown/Iverson/Anslyn/Foote's Organic Chemistry, 8th Edition, Chapter 17, Problem 17.17P , additional homework tip  5

(f)

Interpretation Introduction

Interpretation:

Structural formula of the compound whose 1H-NMR and 13C-NMR are given, which shows strong absorption between 1720-1700cm-1 and strond broad absorption over the region 2500-3300cm-1 has to be proposed.

Concept-Introduction:

Nuclear Magnetic Resonance Spectroscopy:

Nuclear Magnetic Resonance Spectroscopy or NMR Spectroscopy is a technique used to find the purity, content and molecular structure of the compound.  Resonance transition between energy levels happens if electromagnetic radiation with specific frequency is applied on an atomic nuclei placed in an electromagnetic field.  This transition happens only if the frequency of applied radiation matches with the frequency of magnetic field, then it is to be in resonance condition.  If an external magnetic field is applied spin gets excited from its ground state to the excited state by absorbing energy.  The absorbed radio frequency is emitted back at the same frequency level, when the spin returns to its ground state.  This radio frequency will give the NMR spectra.  The plot of the spectra is between Intensity of the signal VS magnetic field.  Trimethyl Silane ie, TMS is used as the reference.  Chemical shift is a term which refers to the position in the spectrum.  It is dependent on several factors like electron density around the proton, inductive effect etc.

1HNMR:

It is also known as Proton Nuclear Magnetic Resonance.  Hydrogen nuclei with in the molecule are considered here.  1Hydrogen, 2Deuterium, 3Tritium are the three isotopes of hydrogen used in NME spectroscopy.  All the three will have different resonating frequency.  They have different chemical shift also.

13CNMR:

The NMR signals for the 13C nuclei are weaker than the proton signals.  Because the magnetic moment of 13C is very weak.  It is very difficult to observe the peaks.  The number of signals will give the equivalent set of carbons.

(f)

Expert Solution
Check Mark

Explanation of Solution

Splitting in 1H NMR – n+1, n is the number of adjacent protons.

In 1H NMR, For CH3 the chemical shift will be in the range of 0.9-1.0ppm, CH2, the chemical shift lies in the range of 1.2-1.7ppm.  COOH the value will be 10-13ppm.

In 13C-NMR, For CH3 the chemical shift will be in the range of 13-16ppm, CH2, the chemical shift is in the range of 16-25ppm, COOH the value will be in the range of 160-185ppm.

2.34ppm will the shift of CH3 group, 11.3 will be the shift of COOH.  So proton NMR matches with the given data.

34.02ppm will the shift of CH3 group,  171.82ppm will be the shift of COOH,. So 13C-NMR matches with the given data.  Here chlorine is also present.

So the given values of 1H NMR and 13C-NMR matches with chemical shift ranges of the groups.

Structure of the product

OWLv2 with MindTap Reader, 1 term (6 months) Printed Access Card for Brown/Iverson/Anslyn/Foote's Organic Chemistry, 8th Edition, Chapter 17, Problem 17.17P , additional homework tip  6

(g)

Interpretation Introduction

Interpretation:

Structural formula of the compound whose 1H-NMR and 13C-NMR are given, which shows strong absorption between 1720-1700cm-1 and strond broad absorption over the region 2500-3300cm-1 has to be proposed.

Concept-Introduction:

Nuclear Magnetic Resonance Spectroscopy:

Nuclear Magnetic Resonance Spectroscopy or NMR Spectroscopy is a technique used to find the purity, content and molecular structure of the compound.  Resonance transition between energy levels happens if electromagnetic radiation with specific frequency is applied on an atomic nuclei placed in an electromagnetic field.  This transition happens only if the frequency of applied radiation matches with the frequency of magnetic field, then it is to be in resonance condition.  If an external magnetic field is applied spin gets excited from its ground state to the excited state by absorbing energy.  The absorbed radio frequency is emitted back at the same frequency level, when the spin returns to its ground state.  This radio frequency will give the NMR spectra.  The plot of the spectra is between Intensity of the signal VS magnetic field. Trimethyl Silane ie, TMS is used as the reference.  Chemical shift is a term which refers to the position in the spectrum.  It is dependent on several factors like electron density around the proton, inductive effect etc.

1HNMR:

It is also known as Proton Nuclear Magnetic Resonance.  Hydrogen nuclei with in the molecule are considered here.  1Hydrogen, 2Deuterium, 3Tritium are the three isotopes of hydrogen used in NME spectroscopy.  All the three will have different resonating frequency.  They have different chemical shift also.

13CNMR:

The NMR signals for the 13C nuclei are weaker than the proton signals.  Because the magnetic moment of 13C is very weak.  It is very difficult to observe the peaks.  The number of signals will give the equivalent set of carbons.

(g)

Expert Solution
Check Mark

Explanation of Solution

Splitting in 1H NMR – n+1, n is the number of adjacent protons.

In 1H NMR, For CH3 the chemical shift will be in the range of 0.9-1.0ppm, CH2, the chemical shift lies in the range of 1.2-1.7ppm.  COOH the value will be 10-13ppm.

In 13C-NMR, For CH3 the chemical shift will be in the range of 13-16ppm, CH2, the chemical shift is in the range of 16-25ppm, COOH the value will be in the range of 160-185ppm.

1.42ppm will the shift of CH3 group, 6.10ppm will be the shift of CH group, 12.0 will be the shift of COOH, one CH2 is attached to the acid group so, it will have a slight increase in its chemical shift ie, the value is 2.35ppm. So proton NMR matches with the given data.

13.69ppm will the shift of CH3 group, 22.21 and 26.76 will be the shift of CH2 group, 180.71 will be the shift of COOH, one CH2 is attached to the acid group so, it will have a slight increase in its chemical shift ie, the value is 33.89ppm. So 13C-NMR matches with the given data.

So the given values of 1H NMR and 13C-NMR matches with chemical shift ranges of the groups.

OWLv2 with MindTap Reader, 1 term (6 months) Printed Access Card for Brown/Iverson/Anslyn/Foote's Organic Chemistry, 8th Edition, Chapter 17, Problem 17.17P , additional homework tip  7

(h)

Interpretation Introduction

Interpretation:

Structural formula of the compound whose 1H-NMR and 13C-NMR are given, which shows strong absorption between 1720-1700cm-1 and strong broad absorption over the region 2500-3300cm-1 has to be proposed.

Concept-Introduction:

Nuclear Magnetic Resonance Spectroscopy:

Nuclear Magnetic Resonance Spectroscopy or NMR Spectroscopy is a technique used to find the purity, content and molecular structure of the compound.  Resonance transition between energy levels happens if electromagnetic radiation with specific frequency is applied on an atomic nuclei placed in an electromagnetic field.  This transition happens only if the frequency of applied radiation matches with the frequency of magnetic field, then it is to be in resonance condition.  If an external magnetic field is applied spin gets excited from its ground state to the excited state by absorbing energy.  The absorbed radio frequency is emitted back at the same frequency level, when the spin returns to its ground state.  This radio frequency will give the NMR spectra.  The plot of the spectra is between Intensity of the signal VS magnetic field.  Trimethyl Silane ie, TMS is used as the reference.  Chemical shift is a term which refers to the position in the spectrum.  It is dependent on several factors like electron density around the proton, inductive effect etc.

1HNMR:

It is also known as Proton Nuclear Magnetic Resonance.  Hydrogen nuclei with in the molecule are considered here.  1Hydrogen, 2Deuterium, 3Tritium are the three isotopes of hydrogen used in NME spectroscopy.  All the three will have different resonating frequency.  They have different chemical shift also.

13CNMR:

The NMR signals for the 13C nuclei are weaker than the proton signals.  Because the magnetic moment of 13C is very weak.  It is very difficult to observe the peaks.  The number of signals will give the equivalent set of carbons.

(h)

Expert Solution
Check Mark

Explanation of Solution

Splitting in 1H NMR – n+1, n is the number of adjacent protons.

In 1H NMR, For CH3 the chemical shift will be in the range of 0.9-1.0ppm, CH2, the chemical shift lies in the range of 1.2-1.7ppm.  COOH the value will be 10-13ppm.

In 13C-NMR, For CH3 the chemical shift will be in the range of 13-16ppm, CH2, the chemical shift is in the range of 16-25ppm, COOH the value will be in the range of 160-185ppm.

97ppm will the shift of CH3 group, 1.50 and 2.50 will be the shift of CH2 group, 12.1 will be the shift of COOH, 4.25 will be the shift of CH.  So proton NMR matches with the given data.

13.24ppm will the shift of CH3 group, 20.48 and 36.49 will be the shift of CH2 group, 176.36 will be the shift of COOH,45.08 will be the shift of CH So 13C-NMR matches with the given data.

So the given values of 1H NMR and 13C-NMR matches with chemical shift ranges.

Structural formula of the compound is;

OWLv2 with MindTap Reader, 1 term (6 months) Printed Access Card for Brown/Iverson/Anslyn/Foote's Organic Chemistry, 8th Edition, Chapter 17, Problem 17.17P , additional homework tip  8

(i)

Interpretation Introduction

Interpretation:

Structural formula of the compound whose 1H-NMR and 13C-NMR are given, which shows strong absorption between 1720-1700cm-1 and strong broad absorption over the region 2500-3300cm-1 has to be proposed.

Concept-Introduction:

Nuclear Magnetic Resonance Spectroscopy:

Nuclear Magnetic Resonance Spectroscopy or NMR Spectroscopy is a technique used to find the purity, content and molecular structure of the compound.  Resonance transition between energy levels happens if electromagnetic radiation with specific frequency is applied on atomic nuclei placed in an electromagnetic field.  This transition happens only if the frequency of applied radiation matches with the frequency of magnetic field, then it is to be in resonance condition.  If an external magnetic field is applied spin gets excited from its ground state to the excited state by absorbing energy.  The absorbed radio frequency is emitted back at the same frequency level, when the spin returns to its ground state.  This radio frequency will give the NMR spectra.  The plot of the spectra is between Intensity of the signal VS magnetic field.  Trimethyl Silane ie, TMS is used as the reference.  Chemical shift is a term which refers to the position in the spectrum.  It is dependent on several factors like electron density around the proton, inductive effect etc.

1HNMR:

It is also known as Proton Nuclear Magnetic Resonance.  A hydrogen nucleus with in the molecule is considered here.  1Hydrogen, 2Deuterium, 3Tritium are the three isotopes of hydrogen used in NME spectroscopy.  All the three will have different resonating frequency.  They have different chemical shift also.

13CNMR:

The NMR signals for the 13C nuclei are weaker than the proton signals.  Because the magnetic moment of 13C is very weak.  It is very difficult to observe the peaks.  The number of signals will give the equivalent set of carbons.

(i)

Expert Solution
Check Mark

Explanation of Solution

Splitting in 1H NMR – n+1, n is the number of adjacent protons.

In 1H NMR, For CH3 the chemical shift will be in the range of 0.9-1.0ppm, CH2, the chemical shift lies in the range of 1.2-1.7ppm.  COOH the value will be 10-13ppm.

In 13C-NMR, For CH3 the chemical shift will be in the range of 13-16ppm, CH2, the chemical shift is in the range of 16-25ppm, COOH the value will be in the range of 160-185ppm.

3.38ppm will the shift of CH3 group, because it is attached to an oxygen, so the chemical shift will increase.  3.68 and 2.62 will be the shift of CH2 group, here also the chemical shift of CH2 is increased due to the oxygen attachment.  11.5 will be the shift of COOH.  So proton NMR matches with the given data.

34.75ppm will the shift of CH3 group, 58.72 and 67.55 will be the shift of CH2 group, 177.33 will be the shift of COOH.  So 13C-NMR matches with the given data.

So the given values of 1H NMR and 13C-NMR matches with chemical shift ranges of the groups.

So the structure of the product is;

OWLv2 with MindTap Reader, 1 term (6 months) Printed Access Card for Brown/Iverson/Anslyn/Foote's Organic Chemistry, 8th Edition, Chapter 17, Problem 17.17P , additional homework tip  9

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Chapter 17 Solutions

OWLv2 with MindTap Reader, 1 term (6 months) Printed Access Card for Brown/Iverson/Anslyn/Foote's Organic Chemistry, 8th Edition

Ch. 17 - Write the IUPAC name of each compound, showing...Ch. 17 - Prob. 17.8PCh. 17 - Prob. 17.9PCh. 17 - Prob. 17.10PCh. 17 - Prob. 17.11PCh. 17 - Prob. 17.12PCh. 17 - Prob. 17.13PCh. 17 - On a cyclohexane ring, an axial carboxyl group has...Ch. 17 - Prob. 17.15PCh. 17 - Prob. 17.16PCh. 17 - Prob. 17.17PCh. 17 - Complete each reaction.Ch. 17 - Prob. 17.19PCh. 17 - Prob. 17.20PCh. 17 - Prob. 17.21PCh. 17 - Show the reagents and experimental conditions...Ch. 17 - Prob. 17.23PCh. 17 - Prob. 17.24PCh. 17 - Prob. 17.25PCh. 17 - In each set, assign the acid its appropriate pKa.Ch. 17 - Low-molecular-weight dicarboxylic acids normally...Ch. 17 - Complete the following acid-base reactions. (a)...Ch. 17 - Prob. 17.29PCh. 17 - Prob. 17.30PCh. 17 - Excess ascorbic acid is excreted in the urine, the...Ch. 17 - Give the expected organic product when...Ch. 17 - Show how to convert trans-3-phenyl-2-propenoic...Ch. 17 - Show how to convert 3-oxobutanoic acid...Ch. 17 - Prob. 17.35PCh. 17 - Prob. 17.36PCh. 17 - Prob. 17.37PCh. 17 - When 4-hydroxybutanoic acid is treated with an...Ch. 17 - Fischer esterification cannot be used to prepare...Ch. 17 - Draw the product formed on thermal decarboxylation...Ch. 17 - Prob. 17.41PCh. 17 - Show how cyclohexanecarboxylic acid could be...Ch. 17 - Prob. 17.43PCh. 17 - Prob. 17.44PCh. 17 - Prob. 17.45PCh. 17 - Write the products of the following sequences of...Ch. 17 - Using your reaction roadmaps as a guide, show how...Ch. 17 - Using your reaction roadmaps as a guide, show how...Ch. 17 - Using your reaction roadmaps as a guide, show how...Ch. 17 - Using your reaction roadmaps as a guide, show how...Ch. 17 - Prob. 17.51PCh. 17 - Complete the following Fischer esterification...Ch. 17 - Prob. 17.53P
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