Chapter 17, Problem 17.17P

(a)

Interpretation Introduction

Interpretation:

Structural formula of the compound whose ${}^{\text{1}}\text{H-NMR}$ and ${}^{\text{13}}\text{C-NMR}$ are given, which shows strong absorption between ${\text{1720-1700cm}}^{\text{-1}}$ and strong broad absorption over the region ${\text{2500-3300cm}}^{\text{-1}}$ 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.

${}^{\text{1}}\text{H}$NMR:

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

${}^{\text{13}}\text{C}$-NMR:

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

Explanation of Solution

Splitting in ${}^{\text{1}}\text{H}$ NMR – n+1, n is the number of adjacent protons.

In ${}^{\text{1}}\text{H}$ NMR, For ${\text{CH}}_{\text{3}}$ the chemical shift will be in the range of 0.9-1.0ppm, ${\text{CH}}_2$, the chemical shift lies in the range of 1.2-1.7ppm.  $\text{COOH}$ the value will be 10-13ppm

In ${}^{\text{13}}\text{C}$-NMR, For ${\text{CH}}_{\text{3}}$ the chemical shift will be in the range of 13-16ppm, ${\text{CH}}_2$, the chemical shift is in the range of 16-25ppm, $\text{COOH}$ the value will be in the range of 160-185ppm.

.94ppm will the shift of ${\text{CH}}_{\text{3}}$ group, 1.39 and 1.62 will be the shift of ${\text{CH}}_2$ group, 12.0 will be the shift of $\text{COOH}$, one ${\text{CH}}_2$ 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 ${\text{CH}}_{\text{3}}$ group, 22.21 and 26.76 will be the shift of ${\text{CH}}_2$ group, 180.71 will be the shift of $\text{COOH}$, one ${\text{CH}}_2$ is attached to the acid group so, it will have a slight increase in its chemical shift ie, the value is 33.89ppm. So ${}^{\text{13}}\text{C}$-NMR matches with the given data.

So the given values of the ${}^{\text{1}}\text{H}$ NMR and ${}^{\text{13}}\text{C}$-NMR matches with chemical shift ranges of the groups.

Structural formula of the compound is;

(b)

Interpretation Introduction

Interpretation:

Structural formula of the compound whose ${}^{\text{1}}\text{H-NMR}$ and ${}^{\text{13}}\text{C-NMR}$ are given, which shows strong absorption between ${\text{1720-1700cm}}^{\text{-1}}$ and strond broad absorption over the region ${\text{2500-3300cm}}^{\text{-1}}$ 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.

${}^{\text{1}}\text{H}$NMR:

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

${}^{\text{13}}\text{C}$NMR:

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

Explanation of Solution

Splitting in ${}^{\text{1}}\text{H}$ NMR – n+1, n is the number of adjacent protons.

In ${}^{\text{1}}\text{H}$ NMR, For ${\text{CH}}_{\text{3}}$ the chemical shift will be in the range of 0.9-1.0ppm, ${\text{CH}}_2$, the chemical shift lies in the range of 1.2-1.7ppm.  $\text{COOH}$ the value will be 10-13ppm.

In ${}^{\text{13}}\text{C}$-NMR, For ${\text{CH}}_{\text{3}}$ the chemical shift will be in the range of 13-16ppm, ${\text{CH}}_2$, the chemical shift is in the range of 16-25ppm, $\text{COOH}$ the value will be in the range of 160-185ppm.

1.08ppm will the shift of ${\text{CH}}_{\text{3}}$, 12.1 will be the shift of $\text{COOH}$, one ${\text{CH}}_2$ is attached to the acid group so, it will have a slight increase in its chemical shift ie, the value is 2.23ppm.  Three ${\text{CH}}_{\text{3}}$ groups are attached to carbon which doesn’t have any proton.

30.69ppm will the shift of ${\text{CH}}_{\text{3}}$ group, 179.26 will be the shift of $\text{COOH}$, one ${\text{CH}}_2$ is attached to the acid group so, it will have a slight increase in its chemical shift ie, the value is47.82ppm. So ${}^{\text{13}}\text{C}$-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 ${}^{\text{1}}\text{H}$ NMR and ${}^{\text{13}}\text{C}$-NMR matches with chemical shift ranges of the groups.

Structure formula of the compound is:

(c)

Interpretation Introduction

Interpretation:

Structural formula of the compound whose ${}^{\text{1}}\text{H-NMR}$ and ${}^{\text{13}}\text{C-NMR}$ are given, which shows strong absorption between ${\text{1720-1700cm}}^{\text{-1}}$ and strong broad absorption over the region ${\text{2500-3300cm}}^{\text{-1}}$ 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.

${}^{\text{1}}\text{H}$NMR:

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

${}^{\text{13}}\text{C}$NMR:

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

Explanation of Solution

Splitting in ${}^{\text{1}}\text{H}$ NMR – n+1, n is the number of adjacent protons.

In ${}^{\text{1}}\text{H}$ NMR, For ${\text{CH}}_{\text{3}}$ the chemical shift will be in the range of 0.9-1.0ppm, ${\text{CH}}_2$, the chemical shift lies in the range of 1.2-1.7ppm. $\text{CH}$ the chemical shift in the range of 1.5-2ppm, the chemical shift will be in the range of  $\text{COOH}$ the value will be 10-13ppm.

In ${}^{\text{13}}\text{C}$-NMR, For ${\text{CH}}_{\text{3}}$ the chemical shift will be in the range of 13-16ppm, ${\text{CH}}_2$, the chemical shift is in the range of 16-25ppm, $\text{CH}$ the shift will be in the range of 25-30ppm, $\text{COOH}$ the value will be in the range of 160-185ppm.

.93ppm will the shift of ${\text{CH}}_{\text{3}}$, 12.7 will be the shift of $\text{COOH}$, ${\text{CH}}_2$ is having a value of 1.80ppm.  3.10ppm is the value of $\text{CH}$ group.

11.81ppm will be the shift of ${\text{CH}}_{\text{3}}$ group, 170.94ppm will be the shift of $\text{COOH}$, 21.90ppm will be the shift of ${\text{CH}}_2$, 53.28 is the shift value of $\text{CH}$.  So ${}^{\text{13}}\text{C}$-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 ${}^{\text{1}}\text{H}$ NMR and ${}^{\text{13}}\text{C}$-NMR matches with chemical shift ranges of the groups.

Structural formula of the product is;

(d)

Interpretation Introduction

Interpretation:

Structural formula of the compound whose ${}^{\text{1}}\text{H-NMR}$ and ${}^{\text{13}}\text{C-NMR}$ are given, which shows strong absorption between ${\text{1720-1700cm}}^{\text{-1}}$ and strong broad absorption over the region ${\text{2500-3300cm}}^{\text{-1}}$ 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.

${}^{\text{1}}\text{H}$NMR

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

${}^{\text{13}}\text{C}$NMR

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

Explanation of Solution

Splitting in ${}^{\text{1}}\text{H}$ NMR – n+1, n is the number of adjacent protons.

In ${}^{\text{1}}\text{H}$ NMR, For ${\text{CH}}_{\text{3}}$ the chemical shift will be in the range of 0.9-1.0ppm, ${\text{CH}}_2$, the chemical shift lies in the range of 1.2-1.7ppm.  $\text{COOH}$ the value will be 10-13ppm.

In ${}^{\text{13}}\text{C}$-NMR, For ${\text{CH}}_{\text{3}}$ the chemical shift will be in the range of 13-16ppm, ${\text{CH}}_2$, the chemical shift is in the range of 16-25ppm, $\text{COOH}$ the value will be in the range of 160-185ppm.

1.29ppm will the shift of ${\text{CH}}_{\text{3}}$ group, 12.8 will be the shift of $\text{COOH}$.  So proton NMR matches with the given data.

22.56ppm will the shift of ${\text{CH}}_{\text{3}}$ group, 174.01ppm will be the shift of $\text{COOH}$.  So ${}^{\text{13}}\text{C}$-NMR matches with the given data.

So the given values of ${}^{\text{1}}\text{H}$ NMR and ${}^{\text{13}}\text{C}$-NMR matches with chemical shift ranges of the groups.

(e)

Interpretation Introduction

Interpretation:

Structural formula of the compound whose ${}^{\text{1}}\text{H-NMR}$ and ${}^{\text{13}}\text{C-NMR}$ are given, which shows strong absorption between ${\text{1720-1700cm}}^{\text{-1}}$ and strond broad absorption over the region ${\text{2500-3300cm}}^{\text{-1}}$ 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.

${}^{\text{1}}\text{H}$NMR:

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

${}^{\text{13}}\text{C}$NMR:

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

Explanation of Solution

Splitting in ${}^{\text{1}}\text{H}$ NMR – n+1, n is the number of adjacent protons.

In ${}^{\text{1}}\text{H}$ NMR, For ${\text{CH}}_{\text{3}}$ the chemical shift will be in the range of 0.9-1.0ppm, ${\text{CH}}_2$, the chemical shift lies in the range of 1.2-1.7ppm.  $\text{COOH}$ the value will be 10-13ppm

In ${}^{\text{13}}\text{C}$-NMR, For ${\text{CH}}_{\text{3}}$ the chemical shift will be in the range of 13-16ppm, ${\text{CH}}_2$, the chemical shift is in the range of 16-25ppm, $\text{COOH}$ the value will be in the range of 160-185ppm.

1.91ppm will the shift of ${\text{CH}}_{\text{3}}$ group, 12.4, 5.86 and 7.10pp will be shift of $\text{CH}$ will be the shift of $\text{COOH}$.  So proton NMR matches with the given data.

18.11ppm will the shift of ${\text{CH}}_{\text{3}}$ group, 172.26ppm will be the shift of $\text{COOH}$,. 122.24 and 147.53So ${}^{\text{13}}\text{C}$-NMR matches with the given data.  The values will change according to the groups attached to the carbon.

 So the given values of ${}^{\text{1}}\text{H}$ NMR and ${}^{\text{13}}\text{C}$-NMR matches with chemical shift ranges of the groups.

Structural formula of the product;

(f)

Interpretation Introduction

Interpretation:

Structural formula of the compound whose ${}^{\text{1}}\text{H-NMR}$ and ${}^{\text{13}}\text{C-NMR}$ are given, which shows strong absorption between ${\text{1720-1700cm}}^{\text{-1}}$ and strond broad absorption over the region ${\text{2500-3300cm}}^{\text{-1}}$ 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.

${}^{\text{1}}\text{H}$NMR:

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

${}^{\text{13}}\text{C}$NMR:

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

Explanation of Solution

Splitting in ${}^{\text{1}}\text{H}$ NMR – n+1, n is the number of adjacent protons.

In ${}^{\text{1}}\text{H}$ NMR, For ${\text{CH}}_{\text{3}}$ the chemical shift will be in the range of 0.9-1.0ppm, ${\text{CH}}_2$, the chemical shift lies in the range of 1.2-1.7ppm.  $\text{COOH}$ the value will be 10-13ppm.

In ${}^{\text{13}}\text{C}$-NMR, For ${\text{CH}}_{\text{3}}$ the chemical shift will be in the range of 13-16ppm, ${\text{CH}}_2$, the chemical shift is in the range of 16-25ppm, $\text{COOH}$ the value will be in the range of 160-185ppm.

2.34ppm will the shift of ${\text{CH}}_{\text{3}}$ group, 11.3 will be the shift of $\text{COOH}$.  So proton NMR matches with the given data.

34.02ppm will the shift of ${\text{CH}}_{\text{3}}$ group,  171.82ppm will be the shift of $\text{COOH}$,. So ${}^{\text{13}}\text{C}$-NMR matches with the given data.  Here chlorine is also present.

So the given values of ${}^{\text{1}}\text{H}$ NMR and ${}^{\text{13}}\text{C}$-NMR matches with chemical shift ranges of the groups.

Structure of the product

(g)

Interpretation Introduction

Interpretation:

Structural formula of the compound whose ${}^{\text{1}}\text{H-NMR}$ and ${}^{\text{13}}\text{C-NMR}$ are given, which shows strong absorption between ${\text{1720-1700cm}}^{\text{-1}}$ and strond broad absorption over the region ${\text{2500-3300cm}}^{\text{-1}}$ 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.

${}^{\text{1}}\text{H}$NMR:

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

${}^{\text{13}}\text{C}$NMR:

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

Explanation of Solution

Splitting in ${}^{\text{1}}\text{H}$ NMR – n+1, n is the number of adjacent protons.

In ${}^{\text{1}}\text{H}$ NMR, For ${\text{CH}}_{\text{3}}$ the chemical shift will be in the range of 0.9-1.0ppm, ${\text{CH}}_2$, the chemical shift lies in the range of 1.2-1.7ppm.  $\text{COOH}$ the value will be 10-13ppm.

In ${}^{\text{13}}\text{C}$-NMR, For ${\text{CH}}_{\text{3}}$ the chemical shift will be in the range of 13-16ppm, ${\text{CH}}_2$, the chemical shift is in the range of 16-25ppm, $\text{COOH}$ the value will be in the range of 160-185ppm.

1.42ppm will the shift of ${\text{CH}}_{\text{3}}$ group, 6.10ppm will be the shift of $\text{CH}$ group, 12.0 will be the shift of $\text{COOH}$, one ${\text{CH}}_2$ 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 ${\text{CH}}_{\text{3}}$ group, 22.21 and 26.76 will be the shift of ${\text{CH}}_2$ group, 180.71 will be the shift of $\text{COOH}$, one ${\text{CH}}_2$ is attached to the acid group so, it will have a slight increase in its chemical shift ie, the value is 33.89ppm. So ${}^{\text{13}}\text{C}$-NMR matches with the given data.

So the given values of ${}^{\text{1}}\text{H}$ NMR and ${}^{\text{13}}\text{C}$-NMR matches with chemical shift ranges of the groups.

(h)

Interpretation Introduction

Interpretation:

Structural formula of the compound whose ${}^{\text{1}}\text{H-NMR}$ and ${}^{\text{13}}\text{C-NMR}$ are given, which shows strong absorption between ${\text{1720-1700cm}}^{\text{-1}}$ and strong broad absorption over the region ${\text{2500-3300cm}}^{\text{-1}}$ 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.

${}^{\text{1}}\text{H}$NMR:

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

${}^{\text{13}}\text{C}$NMR:

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

Explanation of Solution

Splitting in ${}^{\text{1}}\text{H}$ NMR – n+1, n is the number of adjacent protons.

In ${}^{\text{1}}\text{H}$ NMR, For ${\text{CH}}_{\text{3}}$ the chemical shift will be in the range of 0.9-1.0ppm, ${\text{CH}}_2$, the chemical shift lies in the range of 1.2-1.7ppm.  $\text{COOH}$ the value will be 10-13ppm.

In ${}^{\text{13}}\text{C}$-NMR, For ${\text{CH}}_{\text{3}}$ the chemical shift will be in the range of 13-16ppm, ${\text{CH}}_2$, the chemical shift is in the range of 16-25ppm, $\text{COOH}$ the value will be in the range of 160-185ppm.

97ppm will the shift of ${\text{CH}}_{\text{3}}$ group, 1.50 and 2.50 will be the shift of ${\text{CH}}_2$ group, 12.1 will be the shift of $\text{COOH}$, 4.25 will be the shift of $\text{CH}$.  So proton NMR matches with the given data.

13.24ppm will the shift of ${\text{CH}}_{\text{3}}$ group, 20.48 and 36.49 will be the shift of ${\text{CH}}_2$ group, 176.36 will be the shift of $\text{COOH}$,45.08 will be the shift of $\text{CH}$ So ${}^{\text{13}}\text{C}$-NMR matches with the given data.

So the given values of ${}^{\text{1}}\text{H}$ NMR and ${}^{\text{13}}\text{C}$-NMR matches with chemical shift ranges.

Structural formula of the compound is;

(i)

Interpretation Introduction

Interpretation:

Structural formula of the compound whose ${}^{\text{1}}\text{H-NMR}$ and ${}^{\text{13}}\text{C-NMR}$ are given, which shows strong absorption between ${\text{1720-1700cm}}^{\text{-1}}$ and strong broad absorption over the region ${\text{2500-3300cm}}^{\text{-1}}$ 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.

${}^{\text{1}}\text{H}$NMR:

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

${}^{\text{13}}\text{C}$NMR:

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

Explanation of Solution

Splitting in ${}^{\text{1}}\text{H}$ NMR – n+1, n is the number of adjacent protons.

In ${}^{\text{1}}\text{H}$ NMR, For ${\text{CH}}_{\text{3}}$ the chemical shift will be in the range of 0.9-1.0ppm, ${\text{CH}}_2$, the chemical shift lies in the range of 1.2-1.7ppm.  $\text{COOH}$ the value will be 10-13ppm.

In ${}^{\text{13}}\text{C}$-NMR, For ${\text{CH}}_{\text{3}}$ the chemical shift will be in the range of 13-16ppm, ${\text{CH}}_2$, the chemical shift is in the range of 16-25ppm, $\text{COOH}$ the value will be in the range of 160-185ppm.

3.38ppm will the shift of ${\text{CH}}_{\text{3}}$ group, because it is attached to an oxygen, so the chemical shift will increase.  3.68 and 2.62 will be the shift of ${\text{CH}}_2$ group, here also the chemical shift of ${\text{CH}}_2$ is increased due to the oxygen attachment.  11.5 will be the shift of $\text{COOH}$.  So proton NMR matches with the given data.

34.75ppm will the shift of ${\text{CH}}_{\text{3}}$ group, 58.72 and 67.55 will be the shift of ${\text{CH}}_2$ group, 177.33 will be the shift of $\text{COOH}$.  So ${}^{\text{13}}\text{C}$-NMR matches with the given data.

So the given values of ${}^{\text{1}}\text{H}$ NMR and ${}^{\text{13}}\text{C}$-NMR matches with chemical shift ranges of the groups.

So the structure of the product is;