Structure 3.2.10—Proton nuclear magnetic resonance spectroscopy (1H NMR) gives information on the different chemical environments of hydrogen atoms in a molecule. Interpret 1H NMR spectra to deduce the structures of organic molecules from the number of signals, the chemical shifts, and the relative areas under signals (integration traces).

Which organic compound has the ¹H NMR shown?

^{Source: Spectral Database for Organic Compounds, SDBS, n.d. [online] Available at:
https://sdbs.db.aist.go.jp/sdbs/cgi-bin/direct_frame_top.cgi [Accessed 6 October 2021].}

A.  Methanal

B.  Ethanoic acid

C.  Methyl ethanoate

D.  Propanoic acid

Which organic compound has the ¹H NMR shown?

^{Source: Spectral Database for Organic Compounds, SDBS, n.d. [online] Available at:
https://sdbs.db.aist.go.jp/sdbs/cgi-bin/direct_frame_top.cgi [Accessed 6 October 2021].}

A.  Methanal

B.  Ethanoic acid

C.  Methyl ethanoate

D.  Propanoic acid

State the number of ¹H NMR signals for this isomer of xylene and the ratio in which they appear.

State the number of ¹H NMR signals for this isomer of xylene and the ratio in which they appear.

State the number of ¹H NMR signals for this isomer of xylene and the ratio in which they appear.

State the number of ¹H NMR signals for this isomer of xylene and the ratio in which they appear.

State the number of ¹H NMR signals for this isomer of xylene and the ratio in which they appear.

State the number of ¹H NMR signals for this isomer of xylene and the ratio in which they appear.

State the number of 1H NMR signals for this isomer of xylene and the ratio in which they appear.

Number of signals:

Ratio:

State the number of 1H NMR signals for this isomer of xylene and the ratio in which they appear.

Number of signals:

Ratio:

State the number of 1H NMR signals for this isomer of xylene and the ratio in which they appear.

Number of signals:

Ratio:

State the number of 1H NMR signals for this isomer of xylene and the ratio in which they appear.

Number of signals:

Ratio:

State the number of 1H NMR signals for this isomer of xylene and the ratio in which they appear.

Number of signals:

Ratio:

State the number of 1H NMR signals for this isomer of xylene and the ratio in which they appear.

Number of signals:

Ratio:

Which is the ¹H NMR spectrum of tetramethylsilane, TMS, (CH₃)₄Si?

Which is the ¹H NMR spectrum of tetramethylsilane, TMS, (CH₃)₄Si?

Which is the ¹H NMR spectrum of tetramethylsilane, TMS, (CH₃)₄Si?

Which is the ¹H NMR spectrum of tetramethylsilane, TMS, (CH₃)₄Si?

Which compound with the molecular formula ${\mathrm{C}}_4{\mathrm{H}}_8\mathrm{O}$ has this high resolution ${}_1\mathrm{H} \mathrm{NMR}$?

From: libretexts.org. Courtesy of Chris Schaller, Professor (Chemistry)
at College of Saint Benedict/Saint John’s University.

A.  but-3-en-2-ol, ${\mathrm{CH}}_2=\mathrm{CHCH}\left(\mathrm{OH}\right){\mathrm{CH}}_3$

B.  butanal, ${\mathrm{CH}}_3{\mathrm{CH}}_2{\mathrm{CH}}_2\mathrm{CHO}$

C.  butanone, ${\mathrm{CH}}_3{\mathrm{COCH}}_2{\mathrm{CH}}_3$

D.  but-3-en-1-ol, ${\mathrm{CH}}_2={\mathrm{CHCH}}_2{\mathrm{CH}}_2\mathrm{OH}$

Which compound with the molecular formula ${\mathrm{C}}_4{\mathrm{H}}_8\mathrm{O}$ has this high resolution ${}_1\mathrm{H} \mathrm{NMR}$?

From: libretexts.org. Courtesy of Chris Schaller, Professor (Chemistry)
at College of Saint Benedict/Saint John’s University.

A.  but-3-en-2-ol, ${\mathrm{CH}}_2=\mathrm{CHCH}\left(\mathrm{OH}\right){\mathrm{CH}}_3$

B.  butanal, ${\mathrm{CH}}_3{\mathrm{CH}}_2{\mathrm{CH}}_2\mathrm{CHO}$

C.  butanone, ${\mathrm{CH}}_3{\mathrm{COCH}}_2{\mathrm{CH}}_3$

D.  but-3-en-1-ol, ${\mathrm{CH}}_2={\mathrm{CHCH}}_2{\mathrm{CH}}_2\mathrm{OH}$

Which compound with the molecular formula ${\mathrm{C}}_4{\mathrm{H}}_8\mathrm{O}$ has this high resolution ${}_1\mathrm{H} \mathrm{NMR}$?

From: libretexts.org. Courtesy of Chris Schaller, Professor (Chemistry)
at College of Saint Benedict/Saint John’s University.

A.  but-3-en-2-ol, ${\mathrm{CH}}_2=\mathrm{CHCH}\left(\mathrm{OH}\right){\mathrm{CH}}_3$

B.  butanal, ${\mathrm{CH}}_3{\mathrm{CH}}_2{\mathrm{CH}}_2\mathrm{CHO}$

C.  butanone, ${\mathrm{CH}}_3{\mathrm{COCH}}_2{\mathrm{CH}}_3$

D.  but-3-en-1-ol, ${\mathrm{CH}}_2={\mathrm{CHCH}}_2{\mathrm{CH}}_2\mathrm{OH}$

Which compound with the molecular formula ${\mathrm{C}}_4{\mathrm{H}}_8\mathrm{O}$ has this high resolution ${}_1\mathrm{H} \mathrm{NMR}$?

From: libretexts.org. Courtesy of Chris Schaller, Professor (Chemistry)
at College of Saint Benedict/Saint John’s University.

A.  but-3-en-2-ol, ${\mathrm{CH}}_2=\mathrm{CHCH}\left(\mathrm{OH}\right){\mathrm{CH}}_3$

B.  butanal, ${\mathrm{CH}}_3{\mathrm{CH}}_2{\mathrm{CH}}_2\mathrm{CHO}$

C.  butanone, ${\mathrm{CH}}_3{\mathrm{COCH}}_2{\mathrm{CH}}_3$

D.  but-3-en-1-ol, ${\mathrm{CH}}_2={\mathrm{CHCH}}_2{\mathrm{CH}}_2\mathrm{OH}$

Which compound produces the following ¹H NMR spectrum?

SDBS, National Institute of Advanced Industrial Science and Technology (AIST).

A.  Propane

B.  Propanone

C.  Propanal

D.  2,2-dimethylpropane

Which compound produces the following ¹H NMR spectrum?

SDBS, National Institute of Advanced Industrial Science and Technology (AIST).

A.  Propane

B.  Propanone

C.  Propanal

D.  2,2-dimethylpropane

Which compound produces the following ¹H NMR spectrum?

SDBS, National Institute of Advanced Industrial Science and Technology (AIST).

A.  Propane

B.  Propanone

C.  Propanal

D.  2,2-dimethylpropane

Which compound produces the following ¹H NMR spectrum?

SDBS, National Institute of Advanced Industrial Science and Technology (AIST).

A.  Propane

B.  Propanone

C.  Propanal

D.  2,2-dimethylpropane

What information can be deduced from the splitting pattern of ¹H NMR signals?

A.  total number of hydrogen atoms in a compound

B.  number of hydrogen atoms on adjacent atom(s)

C.  functional group on which hydrogen atoms are located

D.  number of hydrogen atoms in a particular chemical environment

What information can be deduced from the splitting pattern of ¹H NMR signals?

A.  total number of hydrogen atoms in a compound

B.  number of hydrogen atoms on adjacent atom(s)

C.  functional group on which hydrogen atoms are located

D.  number of hydrogen atoms in a particular chemical environment

What information can be deduced from the splitting pattern of ¹H NMR signals?

A.  total number of hydrogen atoms in a compound

B.  number of hydrogen atoms on adjacent atom(s)

C.  functional group on which hydrogen atoms are located

D.  number of hydrogen atoms in a particular chemical environment

What information can be deduced from the splitting pattern of ¹H NMR signals?

A.  total number of hydrogen atoms in a compound

B.  number of hydrogen atoms on adjacent atom(s)

C.  functional group on which hydrogen atoms are located

D.  number of hydrogen atoms in a particular chemical environment

Which spectra would show the difference between propan-2-ol, CH₃CH(OH)CH₃, and propanal, CH₃CH₂CHO?

I.   mass
II.  infrared
III. ¹H NMR

A.  I and II only

B.  I and III only

C.  II and III only

D.  I, II and III

Which spectra would show the difference between propan-2-ol, CH₃CH(OH)CH₃, and propanal, CH₃CH₂CHO?

I.   mass
II.  infrared
III. ¹H NMR

A.  I and II only

B.  I and III only

C.  II and III only

D.  I, II and III

Which compound produces the following ¹H NMR spectrum?

^{[Spectral Database for Organic Compounds, SDBS. SDBS Compounds and Spectral Search. [graph] Available at:
https://sdbs.db.aist.go.jp [Accessed 3 January 2019].]}

A.  propanal

B.  propanone

C.  propane

D.  methlypropane

Which compound produces the following ¹H NMR spectrum?

^{[Spectral Database for Organic Compounds, SDBS. SDBS Compounds and Spectral Search. [graph] Available at:
https://sdbs.db.aist.go.jp [Accessed 3 January 2019].]}

A.  propanal

B.  propanone

C.  propane

D.  methlypropane

Which compound produces the following ¹H NMR spectrum?

^{[Spectral Database for Organic Compounds, SDBS. SDBS Compounds and Spectral Search. [graph] Available at:
https://sdbs.db.aist.go.jp [Accessed 3 January 2019].]}

A.  propanal

B.  propanone

C.  propane

D.  methlypropane

Which compound produces the following ¹H NMR spectrum?

^{[Spectral Database for Organic Compounds, SDBS. SDBS Compounds and Spectral Search. [graph] Available at:
https://sdbs.db.aist.go.jp [Accessed 3 January 2019].]}

A.  propanal

B.  propanone

C.  propane

D.  methlypropane

Given equimolar concentrations, which substance would produce the strongest signal in a ¹H NMR spectrum?

A.  (CH₃)₃CH

B.  C₆H₆

C.  C₈H₁₈

D.  Si(CH₃)₄

Given equimolar concentrations, which substance would produce the strongest signal in a ¹H NMR spectrum?

A.  (CH₃)₃CH

B.  C₆H₆

C.  C₈H₁₈

D.  Si(CH₃)₄

Given equimolar concentrations, which substance would produce the strongest signal in a ¹H NMR spectrum?

A.  (CH₃)₃CH

B.  C₆H₆

C.  C₈H₁₈

D.  Si(CH₃)₄

Given equimolar concentrations, which substance would produce the strongest signal in a ¹H NMR spectrum?

A.  (CH₃)₃CH

B.  C₆H₆

C.  C₈H₁₈

D.  Si(CH₃)₄

Deduce the number of signals that you would expect in the ¹H NMR spectrum of nitrobenzene and the relative areas of these.

Deduce the number of signals that you would expect in the ¹H NMR spectrum of nitrobenzene and the relative areas of these.

Deduce the number of signals that you would expect in the ¹H NMR spectrum of nitrobenzene and the relative areas of these.

Deduce the number of signals that you would expect in the ¹H NMR spectrum of nitrobenzene and the relative areas of these.

Deduce the number of signals that you would expect in the ¹H NMR spectrum of nitrobenzene and the relative areas of these.

Deduce the number of signals that you would expect in the ¹H NMR spectrum of nitrobenzene and the relative areas of these.

Suggest two differences in the ¹H NMR of but-2-ene and the organic product from (d)(ii).

Suggest two differences in the ¹H NMR of but-2-ene and the organic product from (d)(ii).

Suggest two differences in the ¹H NMR of but-2-ene and the organic product from (d)(ii).

Suggest two differences in the ¹H NMR of but-2-ene and the organic product from (d)(ii).

Suggest two differences in the ¹H NMR of but-2-ene and the organic product from (d)(ii).

Suggest two differences in the ¹H NMR of but-2-ene and the organic product from (d)(ii).

Which organic compound has the ¹H NMR shown?

^{Source: Spectral Database for Organic Compounds, SDBS, n.d. [online] Available at:
https://sdbs.db.aist.go.jp/sdbs/cgi-bin/direct_frame_top.cgi [Accessed 6 October 2021].}

A.  Methanal

B.  Ethanoic acid

C.  Methyl ethanoate

D.  Propanoic acid

Which organic compound has the ¹H NMR shown?

^{Source: Spectral Database for Organic Compounds, SDBS, n.d. [online] Available at:
https://sdbs.db.aist.go.jp/sdbs/cgi-bin/direct_frame_top.cgi [Accessed 6 October 2021].}

A.  Methanal

B.  Ethanoic acid

C.  Methyl ethanoate

D.  Propanoic acid