CHM 2120 – Problem set 3

In this assignment:
- NMR spectroscopy
- IR spectroscopy
- Problem-solving and structure identification

1. Associate each of the following IR spectra with one of the following compounds and
justify your answer.
a. Propanoic acid
b. 2-Pentanol
c. Benzyl alcohol
d. Acetophenone
 Problem set 3 – NMR, IR

1. cont.

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 Problem set 3 – NMR, IR

2. Associate each of the following IR spectra with one of the following compounds and
justify your answer.
a. 2-Propyn-1-ol
b. 1-Pentyne
c. 4-Methylpentanenitrile
d. p-Acetylbenzonitrile

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 Problem set 3 – NMR, IR

2. Cont.

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 Problem set 3 – NMR, IR

3. Give the number of peaks expected in the 1H NMR for the indicated protons in each
of the following structures:

a) b) c)
O H O
H3C C O
CH3 H2
H3C C Cl CH3
H2
H

d) e) f)
H3C H2 H2N CO2H
C H
CH3 H3C O H CH3

H O

4. How many signals would be expected in the 1H NMR of the following molecules?

a) b) O c)
O H O

Cl CH3
H

d) e) f)
H3C H2 O
O
C H
CH3 H3C O

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 Problem set 3 – NMR, IR

5. Explain the following differences in chemical shift.

Me δ = 6.7 ppm
a) Me b)
O H O
H H

H
δ = 7.1 δ = 7.7 ppm
δ = 6.1 ppm

c) δ = 4.41 ppm d) Me
O H2
C O N H δ = 5.6 ppm
O C CH3
H2
H δ = 4.2 ppm
δ = 3.6 ppm

6. Determine the structure of the following unknowns using the table to fill in your
answers.
a.

Signal δ Integration Multiplicity Comments

A

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 Problem set 3 – NMR, IR

b.

Signal δ Integration Multiplicity Comments

A

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 Problem set 3 – NMR, IR

c.

Signal δ Integration Multiplicity Comments

A

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 Problem set 3 – NMR, IR

7. Determine the most likely structure of a compound, with the molecular formula
C9H12, which gave a 1H NMR spectrum consisting of:
a doublet at δ 1.25
a septet at δ 2.90 and
a multiplet at δ 7.25

I II III IV V ]

8. A compound with the molecular formula C10H13Cl gave the following 1H NMR
spectrum:
singlet, δ 1.6
singlet, δ 3.1
multiplet, δ 7.2 (5H)

The most likely structure for the compound is:

Cl Cl
Cl
I II III
Cl
Cl

IV V

9. Determine the likely structure for a compound A (C6H10O), which is found to

decolorize bromine in carbon tetrachloride. Its spectral data is as follows:
1
H NMR IR
-1
triplet, δ 1.0 singlet, δ 2.4 2200 cm (sharp)
singlet, δ 1.4 singlet, δ 3.4 3300 cm-1 (sharp)
quartet, δ 1.6 3500 cm-1 (broad)

OH
OH OH

I II III

OH
OH
IV V

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 Problem set 3 – NMR, IR

10. Briefly explain how you might distinguish between the following substances by
comparing their 1H-NMR spectra:
O
O
O
O
I II

11. An unknown compound has the formula C6H12O. Elucidate the structure of the
molecule by scrutinizing its IR and 1H NMR spectra, shown below.

Signal δ Integration Multiplicity Comments

A

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 Problem set 3 – NMR, IR

12. An unknown compound, I, has the formula C3H7NO2. Elucidate the structure of I
by scrutinizing its IR and 1H NMR spectra, shown below.

Signal δ Integration Multiplicity Comments

A

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 Problem set 3 – NMR, IR

1.

2.

3.

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37.

Chemical Formula: C 5 H8 O
Note: long-range coupling is
2H observed in this example

3H
triplet
2H
multiplet

1H

4 3 2 1 0
PPM

38.

Chemical Formula: C5 H8 O
2H
triplet
Note: another compound
that exhibits long-range coupling
3H

2H
multiplet
1H

5 4 3 2 1 0
PPM

39.

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 Problem set 3 – NMR, IR

40.

Chemical Formula: C 5 H8 O
2H 2H
Note: This compound
exhibits long-range
1H coupling
triplet 2H (multiplet)

1H

4 3 2 1 0
PPM

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42.

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46.
2H

2H Chemical Formula: C 7H 5 BrO

1H

9 8 7 6 5 4 3 2 1 0
PPM

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48.

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