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Set 1

Q1. The molecule shown below has how many proton environments:

(a) 1
(b) 2
(c) 3
(d) 4
(e) 5

Q2. The molecule shown below has how many proton environments:

(a) 1
(b) 2
(c) 3
(d) 4
(e) 5

Q3. The expected multiplicity of the 1H environment indicated is

(a) singlet
(b) doublet
(c) triplet
(d) quartet
(e) quintet

Q4. The molecule shown below has how many carbon environments:

(a) 3
(b) 4
(c) 5
(d) 6
(e) 7
Q5. The molecule shown below has how many carbon environments:

(a) 1
(b) 2
(c) 3
(d) 4
(e) 5

Q6. Given the molecular formula of C8H7Br, and the spectrum below, use the integrals to
determine the number of protons present in each signal (write the values at the points
indicated).

Q7. In the spectrum below, which peak is the base peak?


Q8. In the spectrum below, which peak is the parent ion?

Q9. Use the mass spectrum and the elemental analysis data provided below to calculate
the molecular formula for the unknown compound.

Elemental Data
C 72.4%
H 4.5%
N 7.0%
O 16.1%

Q10. Calculate the index of hydrogen deficiency (degree of unsaturation) for the molecular
formula C6H9NO2
Q11. Propose a structure for compound with the formula C8H8O2 that has an absorption
peak at 1720 cm-1 in its IR spectrum (note, more than one structure is possible).

Q12. In the structure shown below, write a characteristic IR absorption band that would
help you to identify the compound.

Q13. Which of the following compounds would you expect to exhibit an absorption at 2250
cm-1

Q14. A 1H-decoupled 13C spectrum shows


(a) all 13C envi ronments as singlets
(b) all 13C environments as singlets, but not quaternary carbons
(c) CH and CH3 positive, and CH2 negative, but quaternary carbons are absent
(d) only CH environments
(e) all 13C environments as singlets/multiplets depending upon the number of attached
1
Hs
Set 2
Q1. The molecule shown below has how many proton environments:

(a) 3
(b) 4
(c) 5
(d) 6
(e) 7

Q2. The molecule shown below has how many proton environments:

(a) 1
(b) 2
(c) 3
(d) 4
(e) 5

Q3. The expected multiplicity of the 1H environment indicated is

(a) singlet
(b) doublet
(c) triplet
(d) quartet
(e) quintet

Q4. The molecule shown below has how many carbon environments:

(a) 2
(b) 3
(c) 4
(d) 5
(e) 6
Q5. The molecule shown below has how many carbon environments:

(a) 2
(b) 3
(c) 4
(d) 5
(e) 6

Q6. Given the molecular formula of C12H14O4, and the spectrum below, use the integrals
to determine the number of protons present in each signal (write the values at the points
indicated).

Q7. In the spectrum below, which peak is the base peak?


Q8. In the spectrum below, which peak is the parent ion?

Q9. Use the mass spectrum and the elemental analysis data provided below to calculate
the molecular formula for the unknown compound.

Elemental Data
C 72.3%
H 8.4%
O 19.3%

Q10. Calculate the index of hydrogen deficiency (degree of unsaturation) for the molecular
formula C7H12O2
Q11. Propose a structure for compound with the formula C8H12O that has an absorption
peak at 1710 cm-1 in its IR spectrum (note, more than one structure is possible).

Q12. In the structure shown below, write a characteristic IR absorption band that would
help you to identify the compound.

Q13. Which of the following compounds would you expect to exhibit an absorption at
3520 cm-1

Q14. A 1H-coupled 13C spectrum shows


(a) all 13C environments as singlets
(b) all 13C environments as singlets, but not quaternary carbons
(c) CH and CH3 positive, and CH2 negative, but quaternary carbons are absent
(d) only CH environments
(e) all 13C environments as singlets/multiplets depending upon the number of attached
1
Hs
Set 3
Q1. The molecule shown below has how many proton environments:

(a) 1
(b) 2
(c) 3
(d) 4
(e) 5

Q2. The molecule shown below has how many proton environments:

(a) 1
(b) 2
(c) 3
(d) 4
(e) 5

Q3. The expected multiplicity of the 1H environment indicated is

(a) singlet
(b) doublet
(c) triplet
(d) quartet
(e) quintet

Q4. The molecule shown below has how many carbon environments:

(a) 1
(b) 2
(c) 3
(d) 4
(e) 5
Q5. The molecule shown below has how many carbon environments:

(a) 1
(b) 2
(c) 3
(d) 4
(e) 5

Q6. Given the molecular formula of C8H6BrNO2, and the spectrum below, use the
integrals to determine the number of protons present in each signal (write the values at the
points indicated).

Q7. In the spectrum below, which peak is the base peak?


Q8. In the spectrum below, which peak is the parent ion?

Q9. Use the mass spectrum and the elemental analysis data provided below to calculate
the molecular formula for the unknown compound.

Elemental Data
C 79.2%
H 5.7%
O 15.1%

Q10. Calculate the index of hydrogen deficiency (degree of unsaturation) for the molecular
formula C8H10
Q11. Propose a structure for compound with the formula C7H12O2 that has an absorption
peak at 1720 cm-1 in its IR spectrum (note, more than one structure is possible).

Q12. In the structure shown below, write a characteristic IR absorption band that would
help you to identify the compound.

Q13. Which of the following compounds would you expect to exhibit an absorption at 1540
cm-1

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