Deck 9: Nuclear Magnetic Resonance and Mass Spectrometry

Question 1

Which one of the following best represents the predicted approximate chemical shift and coupling for the hydrogen(s)indicated with the arrow in the compound nicotine?

A)1.00 ppm,singlet
B)2.00 ppm,doublet
C)3.00 ppm,broad multiplet
D)5.00 ppm,broad multiplet
E)None of these choices.

Answer 1

None of these choices.

Question 2

Which one of the following best represents the predicted approximate chemical shift and coupling for the hydrogen(s)indicated with the arrow?

A)3.00 ppm,doublet
B)3.00 ppm,triplet
C)5.00 ppm,triplet
D)1.00 ppm,doublet
E)3.00 ppm,singlet

Answer 2

3.00 ppm,singlet

Question 3

Which one of the following best represents the predicted approximate chemical shift and coupling for the hydrogen(s)indicated with the arrow in the compound nicotine?

A)1.00 ppm,triplet
B)2.00 ppm,doublet
C)5.00 ppm,triplet
D)7.00 ppm.mulitplet
E)None of these choices.

Answer 3

5.00 ppm,triplet

Question 4

For the following compound how many different signals would you see in the proton NMR? (Assume that you can see them all.)

A)4
B)5
C)6
D)7
E)8

Question 5

For the compound adamantine,how many different signals would you see in the proton NMR? (Assume that you can see them all.)

A)1
B)2
C)3
D)4
E)None of these choices.

Question 6

A downfield ( $\delta$ 9-10)singlet is observed in the ¹H NMR spectrum of:

A)
B)
C)
D)
E)

Question 7

For the following compound how many different signals would you see in the proton NMR? (Assume that you can see them all.)

A)1
B)2
C)3
D)4
E)5

Question 8

For the following compound how many different signals would you see in the proton NMR? (Assume that you can see them all.)

A)1
B)2
C)3
D)4
E)5

Question 9

Which one of the following best represents the predicted approximate chemical shift and coupling for the hydrogen(s)indicated with the arrow?

A)1.10 ppm,singlet
B)2.10 ppm,doublet
C)3.40 ppm,singlet
D)4.5 ppm,singlet
E)3.5 ppm,quartet

Question 10

Predict the splitting pattern you would observe for the proton at C1 of 2,3-dimethyl-2-phenylbutane.

A)Doublet
B)Singlet
C)Quartet
D)Septet
E)Octet

Question 11

For the following compound how many different signals would you see in the proton NMR? (Assume that you can see them all.)

A)4
B)5
C)6
D)7
E)8

Question 12

For the compound dimedone,how many different signals would you see in the proton NMR? (Assume that you can see them all.)

A)2
B)3
C)4
D)5
E)None of these choices.

Question 13

Which one of the following best represents the predicted approximate chemical shift and coupling for the hydrogen(s)indicated with the arrow?

A)3.00 ppm,doublet
B)3.00 ppm,triplet
C)5.00 ppm,triplet
D)1.00 ppm,doublet
E)5.40 ppm,multiplet

Question 14

Which one of the following best represents the predicted approximate chemical shift and coupling for the hydrogen(s)indicated with the arrow?

A)5.40 ppm,multiplet
B)2.00 ppm,multiplet
C)2.00 ppm,doublet
D)2.00 ppm,quartet
E)5.40 ppm,doublet

Question 15

Which one of the following best represents the predicted approximate chemical shift and coupling for the hydrogen(s)indicated with the arrow?

A)5.40 ppm,doublet
B)1.00 ppm,multiplet
C)2.00 ppm,doublet
D)1.00 ppm,doublet
E)5.40 ppm,multiplet

Question 16

How many signals would you expect to find in the ¹H NMR spectrum of CH₃OCH₂CH₂OCH₃?

A)1
B)2
C)3
D)4
E)5

Question 17

Which one of the following best represents the predicted approximate chemical shift and coupling for the hydrogen(s)indicated with the arrow?

A)1.00 ppm,singlet
B)2.10 ppm,singlet
C)2.10 ppm,quartet
D)3.00 ppm,singlet
E)2.10 ppm,triplet

Question 18

Which one of the following best represents the predicted approximate chemical shift and coupling for the hydrogen(s)indicated with the arrow?

A)1.00 ppm,quartet
B)2.40 ppm,singlet
C)2.40 ppm,quartet
D)3.00 ppm,quartet
E)1.00 ppm,triplet

Question 19

Which one of the following best represents the predicted approximate chemical shift and coupling for the hydrogen(s)indicated with the arrow?

A)1.00 ppm,quartet
B)2.40 ppm,singlet
C)2.40 ppm,quartet
D)3.00 ppm,quartet
E)2.40 ppm,triplet

Question 20

Which one of the following best represents the predicted approximate chemical shift and coupling for the hydrogen(s)indicated with the arrow in the compound nicotine?

A)6.00 ppm,singlet
B)5.00 ppm.doublet
C)7.00 ppm,multiplet
D)9.00 ppm,triplet
E)none of these choices

Question 21

How many chemically distinct ¹H NMR signals are there in the following compound?

A)1
B)2
C)3
D)4
E)5

Question 22

For the following compound how many different signals would you see in the proton NMR? (Assume that you can see them all.)

A)4
B)5
C)6
D)7
E)8

Question 23

A compound C₅H₁₁Cl which exhibits only two singlets in the ¹H NMR spectrum must be:

A)1-Chloropentane
B)1-Chloro-2,2-dimethylpropane
C)1-Chloro-2-methylbutane
D)3-Chloropentane
E)1-Chloro-3-methylbutane

Question 24

Which proton(s)of the compound below would appear as a triplet in the ¹H NMR spectrum?

A)The protons on carbon II.
B)The protons on carbon I and V.
C)The protons on carbon III and V.
D)The protons on carbon III and IV.
E)The protons on carbon V.

Question 25

Which proton(s)of the compound below would appear as a doublet in the ¹H NMR spectrum?

A)The protons on carbon I.
B)The protons on carbon II.
C)The protons on carbon III.
D)The protons on carbon IV.
E)The protons on carbon V.

Question 26

Consider the expected ¹H NMR spectrum of 2,4-dimethyl-1,4-pentadiene.Which of the following is likely to be observed?

A)7 signals: all singlets
B)4 signals: all singlets
C)3 signals: all singlets
D)3 signals: one singlet,2 doublets
E)4 signals: two singlets,two doublets

Question 27

Which one of the following best represents the predicted approximate chemical shift and coupling for the hydrogen(s)indicated with the arrow?

A)1.00 ppm,doublet
B)2.00 ppm,singlet
C)2.00 ppm,triplet
D)2.00 ppm,doublet
E)1.00 ppm,triplet

Question 28

How many ¹H NMR signals would you expect from this compound?

A)1
B)2
C)3
D)4
E)5

Question 29

Consider the expected ¹H NMR spectrum of 1,1,3,3-tetramethylcyclopentane.Which of the following is likely to be observed?

A)7 signals: all singlets
B)7 signals: 4 singlets,3 doublets
C)3 signals: all singlets
D)3 signals: one singlet,2 doublets
E)3 signals: two singlets,one doublet

Question 30

How many ¹H NMR signals would trans-1,2-dichlorocyclopropane give?

A)1
B)2
C)3
D)4
E)5

Question 31

Which proton(s)of the compound below would appear as a septet in the ¹H NMR spectrum?

A)The protons on carbon I
B)The protons on carbon II
C)The protons on carbon III
D)The protons on carbon IV
E)The protons on carbon V

Question 32

If all the protons of 1-fluoropentane could be discerned,which would you expect to be at the lowest field in the ¹H NMR spectrum of this compound?

A)Protons on carbon I
B)Protons on carbon II
C)Protons on carbon III
D)Protons on carbon IV
E)Protons on carbon V

Question 33

The ¹H NMR spectrum of which of these compounds would consist of a triplet,singlet and quartet only?

A)2-chloro-4-methylpentane
B)3-chloro-2-methylpentane
C)3-chloropentane
D)1-chloro-2,2-dimethylbutane
E)3-chloro-3-methylpentane

Question 34

A compound that would show two triplets and a septet in the ¹H NMR spectrum could be:

A)3-ethylpentane
B)2-bromopropane
C)chlorocyclopropane
D)1-iodopropane
E)none of these choices

Question 35

Predict the splitting pattern you would observe for the proton at C4 of 2,3-dimethyl-2-phenylbutane.

A)Doublet
B)Singlet
C)Quartet
D)Septet
E)Octet

Question 36

The ¹H NMR signal for which of the indicated protons will occur at the lowest frequency (most upfield signal)?

A)I
B)II
C)III
D)IV
E)V

Question 37

Which of the following compounds would not be represented by a lone singlet in the proton NMR?

A)cyclohexane
B)benzene
C)dimethyl ether (CH₃-O-CH₃)
D)1,2-ethanediol
E)none of these choices

Question 38

How many ¹H NMR signals would cis-1,2-dichlorocyclopropane give?

A)1
B)2
C)3
D)4
E)5

Question 39

Predict the splitting pattern you would observe for the proton at C3 of 2,3-dimethyl-2-phenylbutane.

A)Doublet
B)Singlet
C)Quartet
D)Septet
E)Octet

Question 40

Which one of the following best represents the predicted approximate chemical shift and coupling for the hydrogen(s)indicated with the arrow?

A)1.10 ppm,singlet
B)2.10 ppm,triplet
C)3.40 ppm,triplet
D)4.5 ppm,singlet
E)5.3 ppm,doublet

Question 41

A compound with the molecular formula C₈H₉ClO gave the following ¹H NMR spectrum: triplet, $\delta$ 3.7
Triplet, $\delta$ 4.2
Multiplet, $\delta$ 7.1
There was no evidence of an -OH band in the IR spectrum.The most likely structure for the compound is:

A)I
B)II
C)III
D)IV
E)V

Question 42

What is the structure of the compound in the following ¹H-NMR spectrum with the molecular formula C₈H₁₄? Relative integration is shown.

A)
B)
C)
D)
E)

Question 43

What is the structure of the compound in the following ¹H-NMR spectrum with the molecular formula C₆H₁₁N? In the IR spectrum you notice a stretch at about 2250 cm^-1.Relative integration is shown.

A)
B)
C)
D)
E)

Question 44

The ¹H NMR spectrum of which of the compounds below,all of formula C₇H₁₂O₂,would consist of two singlets only?

A)I
B)II
C)III
D)IV
E)V

Question 45

What is the structure of the compound in the following ¹H-NMR spectrum with the molecular formula C₉H₁₀O₂? Relative integration is shown.

A)
B)
C)
D)
E)

Question 46

Consider the expected splitting of the C2 proton signal in the ¹H NMR spectrum of 1,1-dibromopentane.Presuming that the coupling constants for neighboring protons are sufficiently different,and that the instrument has sufficient resolving power,what is the theoretical multiplicity of the C2 proton signal?

A)3
B)4
C)5
D)6
E)8

Question 47

What is the structure of the compound in the following ¹H-NMR spectrum with the molecular formula C₄H₈O? Relative integration is shown.

A)
B)
C)
D)
E)

Question 48

A compound with the molecular formula C₄H₁₀O gives a ¹H NMR spectrum consisting only of a quartet centered at $\delta$ 3.5 and a triplet at $\delta$ 1.1.The most likely structure for the compound is:

A)
B)
C)CH₃CH₂CH₂CH₂OH
D)CH₃CH₂OCH₂CH₃
E)

Question 49

A compound with the molecular formula C₆H₁₅N gave the following ¹H NMR spectrum: triplet, $\delta$ 0 0.90
Quartet, $\delta$ 2.4
There were no other signals.The most likely structure for the compound is:

A)
B)
C)CH₃CH₂CH₂CH₂CH₂CH₂NH₂
D)
E)

Question 50

Which of these compounds will not be represented by a singlet only in the ¹H NMR spectrum?

A)Neopentane
B)Hexamethylbenzene
C)Isobutane
D)(Z)-1,2-Dichloroethene
E)(E)-1,2-Dichloroethene

Question 51

A compound with the molecular formula C₈H₉BrO gave the following ¹H NMR spectrum: triplet, $\delta$ 1.4
Quartet, $\delta$ 3.9
Multiplet, $\delta$ 7.0 (4H)
There was no evidence of an -OH band in the IR spectrum.A possible structure for the compound is:

A)I
B)II
C)III
D)IV
E)V

Question 52

Determine the most likely structure of a compound,with the molecular formula C₉H₁₂,which gave a ¹H NMR spectrum consisting of: a doublet at $\delta$ 1.25
A septet at $\delta$ 2.90 and
A multiplet at $\delta$ 7.25 ]

A)I
B)II
C)III
D)IV
E)V

Question 53

A compound with the molecular formula C₃H₆Cl₂ gave a ¹H NMR spectrum consisting only of a triplet centered at $\delta$ 3.7 and a quintet centered at $\delta$ 2.2.The most likely structure for the compound is:

A)CH₃CH₂CHCl₂
B)CH₃CHClCH₂Cl
C)ClCH₂CHClCH₃
D)ClCH₂CH₂CH₂Cl
E)CH₃CCl₂CH₃

Question 54

What is the structure of the compound in the following ¹H-NMR spectrum with the molecular formula C₁₀H₁₂O₂? Relative integration is shown.

A)
B)
C)
D)
E)

Question 55

Consider the expected splitting of the C2 proton signal in the ¹H NMR spectrum of 2-ethyl-1,3-propanediol.Presuming that the coupling constants for neighboring protons are sufficiently different,and that the instrument has sufficient resolving power,what is the theoretical multiplicity of the C2 proton signal?

A)6
B)7
C)8
D)12
E)15

Question 56

What is the theoretical multiplicity of the C-2 proton signal in the ¹H NMR spectrum of 2-hydroxymethyl-1,3-propanediol,shown below?

A)1
B)6
C)7
D)8
E)9

Question 57

The ¹H NMR spectrum of which of the compounds below,all of formula C₇H₁₂O₂,would consist of a singlet,a doublet and a triplet only?

A)I
B)II
C)III
D)IV
E)V

Question 58

A compound with the molecular formula C₁₀H₁₃Cl gave the following ¹H NMR spectrum: singlet, $\delta$ 1.6
Singlet, $\delta$ 3.1
Multiplet, $\delta$ 7.2 (5H)
The most likely structure for the compound is:

A)I
B)II
C)III
D)IV
E)V

Question 59

What is the structure of the compound in the following ¹H-NMR spectrum with the molecular formula C₁₀H₂₀? Relative integration is shown.

A)
B)
C)
D)
E)

Question 60

The ¹H NMR spectrum of which of the compounds below,all of formula C₇H₁₂O₂,would consist of three singlets only?

A)I
B)II
C)III
D)IV
E)V

Question 61

What is the structure of the compound in the following ¹H-NMR spectrum with the molecular formula C₅H₁₀O? The IR spectrum does not show any characteristic stretches around 1700 cm^-1.Relative integration is shown.

A)
B)
C)
D)
E)

Question 62

In the structure shown,H_a and H_b are classified as:

A)homotopic protons.
B)vicinal protons.
C)enantiotopic protons.
D)diastereotopic protons.
E)isomeric protons.

Question 63

What is the structure of the compound in the following ¹H-NMR spectrum with the molecular formula C₈H₁₆O? Relative integration is shown.

A)
B)
C)
D)
E)

Question 64

In the structure shown,H_b and H_c are classified as:

A)homotopic protons.
B)geminal protons.
C)enantiotopic protons.
D)diastereotopic protons.
E)isomeric protons.

Question 65

Determine the likely structure for a compound A (C₆H₁₀O),which is found to decolorize bromine in carbon tetrachloride.Its spectral data is as follows: ¹H NMR IR
Triplet, $\delta$ 1.0 singlet, $\delta$ 2.4 2200 cm^-1 (sharp)
Singlet, $\delta$ 1.4 singlet, $\delta$ 3.4 3300 cm^-1 (sharp)
Quartet, $\delta$ 1.6 3500 cm^-1 (broad)

A)I
B)II
C)III
D)IV
E)V

Question 66

What is the structure of the compound in the following ¹H-NMR spectrum with the molecular formula C₆H₁₂O which shows no characteristic stretches in the IR between 3600-3300 cm^-1,but does around 1600 cm^-1? Relative integration is shown.

A)
B)
C)
D)
E)

Question 67

For the C2 methylene group in 1-bromopropane, the theoretical multiplicity in the ¹H NMR spectrum,presuming that J_ab is sufficiently different from J_bc and that the instrument has sufficient resolving power,is which of these?

A)2
B)5
C)6
D)8
E)12

Question 68

What is the structure of the compound in the following ¹H-NMR spectrum with the molecular formula C₆H₁₂O₂? Relative integration is shown.

A)
B)
C)
D)
E)

Question 69

A compound with the molecular formula C₁₀H₁₄ gave the following ¹H NMR spectrum: doublet, $\delta$ 1.2
Singlet, $\delta$ 2.3
Septet, $\delta$ 2.8
Multiplet, $\delta$ 7.1
A possible structure for the compound is:

A)I
B)II
C)III
D)IV
E)V

Question 70

In NMR terminology,protons H_a and H_b are said to be:

A)Identical
B)Enantiotopic
C)Diastereotopic
D)Homotopic
E)Mesotopic

Question 71

A compound C₅H₁₀O gave the following spectral data: ¹H NMR spectrum IR spectrum
Doublet, $\delta$ 1.10 strong peak
Singlet, $\delta$ 2.10 near 1720 cm^-1
Septet, $\delta$ 2.50
Which is a reasonable structure for the compound?

A)I
B)II
C)III
D)IV
E)V

Question 72

What is the structure of the compound in the following ¹H-NMR spectrum with the molecular formula C₆H₁₂? Relative integration is shown.

A)
B)
C)
D)
E)

Question 73

What is the structure of the compound in the following ¹H-NMR spectrum with the molecular formula C₆H₁₀O₂? Relative integration is shown.

A)
B)
C)
D)
E)

Question 74

In the structure shown,H_a and H_b are classified as:

A)homotopic protons.
B)vicinal protons.
C)enantiotopic protons.
D)diastereotopic protons.
E)isomeric protons.

Question 75

What is the structure of the compound in the following ¹H-NMR spectrum with the molecular formula C₉H₁₂O? Relative integration is shown.

A)
B)
C)
D)
E)

Question 76

A compound C₄H₉Br gave the following ¹H NMR spectrum: triplet, $\delta$ 1.0 (3H); doublet, $\delta$ 1.7; multiplet $\delta$ 1.8; multiplet, $\delta$ 4.1 (1H)
Which is a reasonable structure for the compound?

A)CH₃CH₂CHBrCH₃
B)CH₃CH₂CH₂CH₂Br
C)(CH₃)₂CHCH₂Br
D)(CH₃)₃CBr

Question 77

What is the structure of the compound in the following ¹H-NMR spectrum with the molecular formula C₅H₈O? The IR spectrum does show a characteristic stretch around 1700 cm^-1.Relative integration is shown.

A)
B)
C)
D)
E)

Question 78

What is the structure of the compound in the following ¹H-NMR spectrum with the molecular formula C₄H₇Br? Relative integration is shown.

A)
B)
C)
D)
E)

Question 79

In the structure shown,H_a and H_b are classified as:

A)homotopic protons.
B)vicinal protons.
C)enantiotopic protons.
D)diastereotopic protons.
E)isomeric protons.

Question 80

Consider the expected splitting of signal "b" in the ¹H NMR spectrum of 1-methoxy-2-methylpropane,shown below.Presuming that J_ab is sufficiently different from J_bc and that the instrument has sufficient resolving power,what is the theoretical multiplicity of signal "b"?

A)8
B)9
C)12
D)21
E)24