Back to Product

Chapter 15 Nuclear Magnetic Resonance Spectroscopy Exam Prep

Organic Chemistry, 4e (Klein)

Chapter 15 Nuclear Magnetic Resonance Spectroscopy

1) NMR is an abbreviation for ________.

A) nuclide magnetic resonance

B) nuclear magnetic resonance

C) nuclear magnetic repetition

D) nuclide manipulation resonance

E) nuclear manipulation repetition

Diff: 1

Learning Objective: 15.1 Describe the interaction between electromagnetic radiation and atomic nuclei in a magnetic field that makes NMR spectroscopy possible

2) List the most common nuclei that are used in NMR.

A) 1H and 14C

B) 1H and 13C

C) 2H and 14C

D) 3H and 13C

E) 3H and 14C

Diff: 1

Learning Objective: 15.1 Describe the interaction between electromagnetic radiation and atomic nuclei in a magnetic field that makes NMR spectroscopy possible

3) Identify the nuclei that cannot be analyzed by NMR.

A) 15N

B) 14C

C) 19F

D) 31P

E) 1H

Diff: 1

Learning Objective: 15.1 Describe the interaction between electromagnetic radiation and atomic nuclei in a magnetic field that makes NMR spectroscopy possible

4) Which of the nuclei given cannot be analyzed by an NMR spectrometer?

A) nucleus with odd number of protons & odd number of neutrons

B) nucleus with odd number of protons &even number of neutrons

C) nucleus with even number of protons & odd number of neutrons

D) nucleus with even number of protons & even number of neutrons

E) none of these

Diff: 1

Learning Objective: 15.1 Describe the interaction between electromagnetic radiation and atomic nuclei in a magnetic field that makes NMR spectroscopy possible

5) How many nuclear spin states are possible for the 1H nucleus?

A) 1

B) 2

C) 4

D) 5

E) none of these

Diff: 1

Learning Objective: 15.1 Describe the interaction between electromagnetic radiation and atomic nuclei in a magnetic field that makes NMR spectroscopy possible

6) Which of the types of electromagnetic radiation shown is used in NMR spectroscopy?

A) UV

B) IR

C) visible

D) γ-rays

E) radio wave

Diff: 1

Learning Objective: 15.1 Describe the interaction between electromagnetic radiation and atomic nuclei in a magnetic field that makes NMR spectroscopy possible

7) ________ protons experience a net magnetic field strength that is smaller than the applied magnetic field.

A) Deshielded

B) Shielded

C) Paramagnetic

D) Diamagnetic

E) none of these

Diff: 2

Learning Objective: 15.1 Describe the interaction between electromagnetic radiation and atomic nuclei in a magnetic field that makes NMR spectroscopy possible

8) ________ protons experience a net magnetic field strength that is higher than that experienced by ________ protons.

A) Deshielded, shielded

B) Shielded, deshielded

C) Paramagnetic, diamagnetic

D) Shielded, diamagnetic

E) none of these

Diff: 2

Learning Objective: 15.1 Describe the interaction between electromagnetic radiation and atomic nuclei in a magnetic field that makes NMR spectroscopy possible

9) Which of the statements given is true about the relationship between the energy gap (∆E) between the spin states for a 1H nucleus and the strength of the external magnetic field?

A) they are inversely proportional

B) they are directly proportional

C) there is no relationship

D) the magnetic field is slightly less

E) none of these

Diff: 2

Learning Objective: 15.2 Describe how NMR spectrometers work and the process of preparing a sample for NMR spectral analysis

10) The strength of the magnetic field is a determining factor for the range of ________ that must be used for NMR spectrometer.

A) temperature

B) frequencies

C) tesla

D) none of these

Diff: 2

Learning Objective: 15.2 Describe how NMR spectrometers work and the process of preparing a sample for NMR spectral analysis

11) Which of the solvents given is not commonly used for acquiring a 1H NMR spectrum?

A) CDCl3

B) CCl4

C) CD3CN

D) CH3OH

E) D2O

Diff: 1

Learning Objective: 15.2 Describe how NMR spectrometers work and the process of preparing a sample for NMR spectral analysis

12) Which of the statements given is true about the number of signals in a 1H NMR spectrum?

A) it indicates the number of neighboring protons

B) it indicates the electronic environment of neighboring protons

C) it indicates the number of different kinds of protons

D) it indicates the electronic environment of absorbing protons

E) it indicates the number of protons in the signal

Diff: 1

Learning Objective: 15.3 State the significance of the number of signals, along with their locations, areas, and shapes, in am NMR spectrum

13) Which of the statements given is true about the location of signals in a 1H NMR spectrum?

A) it indicates the number of neighboring protons

B) it indicates the electronic environment of neighboring protons

C) it indicates the number of different protons

D) it indicates the electronic environment of absorbing protons

E) it indicates the number of protons in the signal

Diff: 1

Learning Objective: 15.3 State the significance of the number of signals, along with their locations, areas, and shapes, in am NMR spectrum

14) Which of the statements given is true about the area under each signal in a 1H NMR spectrum?

A) it indicates the number of neighboring protons

B) it indicates the electronic environment of neighboring protons

C) it indicates the number of different protons

D) it indicates the electronic environment of absorbing protons

E) it indicates the relative number of protons in the signal

Diff: 1

Learning Objective: 15.3 State the significance of the number of signals, along with their locations, areas, and shapes, in am NMR spectrum

15) Which of the statements given is true about the shape (multiplicity) of the signal in a 1H NMR spectrum?

A) it indicates the number of neighboring protons

B) it indicates the electronic environment of neighboring protons

C) it indicates the number of different protons

D) it indicates the electronic environment of absorbing protons

E) it indicates the number of protons in the signal

Diff: 1

Learning Objective: 15.3 State the significance of the number of signals, along with their locations, areas, and shapes, in am NMR spectrum

16) In an NMR spectrometer, the receiver coil records a complex signal, called a ________, which is converted into a spectrum via a mathematical technique called a ________.

A) free induction decay, NMR transformation

B) free induction decay, Fourier transformation

C) continuous wave induction, Fourier transformation

D) chemically equivalent induction, NMR transformation

E) chemically equivalent induction, Fourier transformation

Diff: 1

Learning Objective: 15.3 State the significance of the number of signals, along with their locations, areas, and shapes, in am NMR spectrum

17) Which of the type(s) of protons given are chemically non-equivalent?

A) homotopic

B) enantiotopic

C) diastereotopic

D) A & B

E) B & C

Diff: 2

Learning Objective: 15.4 Describe chemical equivalence and a procedure for determining whether two protons are homotopic, enantiotopic, or not chemically equivalent

18) Which of the type(s) of protons give are chemically equivalent?

A) homotopic

B) enantiotopic

C) diastereotopic

D) A & B

E) B & C

Diff: 1

Learning Objective: 15.4 Describe chemical equivalence and a procedure for determining whether two protons are homotopic, enantiotopic, or not chemically equivalent

19) Protons Ha and Hb in compound given are ________.

An illustration shows the structure of a compound. It has a seven carbon chain, in which C 4 is dash bonded to H a atom and wedge bonded to H b atom, respectively.

A) homotopic

B) enantiotopic

C) diastereotopic

D) mesotopic

E) none of these

Diff: 1

Learning Objective: 15.4 Describe chemical equivalence and a procedure for determining whether two protons are homotopic, enantiotopic, or not chemically equivalent

20) Protons Ha and Hb in the compound given are ________.

An illustration shows the structure of a compound. It has a cyclohexane ring, in which C 1 is bonded to a four carbon side chain. C 2 of the four carbon side chain is double bonded to C 3, and C 1 is dash bonded to H a atom and wedge bonded to H b atom, respectively.

A) homotopic

B) enantiotopic

C) diastereotopic

D) mesotopic

E) none of these

Diff: 2

Learning Objective: 15.4 Describe chemical equivalence and a procedure for determining whether two protons are homotopic, enantiotopic, or not chemically equivalent

21) Protons Ha and Hb in the compound given are ________.

An illustration shows the structure of a compound. It has a cyclohexane ring, in which C 1 is bonded to a three carbon side chain. C 1 of the three carbon side chain is double bonded to C 2, and C 1 is bonded to H a atom and H b atom, respectively.

A) homotopic

B) enantiotopic

C) diastereotopic

D) mesotopic

E) none of these

Diff: 2

Learning Objective: 15.4 Describe chemical equivalence and a procedure for determining whether two protons are homotopic, enantiotopic, or not chemically equivalent

22) Protons Ha and Hb in the compound given are ________.

An illustration shows the structure of a compound. It has a cyclohexane ring, in which C 1 is bonded to a three carbon chain. C 1 of the three carbon chain is dash bonded to a bromine atom and wedge bonded to a hydrogen atom. C 2 is dash bonded to H a atom and wedge bonded to H b atom.

A) homotopic

B) enantiotopic

C) diastereotopic

D) mesotopic

E) none of these

Diff: 2

Learning Objective: 15.4 Describe chemical equivalence and a procedure for determining whether two protons are homotopic, enantiotopic, or not chemically equivalent

23) Protons Ha and Hb in the compound given are ________.

An illustration shows the structure of a compound. It has a cyclobutane ring, in which C 1 is wedge bonded to a hydroxyl group, and C 2 is wedge bonded to H a atom and dash bonded to H b atom.

A) homotopic

B) enantiotopic

C) diastereotopic

D) mesotopic

E) none of these

Diff: 2

Learning Objective: 15.4 Describe chemical equivalence and a procedure for determining whether two protons are homotopic, enantiotopic, or not chemically equivalent

24) Protons Ha and Hb in the compound given are ________.

An illustration shows the structure of a compound. It has a cyclohexane ring, in which C 1 and C 4 are each wedge bonded to a methyl group. C 2 is dash bonded to H a atom and wedge bonded to H b atom.

A) homotopic

B) enantiotopic

C) diastereotopic

D) mesotopic

E) none of these

Diff: 2

Learning Objective: 15.4 Describe chemical equivalence and a procedure for determining whether two protons are homotopic, enantiotopic, or not chemically equivalent

25) Protons Ha and Hb in the compound given are ________.

An illustration shows the structure of a compound. It has a cyclohexane ring fused to a cyclopentane ring. There is a double bond between C 1 and C 2 of the cyclohexane ring. C 2 of the cyclopentane ring is bonded to H a atom and H b atom. C 5 of the cyclopentane ring is dash bonded to an N H 2 group.

A) homotopic

B) enantiotopic

C) diastereotopic

D) mesotopic

E) none of these

Diff: 2

Learning Objective: 15.4 Describe chemical equivalence and a procedure for determining whether two protons are homotopic, enantiotopic, or not chemically equivalent

26) Protons Ha and Hb in the compound given are ________.

An illustration shows the structure of a compound. It has a SMILES string of COc1ccc(cc1)OC, in which C 5 is bonded to H a atom and C 6 is bonded to H b atom.

A) homotopic

B) enantiotopic

C) diastereotopic

D) mesotopic

E) none of these

Diff: 2

Learning Objective: 15.4 Describe chemical equivalence and a procedure for determining whether two protons are homotopic, enantiotopic, or not chemically equivalent

27) How many signals would you expect in the 1H NMR spectrum of CH3OCH2CH3?

A) 1

B) 2

C) 3

D) 4

E) 5

Diff: 2

Learning Objective: 15.4 Describe chemical equivalence and a procedure for determining whether two protons are homotopic, enantiotopic, or not chemically equivalent

28) How many signals would you expect in the 1H NMR spectrum of CH3OCH2CH2OCH3?

A) 1

B) 2

C) 3

D) 4

E) 5

Diff: 2

Learning Objective: 15.4 Describe chemical equivalence and a procedure for determining whether two protons are homotopic, enantiotopic, or not chemically equivalent

29) How many signals would you expect in the 1H NMR spectrum of (CH3)2CHCH2CH2CH3?

A) 1

B) 2

C) 3

D) 4

E) 5

Diff: 2

Learning Objective: 15.4 Describe chemical equivalence and a procedure for determining whether two protons are homotopic, enantiotopic, or not chemically equivalent

30) How many signals would you expect in the 1H NMR spectrum of HOCH2CH2CH2CH2OH?

A) 1

B) 2

C) 3

D) 4

E) 5

Diff: 2

Learning Objective: 15.4 Describe chemical equivalence and a procedure for determining whether two protons are homotopic, enantiotopic, or not chemically equivalent

31) How many signals would you expect in the 1H NMR spectrum of the compound shown?

An illustration shows the structure of a compound that has a SMILES string of CCC=Cc1ccccc1.

A) 4

B) 5

C) 6

D) 7

E) 8

Diff: 2

Learning Objective: 15.4 Describe chemical equivalence and a procedure for determining whether two protons are homotopic, enantiotopic, or not chemically equivalent

32) How many signals would you expect in the 1H NMR spectrum of the compound shown?

An illustration shows the structure of a compound that has a SMILES string of CC(C)COC(=O)C(C)C.

A) 4

B) 5

C) 6

D) 7

E) 8

Diff: 2

Learning Objective: 15.4 Describe chemical equivalence and a procedure for determining whether two protons are homotopic, enantiotopic, or not chemically equivalent

33) How many signals would you expect in the 1H NMR spectrum of the compound shown?

An illustration shows the structure of a compound that has a SMILES string of CCc1cccc(c1)C(=O)O.

A) 4

B) 5

C) 6

D) 7

E) 9

Diff: 2

Learning Objective: 15.4 Describe chemical equivalence and a procedure for determining whether two protons are homotopic, enantiotopic, or not chemically equivalent

34) How many signals would you expect in the 1H NMR spectrum of the compound shown?

An illustration shows the structure of a compound. It has an eight carbon chain, in which C 2 and C 7 are each bonded to two methyl groups, C 4 is double bonded to an oxygen atom, and C 6 is replaced by an oxygen atom.

A) 3

B) 4

C) 5

D) 6

E) 7

Diff: 2

Learning Objective: 15.4 Describe chemical equivalence and a procedure for determining whether two protons are homotopic, enantiotopic, or not chemically equivalent

35) How many signals would you expect in the 1H NMR spectrum of the compound given?

An illustration shows the structure of a compound. It has a benzene ring, in which C 1 is bonded to a four carbon chain. C 1 and C 4 of the four carbon chain is double bonded to an oxygen atom each. C 4 of the four carbon chain is also single bonded to a chlorine atom. C 4 of the benzene ring is bonded to C 2 of a three carbon chain.

Diff: 2

Learning Objective: 15.4 Describe chemical equivalence and a procedure for determining whether two protons are homotopic, enantiotopic, or not chemically equivalent

36) How many signals would you expect in the 1H NMR spectrum of the compound given?

An illustration shows the structure of a compound that has a SMILES string of CCOc1ccc(cc1)OCC.

A) 3

B) 4

C) 5

D) 6

E) 7

Diff: 2

Learning Objective: 15.4 Describe chemical equivalence and a procedure for determining whether two protons are homotopic, enantiotopic, or not chemically equivalent

37) The 1H NMR spectrum of bromoethane shows a signal at 3.5 ppm when the spectrum is recorded using a 60 MHz spectrometer. Where do you expect to see the signal if a 300 MHz instrument is used instead?

A) 3.5 ppm

B) 7.5 ppm

C) 6.8 ppm

D) 5.8 ppm

E) none of these

Diff: 2

Learning Objective: 15.5 Define chemical shift, inductive effect, and anisotropic effect, and describe the signals produced by methyl, methylene, and methine groups

38) ________ is used as a reference for recording NMR spectra and is assigned a chemical shift value of zero.

A) Tetramethylsilene

B) 13C

C) Benzene

D) CCH4

E) CCl4

Diff: 1

Learning Objective: 15.5 Define chemical shift, inductive effect, and anisotropic effect, and describe the signals produced by methyl, methylene, and methine groups

39) Which of the indicated protons in the following compound would appear farthest downfield in the 1H NMR spectrum given?

An illustration shows the structure of a compound. It has a four carbon chain, in which C 4 is bonded to a hydroxyl group. An arrow labeled 1 (Roman numeral) points TOWARD C 1. An arrow labeled 2 (Roman numeral) points toward C 2. An arrow labeled 3 (Roman numeral) points TOWARD C 3. An arrow labeled 4 (Roman numeral) points TOWARD C 4.

A) I

B) II

C) III

D) IV

Diff: 2

Learning Objective: 15.5 Define chemical shift, inductive effect, and anisotropic effect, and describe the signals produced by methyl, methylene, and methine groups

40) Which of the indicated protons in the following compound would appear farthest upfield in the 1H NMR spectrum given?

An illustration shows the structure of a compound. It has a four carbon chain, in which C 4 is bonded to a hydroxyl group. An arrow labeled 1 (Roman numeral) points toward C 1. An arrow labeled 2 (Roman numeral) points toward C 2. An arrow labeled 3 (Roman numeral) points toward C 3. An arrow labeled 4 (Roman numeral) points toward C 4.

A) I

B) II

C) III

D) IV

Diff: 2

Learning Objective: 15.5 Define chemical shift, inductive effect, and anisotropic effect, and describe the signals produced by methyl, methylene, and methine groups

41) Which of the indicated protons in the compound given would appear farther downfield in the 1H NMR spectrum?

A) I

B) II

C) III

D) IV

E) V

Diff: 3

Learning Objective: 15.5 Define chemical shift, inductive effect, and anisotropic effect, and describe the signals produced by methyl, methylene, and methine groups

42) Which of the indicated protons in the following compound would appear farthest upfield in the 1H NMR spectrum?

A) I

B) II

C) III

D) IV

E) I and III

Diff: 3

Learning Objective: 15.5 Define chemical shift, inductive effect, and anisotropic effect, and describe the signals produced by methyl, methylene, and methine groups

43) Which of the following is the best prediction of the chemical shifts for the signals in the 1H NMR spectrum for the compound shown?

An illustration shows the structure of a compound. It has a four carbon chain, in which C 2 is double bonded to an oxygen atom and C 4 is bonded to a hydroxyl group. An arrow labeled 1 (Roman numeral) points toward C 4. An arrow labeled 2 (Roman numeral) points toward C 3. An arrow labeled 3 (Roman numeral) points toward C 1.

A) I = 3.7 ppm, II = 2.7 ppm, III = 1.9 ppm

B) I = 3.7 ppm, II = 2.2 ppm, III = 1.9 ppm

C) I = 3.9 ppm, II = 2.7 ppm, III = 1.9 ppm

D) I = 3.9 ppm, II = 2.2 ppm, III = 2.4 ppm

E) none of these

Diff: 2

Learning Objective: 15.5 Define chemical shift, inductive effect, and anisotropic effect, and describe the signals produced by methyl, methylene, and methine groups

44) Which of the choices given is the best prediction of the chemical shifts for the signals in the 1H NMR spectrum for the following compound?

An illustration shows the structure of a compound. It has a six carbon chain, in which C 2 and C 5 are each replaced by an oxygen atom. An arrow labeled 1 (Roman numeral) points toward C 1. An arrow labeled 2 (Roman numeral) points toward C 3. An arrow labeled 3 (Roman numeral) points toward C 4. An arrow labeled 4 (Roman numeral) points toward C 6.

A) I = 3.9 ppm, II = 4.2 ppm, III = 2.2 ppm, IV = 3.4 ppm

B) I = 3.4 ppm, II = 2.2 ppm, III = 2.2 ppm, IV = 3.4 ppm

C) I = 3.4 ppm, II = 2.2 ppm, III = 4.2 ppm, IV = 3.4 ppm

D) I = 3.4 ppm, II = 4.2 ppm, III = 4.2 ppm, IV = 3.4 ppm

E) none of these

Diff: 2

Learning Objective: 15.5 Define chemical shift, inductive effect, and anisotropic effect, and describe the signals produced by methyl, methylene, and methine groups

45) Which of the choices given is the best prediction of the chemical shifts for the signals in the 1H NMR spectrum for the following compound?

An illustration shows the structure of a compound. It has a six carbon chain, in which C 2 is double bonded to an oxygen atom and C 3 is replaced by an oxygen atom. An arrow labeled 1 (Roman numeral) points toward C 6. An arrow labeled 2 (Roman numeral) points toward C 5. An arrow labeled 3 (Roman numeral) points toward C 4. An arrow labeled 4 (Roman numeral) points toward C 1.

A) I = 0.9 ppm, II = 1.8 ppm, III = 4.2 ppm, IV = 1.9 ppm

B) I = 0.9 ppm, II = 1.2 ppm, III = 3.7 ppm, IV = 1.9 ppm

C) I = 0.9 ppm, II = 1.7 ppm, III = 3.4 ppm, IV = 2.4 ppm

D) I = 0.9 ppm, II = 1.7 ppm, III = 3.4 ppm, IV = 1.9 ppm

E) none of these

Diff: 2

Learning Objective: 15.5 Define chemical shift, inductive effect, and anisotropic effect, and describe the signals produced by methyl, methylene, and methine groups

46) Which of the choices given is the best prediction of the chemical shifts for the signals in the 1H NMR spectrum for the following compound?

A) I = 0.9 ppm, II = 2.7 ppm, III = 1.2 ppm, IV = 0.9 ppm

B) I = 1.1 ppm, II = 3.2 ppm, III = 1.4 ppm, IV = 0.9 ppm

C) I = 0.9 ppm, II = 1.7 ppm, III = 1.2 ppm, IV = 1.1 ppm

D) I = 0.9 ppm, II = 1.9 ppm, III = 3.4 ppm, IV = 0.9 ppm

E) none of these

Diff: 2

Learning Objective: 15.5 Define chemical shift, inductive effect, and anisotropic effect, and describe the signals produced by methyl, methylene, and methine groups

47) Predict the chemical shifts for the signals in the 1H NMR spectrum for the given compound.

A) I

B) II

C) III

D) IV

E) V

Diff: 3

Learning Objective: 15.5 Define chemical shift, inductive effect, and anisotropic effect, and describe the signals produced by methyl, methylene, and methine groups

48) Predict the chemical shifts for the signals in the 1H NMR spectrum for the following compound.

An illustration shows a compound, followed by five same compounds labeled 1 through 5 with their different chemical shift values. The compound has a nine carbon chain, in which C 2 and C 6 are each double bonded to an oxygen atom. C 5 is replaced by an oxygen atom.

A) I

B) II

C) III

D) IV

E) V

Diff: 3

Learning Objective: 15.5 Define chemical shift, inductive effect, and anisotropic effect, and describe the signals produced by methyl, methylene, and methine groups

49) Aromatic protons produce signals in the range of 7 — 8 ppm, due to the ________ effect of π electrons

A) diamagnetic anisotropy

B) paramagnetic anisotropy

C) diamagnetic isotropy

D) paramagnetic isotropy

E) none of these

Diff: 2

Learning Objective: 15.5 Define chemical shift, inductive effect, and anisotropic effect, and describe the signals produced by methyl, methylene, and methine groups

50) Which of the protons shown appear farthest upfield in the 1H NMR spectrum?

A) I

B) II

C) III

D) IV

E) none of these

Diff: 2

Learning Objective: 15.5 Define chemical shift, inductive effect, and anisotropic effect, and describe the signals produced by methyl, methylene, and methine groups

51) A compound with molecular formula C8H14 has the 1H NMR spectrum shown. Which choices shows the correct number of protons giving rise to each signal?

A) I — 3H, II — 9H, III — 2H

B) I — 2H, II — 9H, III — 3H

C) I — 4H, II — 6H, III — 4H

D) I — 3H, II — 6H, III — 2H

Diff: 2

Learning Objective: 15.6 Define integration, and explain what it indicates

52) A compound with molecular formula C6H11N has the 1H NMR spectrum shown. Which choices shows the correct number of protons giving rise to each signal?

A) I — 6H, II — 3H, III — 2H

B) I — 5H, II — 4H, III — 2H

C) I — 6H, II — 4H, III — 1H

D) I — 1H, II — 4H, III — 6H

Diff: 2

Learning Objective: 15.6 Define integration, and explain what it indicates

53) A compound with molecular formula C8H10O has the 1H NMR spectrum shown. Which of the choices shows the correct number of protons giving rise to each signal?

SDBS: National Institute of Advanced Industrial Science and Technology

Diff: 2

Learning Objective: 15.6 Define integration, and explain what it indicates

54) What is the structure of a molecule with that has an integration of 6H, 2H, 1H, and 1H?

A) CH3CH(OH)CH(CH3)2

B) CH3CH2OCH2CH3

C) CH3C(O)CH2CH2CH3

D) (CH3)2C(OH)CH3

E) (CH3)2CHCH2OH

Diff: 2

Learning Objective: 15.6 Define integration, and explain what it indicates

55) What is the structure of a molecule with that has an integration of 9H, 3H, 1H?

A) CH3CH2CH2CH2CH2CH2CH2CH2NH2

B) CH3)3CH2COOH

C) (CH3)3CH2COOH

D) (CH3)3CNHCH3

E) (CH3)2CHOCH2CH3

Diff: 2

Learning Objective: 15.6 Define integration, and explain what it indicates

56) What is the structure of a molecule that has an integration of 3H, 2H, 2H, and 2H?

A) CH3CH2COOCH2Br

B) CH3CH(Br)CH2CH3

C) BrCH2CH(CH3)CH2COOH

D) CH3CH2CH2CH2Br

E) ClCH2CH2CH2Br

Diff: 2

Learning Objective: 15.6 Define integration, and explain what it indicates

57) Which of the compounds shown gives a 1H NMR spectrum consisting of only a singlet?

A) 1,1-dichloropropane

B) 1,3-dichloropropane

C) 1,2-dichloropropane

D) 2,2-dichloropropane

E) 1-chloropropane

Diff: 2

Learning Objective: 15.7 Describe spin-spin splitting and multiplicity

58) How many 1H NMR signals does 2-chloro-3-methyl-2-butene exhibit? Assume both allylic methyl show as chemically equivalent in the NMR.

A) 1

B) 2

C) 3

D) 4

E) 5

Diff: 2

Learning Objective: 15.7 Describe spin-spin splitting and multiplicity

59) Which of the compounds shown displays two triplets and a singlet in its 1H NMR spectrum?

A) CH3CH(OCH3)2

B) CH3OCH2CH2OCH3

C) CH3OCH2CH(OH)CH3

D) CH3OCH2CH2CH2CH2OCH3

E) CH3CH2OCH2CH3

Diff: 2

Learning Objective: 15.7 Describe spin-spin splitting and multiplicity

60) Which of the compounds shown displays only two singlets in its 1H NMR spectrum?

A) I

B) II

C) III

D) IV

E) V

Diff: 2

Learning Objective: 15.7 Describe spin-spin splitting and multiplicity

61) Which of the compounds shown displays only one singlets in its 1H NMR spectrum?

A) I

B) II

C) III

D) IV

E) V

Diff: 2

Learning Objective: 15.7 Describe spin-spin splitting and multiplicity

62) Which of the compounds shown displays a singlet, a triplet and a quartet in its 1H NMR spectrum?

A) 2-chloro-4-methylpentane

B) 3-chloro-2-methylpentane

C) 3-chloropentane

D) 1-chloro-2,2-dimethylbutane

E) 3-chloro-3-methylpentane

Diff: 2

Learning Objective: 15.7 Describe spin-spin splitting and multiplicity

63) Determine the multiplicity of each signal in the expected 1H NMR spectrum of the compound shown.

An illustration shows a compound that has a SMILES string of CCOC(C)C.

A) I

B) II

C) III

D) IV

E) V

Diff: 3

Learning Objective: 15.7 Describe spin-spin splitting and multiplicity

64) Determine the multiplicity of each signal in the expected 1H NMR spectrum of the compound shown.

An illustration shows a compound that has a SMILES string of CCCC(=O)NCC(C)(C)C.

A) I

B) II

C) III

D) IV

E) V

Diff: 3

Learning Objective: 15.7 Describe spin-spin splitting and multiplicity

65) Determine the multiplicity of each signal in the expected 1H NMR spectrum of the following compound.

An illustration shows a compound that has a SMILES string of CC(C)CC(=O)OC.

A) I

B) II

C) III

D) IV

E) V

Diff: 3

Learning Objective: 15.7 Describe spin-spin splitting and multiplicity

66) Determine the multiplicity of each signal in the expected 1H NMR spectrum of the following compound.

An illustration shows a compound, followed by five same compounds labeled 1 through 5 with their different chemical shift values. The compound has a seven carbon chain, in which C 1 is double bonded to an oxygen atom and single bonded to a hydrogen atom, C 3 is bonded to a methyl group, C 4 is double bonded to an oxygen atom, and C 6 is bonded to two methyl groups.

A) I

B) II

C) III

D) IV

E) V

Diff: 3

Learning Objective: 15.7 Describe spin-spin splitting and multiplicity

67) Determine the multiplicity of each signal in the expected 1H NMR spectrum of the following compound.

An illustration shows the structure of a compound. It has a five carbon chain, in which C 1 is double bonded to an oxygen atom and single bonded to a hydroxyl group, C 4 is replaced by an oxygen atom, and C 5 is bonded to an N H 2 group.

A) I

B) II

C) III

D) IV

E) V

Diff: 3

Learning Objective: 15.7 Describe spin-spin splitting and multiplicity

68) Predict the multiplicity of each signal in the expected 1H NMR spectrum of 2,3-dimethyl-2-pentanol.

A) I

B) II

C) III

D) IV

E) V

Diff: 3

Learning Objective: 15.7 Describe spin-spin splitting and multiplicity

69) Determine the multiplicity of each signal in the expected 1H NMR spectrum of the following compound.

An illustration shows a compound that has a SMILES string of CC(C)c1ccc(cc1)OC.

A) I

B) II

C) III

D) IV

E) V

Diff: 3

Learning Objective: 15.7 Describe spin-spin splitting and multiplicity

70) The coupling constant (J) for bromoethane is 7 Hz when the 1H NMR spectrum is acquired at 250 MHz. What is the coupling constant between these protons when the spectrum is acquired at 500 MHz?

A) 3.5 Hz

B) 7 Hz

C) 14 Hz

D) 21 Hz

E) 1 Hz

Diff: 3

Learning Objective: 15.7 Describe spin-spin splitting and multiplicity

71) Which of the following is the maximum multiplicity observed for Hc protons in the compound shown? Assume that the Jcd and Jcb values are different.

An illustration shows the structure of a compound. It has a five carbon chain, in which C 2 is replaced by an N H group. C 1 is labeled a, C 3 is labeled b, C 4 is labeled c, and C 5 is labeled d.

A) 5

B) 6

C) 8

D) 12

E) none of these

Diff: 3

Learning Objective: 15.7 Describe spin-spin splitting and multiplicity

72) Which of the following is the maximum multiplicity observed for Hb protons in the compound shown? Assume that the Jab and Jbc values are different.

An illustration shows the structure of a compound. It has a five carbon chain, in which C 2 is bonded to a methyl group and C 4 is replaced by an oxygen atom. C 1 is labeled a, the methyl group bonded to C 2 is labeled a, C 2 is labeled b, C 3 is labeled c, and C 5 is labeled d.

A) 9

B) 12

C) 21

D) 24

E) none of these

Diff: 2

Learning Objective: 15.7 Describe spin-spin splitting and multiplicity

73) Which of the following Jab values is consistent with the structure shown?

An illustration shows the structure of a compound. It has a five carbon chain, in which C 1 is bonded to H c atom and H b atom, C 1 is double bonded to C 2, C 2 is bonded to H a atom, C 3 is replaced by an oxygen atom, C 4 is double bonded to an oxygen atom.

A) 1.2 Hz

B) 6.5 Hz

C) 17 Hz

D) 20 Hz

E) 11 Hz

Diff: 3

Learning Objective: 15.7 Describe spin-spin splitting and multiplicity

74) Which of the following Jac values is consistent with the structure shown?

A) 1.2 Hz

B) 6.5 Hz

C) 17 Hz

D) 20 Hz

E) 11 Hz

Diff: 3

Learning Objective: 15.7 Describe spin-spin splitting and multiplicity

75) Which of the following Jbc values is consistent with the structure shown?

A) 1.2 Hz

B) 6.5 Hz

C) 14 Hz

D) 20 Hz

E) none of these

Diff: 3

Learning Objective: 15.7 Describe spin-spin splitting and multiplicity

76) Presence of which of the following protons is confirmed by D2O exchange?

A) OH

B) NH2

C) CH

D) A & B

E) none of these

Diff: 2

Learning Objective: 15.7 Describe spin-spin splitting and multiplicity

77) The 1H NMR spectrum of 1-propanol displays a singlet for the OH proton instead of a triplet. Explain why.

A) This is typical of all protons bound to oxygen.

B) 1-propanol is too small for coupling to occur.

C) 1-propanol molecules rapidly exchange the OH proton, which prevents splitting.

D) The signal for the OH proton is out of the normal range of the 1H NMR spectrum, meaning that it is not usually visible.

E) OH does not generate a proton signal due to the highly electronegative nature of oxygen.

Diff: 2

Learning Objective: 15.7 Describe spin-spin splitting and multiplicity

78) Ethanamine (CH3CH2NH2) experiences a rapid exchange of NH2 protons. How do you predict that this affects the 1H NMR spectrum? of ethanamine?

A) Like other molecules with nitrogen, the electronegativity of nitrogen prevents NH2 protons from producing a signal.

B) NH2 protons are exchanged too rapidly for splitting to occur, so a singlet is produced.

C) Like many other molecules with NH2, ethanamine is highly unstable and produces a variable proton NMR signal.

D) The NH2 protons should produce a standard NMR signal despite this rapid exchange.

E) The effects on the NMR spectrum depend on whether an oxygen is nearby, so it is impossible to predict whether the rapid exchange would affect their signal.

Diff: 3

Learning Objective: 15.7 Describe spin-spin splitting and multiplicity

79) How would the 1H NMR spectrum of an alcohol be affected by the addition of D2O to replace the OH protons with D atoms?

A) The chemical shift of the absorption would move to the left.

B) The chemical shift of the absorption would move to the right.

C) The OH absorption would disappear.

D) The absorption would become a narrow, rather than a broad, peak.

E) The absorption would become a broad, rather than a narrow, peak.

Diff: 3

Learning Objective: 15.7 Describe spin-spin splitting and multiplicity

80) Determine the multiplicity and predict the chemical shifts of the four signals in the expected 1H NMR spectrum of the following compound.

An illustration shows the structure of a compound. It has a six carbon chain, in which C 4 is replaced by an oxygen atom, and C 5 is double bonded to an oxygen atom. C 1 is labeled 1, C 2 is labeled 2, C 3 is labeled 3, and C 6 is labeled 4.

A) I

B) II

C) III

D) IV

Diff: 2

Learning Objective: 15.8 Draw the expected 1H NMR spectrum of a compound

81) Determine the multiplicity and predict the chemical shifts of each signal in the expected 1H NMR spectrum of the following compound.

An illustration shows the structure of a compound. It has an eight carbon chain, in which C 2 is bonded to a methyl group, C 3 and C 5 are each double bonded to an oxygen atom, and C 4 is replaced by an oxygen atom.

A) I

B) II

C) III

D) IV

E) V

Diff: 2

Learning Objective: 15.8 Draw the expected 1H NMR spectrum of a compound

82) Determine the multiplicity and predict the chemical shifts of each signal in the expected 1H NMR spectrum of the following compound.

An illustration shows the structure of a compound. It has a cyclohexane ring, in which C 4 is bonded to a two carbon chain, C 2 and C 5 are each replaced by an oxygen atom, and C 1 is double bonded to an oxygen atom. C 1 of the two carbon chain is double bonded to an oxygen atom.

A) I

B) II

C) III

D) IV

Diff: 2

Learning Objective: 15.8 Draw the expected 1H NMR spectrum of a compound

83) How would you use 1H NMR spectroscopy to distinguish between the two compounds shown?

An illustration shows the structure of two compounds. The first compound labeled 1 has a SMILES string of CC(=O)CC(C)(C)C=O. The second compound labeled 2 has a SMILES string of CC(C)(C)C(=O)CC=O.

A) I = 3 and II = 2 signals

B) I = 4 and II = 3 signals

C) I = 5 and II = 3 signals

D) I = 5 and II = 4 signals

E) I = 3 and II = 4 signals

Diff: 2

Learning Objective: 15.9 Distinguish between compounds using 1H NMR spectroscopy

84) How would you use 1H NMR spectroscopy to distinguish between the two compounds shown?

An illustration shows the structure of two compounds. The first compound labeled 1 has a SMILES string of CCOCOCC. The second compound labeled 2 has a SMILES string of COCCCOC.

A) The compounds will have different numbers of signals.

B) Compound II will have a singlet with a higher chemical shift.

C) Compound I will have a triplet, a quartet, and a singlet.

D) Compound II will have a singlet, a triplet, and a quintet.

E) C and D are correct.

Diff: 2

Learning Objective: 15.9 Distinguish between compounds using 1H NMR spectroscopy

85) How would you use 1H NMR spectroscopy to distinguish between the following compounds?

An illustration shows the structure of two compounds. The first compound labeled 1 has a SMILES string of CCCC(=O)OC(C)C. The second compound labeled 2 has a SMILES string of CCOC(=O)CC(C)C.

A) The compounds will have different numbers of signals.

B) Compound I will have a doublet, a septet, two triplets, and a sextet.

C) Compound I will have two doublets, two triplets, and a multiplet.

D) Compound II will have a doublet, a multiplet, a quartet, and a triplet.

E) Both compounds will have almost identical signals but only compound I will have a multiplet.

Diff: 2

Learning Objective: 15.9 Distinguish between compounds using 1H NMR spectroscopy

86) How would you use 1H NMR spectroscopy to distinguish between the following compounds?

An illustration shows the structure of two compounds. The first compound labeled 1 has a SMILES string of CC(C)OC(=O)c1ccccc1. The second compound labeled 2 has a SMILES string of CC(C)C(=O)Oc1ccccc1.

A) The compounds will have different numbers of signals.

B) The proton bonded to C bonded to 2 CH3 to the right will be farther downfield in the spectrum of compound I versus the spectrum of compound II.

C) The protons bonded to the aromatic ring will all have the same chemical shift in the spectrum of compound I but will differ in the spectrum of compound II.

D) The entire spectrum of compound I will be shifted downfield from the spectrum of compound II.

E) The spectra will be identical, so the compounds cannot be distinguished based solely on their NMR spectra.

Diff: 2

Learning Objective: 15.10 Describe the steps in the analysis of a 1H NMR spectrum

87) A compound with a molecular formula C9H12 has the 1H NMR spectrum below. Which structures given is consistent with this spectrum?

An illustration shows the structure of four compounds. The first compound labeled 1 has a SMILES string of Cc1ccc(c(c1)C)C. The second compound labeled 2 has a SMILES string of Cc1cccc(c1C)C. The third compound labeled 3 has a SMILES string of Cc1cc(cc(c1)C)C. The fourth compound labeled 4 has a SMILES string of CC(C)(C)c1ccccc1.

A) I

B) II

C) III

D) IV

E) none of these

Diff: 2

Learning Objective: 15.10 Describe the steps in the analysis of a 1H NMR spectrum

88) Which of the structures given is consistent with this 1H NMR spectrum?

SDBS: National Institute of Advanced Industrial Science and Technology

An illustration shows the structure of four compounds. The first compound labeled 1 has a SMILES string of COC(=O)c1ccccc1. The second compound labeled 2 has a SMILES string of CC(=C)c1ccccc1. The third compound labeled 3 has a SMILES string of CCC(=O)c1ccccc1. The fourth compound labeled 4 has a SMILES string of CCc1ccccc1.

A) I

B) II

C) III

D) IV

E) none of these

Diff: 2

Learning Objective: 15.10 Describe the steps in the analysis of a 1H NMR spectrum

89) A compound with a molecular formula C9H10O2 has the 1H NMR spectrum shown. Which of the structures given is consistent with this spectrum?

An illustration shows the structure of four compounds. The first compound labeled 1 has a SMILES string of c1ccc(cc1)CCOC=O. The second compound labeled 2 has a SMILES string of c1ccc(cc1)CCC(=O)O. The third compound labeled 3 has a SMILES string of c1ccc(cc1)C(=O)CCO. The fourth compound labeled 4 has a SMILES string of COC(=O)Cc1ccccc1.

A) I

B) II

C) III

D) IV

E) none of these

Diff: 2

Learning Objective: 15.10 Describe the steps in the analysis of a 1H NMR spectrum

90) A compound with a molecular formula C8H15ClO3 has the 1H NMR spectrum given. The IR spectrum shows a strong absorption at 1800 cm-1. Which of the structures shown is consistent with this spectrum?

A) I

B) II

C) III

D) IV

E) none of these

Diff: 2

Learning Objective: 15.10 Describe the steps in the analysis of a 1H NMR spectrum

91) A compound with a molecular formula C5H11NO has the 1H NMR spectrum given. The IR spectrum shows an absorption at around 3400 cm-1. Which of the structures given is consistent with this spectrum?

An illustration shows the structure of four compounds. The first compound labeled 1 has a SMILES string of CCC(=O)NCC. The second compound labeled 2 has a SMILES string of CCCC(=O)NC. The third compound labeled 3 has a SMILES string of CCCNC(=O)C. The fourth compound labeled 4 has a SMILES string of CCCCNC=O.

A) I

B) II

C) III

D) IV

E) none of these

Diff: 2

Learning Objective: 15.10 Describe the steps in the analysis of a 1H NMR spectrum

92) A compound with a molecular formula of C5H10O has the 1H NMR spectrum shown. Which structure shown is consistent with this spectrum?

An illustration shows the proton N M R spectrum of a compound with a molecular formula, C 5 H 10 O. The horizontal axis plots parts per million, p p m and has a decreasing scale from left to right ranging from 1 to 0, in increments of 1. The spectrum shows two peaks. The first peak labeled 9 is at 1.2 p p m. The second peak labeled 1 is at 9.5 p p m.

An illustration shows the structure of five compounds. The first compound labeled 1 has a SMILES string of CC(C)(C)C=O. The second compound labeled 2 has a SMILES string of CC(C)(C)CO. The third compound labeled 3 has a SMILES string of CC(=C)CO. The fourth compound labeled 4 has a SMILES string of CC(=C)C=O. The fifth compound labeled 5 has a SMILES string of CC(C)(C)C(O)O.

A) I

B) II

C) III

D) IV

E) V

Diff: 2

Learning Objective: 15.10 Describe the steps in the analysis of a 1H NMR spectrum

93) Propose a structure for a compound, with molecular formula C5H11Cl, that fits the following spectroscopic data:

1H NMR: 0.9 δ (triplet, 3H), 1.3 δ (sextet, 2H), 1.5 δ (quartet, 2H), 1.6 δ (doublet, 3H), 3.6 δ (sextet, 1H)

An illustration shows the structure of five compounds. The first compound labeled 1 has a SMILES string of CCC(CC)Cl. The second compound labeled 2 has a SMILES string of CCCC(C)Cl. The third compound labeled 3 has a SMILES string of CC(C)C(C)Cl. The fourth compound labeled 4 has a SMILES string of CC(C)C(C)Cl. The fifth compound labeled 5 has a SMILES string of CC(C)(C)CCl.

A) I

B) II

C) III

D) IV

E) V

Diff: 2

Learning Objective: 15.10 Describe the steps in the analysis of a 1H NMR spectrum

94) Propose a structure for a compound, with molecular formula C8H14O3, that fits the following spectroscopic data:

IR: 1820cm-1, 1760cm-1

1H NMR: 1.0 δ (triplet, 6H), 1.6 δ (sextet, 4H), 2.2 δ (triplet, 4H)

A) I

B) II

C) III

D) IV

E) V

Diff: 2

Learning Objective: 15.10 Describe the steps in the analysis of a 1H NMR spectrum

95) Propose a structure for a compound, with molecular formula C10H12O, that fits the following spectroscopic data:

IR: 1680 cm-1

1H NMR: 1.0 δ (triplet, 3H), 1.5 δ (sextet, 2H), 2.6 δ (triplet, 2H), 7.4 δ (triplet, 2H), 7.5 δ (triplet, 1H), 7.9 δ (doublet, 2H)

A) I

B) II

C) III

D) IV

E) V

Diff: 2

Learning Objective: 15.10 Describe the steps in the analysis of a 1H NMR spectrum

96) A compound with a molecular formula of C8H16O has the following 1H NMR spectrum. Provide a structure that is consistent with this spectrum.

An illustration shows the structure of five compounds. The first compound labeled 1 has a SMILES string of CCCC(=O)CC(C)C. The second compound labeled 2 has a SMILES string of CCC(=O)CCC(C)C. The third compound labeled 3 has a SMILES string of CCC(=O)CCC(C)C. The fourth compound labeled 4 has a SMILES string of CCC(C)CC(=O)CC. The fifth compound labeled 5 has a SMILES string of CCCCC(=O)C(C)C.

A) I

B) II

C) III

D) IV

E) V

Diff: 2

Learning Objective: 15.10 Describe the steps in the analysis of a 1H NMR spectrum

97) A compound with a molecular formula of C10H12O2 has the following 1H NMR spectrum. Which of the structures shown is consistent with this spectrum?

An illustration shows the structure of four compounds. The first compound labeled 1 has a SMILES string of CCCOc1ccc(cc1)C=O. The second compound labeled 2 has a SMILES string of CCCC(=O)Oc1ccccc1. The third compound labeled 3 has a SMILES string of CCC(=O)CCC(C)C. The fourth compound labeled 4 has a SMILES string of CCCC1=CC=CC=C1C(=O)O.

A) I

B) II

C) III

D) IV

E) none of these

Diff: 2

Learning Objective: 15.10 Describe the steps in the analysis of a 1H NMR spectrum

98) The broadband decoupling in 13C NMR suppresses ________ splitting.

A) 12C-13C

B) 12C-1H

C) 13C-13C

D) 13C-1H

E) none of these

Diff: 1

Learning Objective: 15.11 Describe how signal averaging and broadband decoupling are important in 13C NMR spectroscopy

99) The off-resonance decoupling in 13C NMR allows for ________ splitting.

A) 12C-13C

B) 12C-1H

C) 13C-13C

D) 13C-1H

E) none of these

Diff: 1

Learning Objective: 15.11 Describe how signal averaging and broadband decoupling are important in 13C NMR spectroscopy

100) Identify the splitting pattern for a CH3 in an off-resonance decoupled 13C NMR spectrum.

A) no peak

B) singlet

C) doublet

D) triplet

E) quartet

Diff: 1

Learning Objective: 15.11 Describe how signal averaging and broadband decoupling are important in 13C NMR spectroscopy

101) Identify the splitting pattern for a CH2 in an off-resonance decoupled 13C NMR spectrum.

A) no peak

B) singlet

C) doublet

D) triplet

E) quartet

Diff: 1

Learning Objective: 15.11 Describe how signal averaging and broadband decoupling are important in 13C NMR spectroscopy

102) Identify the splitting pattern for a CH in an off-resonance decoupled 13C NMR spectrum.

A) no peak

B) singlet

C) doublet

D) triplet

E) quartet

Diff: 1

Learning Objective: 15.11 Describe how signal averaging and broadband decoupling are important in 13C NMR spectroscopy

103) Identify the splitting pattern for a C in a carbonyl group in an off-resonance decoupled 13C NMR spectrum.

A) no peak

B) singlet

C) doublet

D) triplet

E) quartet

Diff: 1

Learning Objective: 15.11 Describe how signal averaging and broadband decoupling are important in 13C NMR spectroscopy

104) How many signals would you expect to find in the 13C NMR spectrum of the compound shown?

An illustration shows a compound that has a SMILES string of CCCC(=O)CC(C)C.

A) 6

B) 7

C) 8

D) 9

E) 10

Diff: 1

Learning Objective: 15.12 Explain what is revealed by the number of signals and their general location in a 13C NMR spectrum

105) How many signals would you expect to find in the 13C NMR spectrum of the compound shown?

An illustration shows a compound that has a SMILES string of C1CC(=O)CC(=O)C1.

A) 2

B) 3

C) 4

D) 5

E) 6

Diff: 2

Learning Objective: 15.12 Explain what is revealed by the number of signals and their general location in a 13C NMR spectrum

106) How many signals would you expect to find in the 13C NMR spectrum of the compound shown?

An illustration shows a compound that has a SMILES string of CC(=C(C)c1ccccc1)C.

A) 6

B) 7

C) 8

D) 9

E) 10

Diff: 2

Learning Objective: 15.12 Explain what is revealed by the number of signals and their general location in a 13C NMR spectrum

107) How many signals would you expect to find in the 13C NMR spectrum of the compounds shown?

An illustration shows the structure of two compounds. The first compound labeled 1 has a SMILES string of C2CCC1(CCCCO1)OC2. The second compound labeled 2 has a SMILES string of CCc1ccc(cc1)Cl.

A) I — 5, II — 8

B) I — 3, II — 6

C) I — 4, II — 8

D) I — 5, II — 6

E) I — 3, II — 3

Diff: 1

Learning Objective: 15.12 Explain what is revealed by the number of signals and their general location in a 13C NMR spectrum

108) Which of the carbon atoms shown displays the signal that is the most downfield in the 13C NMR spectrum?

A) I

B) II

C) III

D) IV

E) V

Diff: 2

Learning Objective: 15.12 Explain what is revealed by the number of signals and their general location in a 13C NMR spectrum

109) Which of the compounds shown displays four signals in its 13C NMR spectrum?

A) 2,6-dimethylheptane

B) 2,4-dimethylheptane

C) 3,5-dimethylheptane

D) 4,4-dimethylheptane

E) 3,4-dimethylheptane

Diff: 2

Learning Objective: 15.12 Explain what is revealed by the number of signals and their general location in a 13C NMR spectrum

110) Which of the compounds shown displays five signals in its 13C NMR spectrum?

A) I

B) II

C) III

D) IV

E) V

Diff: 2

Learning Objective: 15.12 Explain what is revealed by the number of signals and their general location in a 13C NMR spectrum

111) Which of the 13C NMR chemical shifts shown corresponds to Ca in the given compound?

An illustration shows a compound that has a SMILES string of CCOc1ccccc1. An arrow labeled a points toward C 1.

A) 100 — 150 ppm

B) 200 — 220 ppm

C) 60 — 90 ppm

D) 45 — 60 ppm

E) 45 — 80 ppm

Diff: 2

Learning Objective: 15.12 Explain what is revealed by the number of signals and their general location in a 13C NMR spectrum

112) Which of the compounds shown is consistent with the given 13C NMR spectrum?

A) I

B) II

C) III

D) IV

E) V

Diff: 3

Learning Objective: 15.12 Explain what is revealed by the number of signals and their general location in a 13C NMR spectrum

113) Which of the compounds shown is consistent with the 13C NMR spectrum given?

An illustration shows the carbon 13 N M R spectrum of a compound. The horizontal axis plots parts per million, p p m and has a decreasing scale from left to right ranging from 85 to 0, in increments of 5. The spectrum shows three peaks. The first peak is at 8 p p m. The second peak is at 30 p p m. The third peak is at 76 p p m.

An illustration shows the structure of five compounds. The first compound labeled 1 has a SMILES string of CCCC(C)O. The second compound labeled 2 has a SMILES string of CCC(C)(C)O. The third compound labeled 3 has a SMILES string of CC(C)C(C)O. The fourth compound labeled 4 has a SMILES string of CCC(CC)O. The fifth compound labeled 5 has a SMILES string of CCC(C(C)C)O.

A) I

B) II

C) III

D) IV

E) V

Diff: 3

Learning Objective: 15.12 Explain what is revealed by the number of signals and their general location in a 13C NMR spectrum

114) Which of the compounds shown is consistent with the 13C NMR spectrum given?

An illustration shows the carbon 13 N M R spectrum of a compound. The horizontal axis plots parts per million, p p m and has a decreasing scale from left to right ranging from 60 to 0, in increments of 5. The spectrum shows three peaks. The first peak is at 19 p p m. The second peak is at 32 p p m. The third peak is at 54 p p m.

An illustration shows the structure of five compounds. The first compound labeled 1 has a SMILES string of CCC(C)Cl. The second compound labeled 2 has a SMILES string of CC(C)(C)Cl. The third compound labeled 3 has a SMILES string of CC(C)CCl. The fourth compound labeled 4 has a SMILES string of CC(C)C(C)Cl. The fifth compound labeled 5 has a SMILES string of CCC(C)(C)Cl.

A) I

B) II

C) III

D) IV

E) V

Diff: 3

Learning Objective: 15.12 Explain what is revealed by the number of signals and their general location in a 13C NMR spectrum

115) Which of the compounds shown is consistent with the 13C NMR spectrum given?

An illustration shows the carbon 13 N M R spectrum of a compound. The horizontal axis plots parts per million, p p m and has a decreasing scale from left to right ranging from 85 to 0, in increments of 5. The spectrum shows four peaks. The first peak is at 16 p p m. The second peak is at 20 p p m. The third peak is at 36 p p m. The fourth peak is at 75 p p m.

An illustration shows the structure of five compounds. The first compound labeled 1 has a SMILES string of CCCC(C)O. The second compound labeled 2 has a SMILES string of CC(C)(C)CO. The third compound labeled 3 has a SMILES string of CC(C)C(C)O. The fourth compound labeled 4 has a SMILES string of CCC(CC)O. The fifth compound labeled 5 has a SMILES string of CCC(C(C)C)O.

A) I

B) II

C) III

D) IV

E) V

Diff: 3

Learning Objective: 15.12 Explain what is revealed by the number of signals and their general location in a 13C NMR spectrum

116) Which of the atoms or compounds shown displays a signal in the DEPT-90 13C NMR spectroscopy?

A) CH3

B) CH2

C) CH

D) C

E) none of these

Diff: 1

Learning Objective: 15.13 Describe what can be learned from DEPT C NMR spectroscopy

117) Which of the following atoms or compounds displays a negative signal in the DEPT-135 13C NMR spectroscopy?

A) CH3

B) CH2

C) CH

D) C

E) none of these

Diff: 1

Learning Objective: 15.13 Describe what can be learned from DEPT C NMR spectroscopy

118) Which of the following compounds or atoms does not display a signal in the DEPT-135 13C NMR spectroscopy?

A) CH3

B) CH2

C) CH

D) C

E) none of these

Diff: 1

Learning Objective: 15.13 Describe what can be learned from DEPT C NMR spectroscopy

119) Which of the following atoms or compounds does not display a signal in the DEPT-90, but displays a positive signal in DEPT-135 13C NMR spectroscopy?

A) CH3

B) CH2

C) CH

D) C

E) none of these

Diff: 1

Learning Objective: 15.13 Describe what can be learned from DEPT C NMR spectroscopy

120) Which of the compounds shown does not display a carbonyl carbon signal in the DEPT-90 and DEPT-135 13C NMR spectroscopy?

An illustration shows the structure of three compounds. The first compound labeled 1 has a SMILES string of CCC=O. The second compound labeled 2 has a SMILES string of CC(=O)OC. The third compound labeled 3 has a SMILES string of CC(=O)NC.

A) I

B) II

C) III

D) II and III

E) I and II

Diff: 2

Learning Objective: 15.13 Describe what can be learned from DEPT C NMR spectroscopy

121) A compound with the molecular formula C5H10Br2 displays the 13C NMR spectrum along with DEPT-90 and DEPT-135 13C NMR spectra. What is the structure for this compound?

A) Br2CHCH2CH2CH2CH3

B) BrCH2CH2CH2CH2CH2Br

C) (CH3)3CCHBr2

D) (CH3)2CHCH2CBr2

E) BrCH2CH(Br)CH2CH2CH3

Diff: 3

Learning Objective: 15.13 Describe what can be learned from DEPT C NMR spectroscopy

122) A compound, with molecular formula C7H7Br, displays the 13C NMR spectrum shown along with the DEPT-90 and DEPT-135 13C NMR spectra. What is the structure for this compound?

An illustration shows the structure of five compounds. The first compound labeled 1 has a SMILES string of Cc1ccc(cc1)Br. The second compound labeled 2 has a SMILES string of Cc1ccc(c(c1)Br)C. The third compound labeled 3 has a SMILES string of CC1CCC(CC1)Br. The fourth compound labeled 4 has a SMILES string of C=C1CC=C(C=C1)Br. The fifth compound labeled 5 has a SMILES string of CC1=CCC(C=C1)Br.

A) I

B) II

C) III

D) IV

E) V

Diff: 3

Learning Objective: 15.13 Describe what can be learned from DEPT C NMR spectroscopy

123) A compound, with molecular formula C4H9Br, displays the 1H NMR spectrum shown and 13C NMR spectra. Propose a structure for this compound.

An illustration shows the proton N M R spectrum of a compound with a molecular formula, C 4 H 9 B r. The horizontal axis plots parts per million, p p m and has a decreasing scale from left to right ranging from 3 to 0, in increments of 0.5. The spectrum shows one signal represented by a peak. This peak is at 1.8 p p m.

An illustration shows the carbon 13 N M R spectrum of a compound having the molecular formula, C 4 H 9 B r. The horizontal axis plots parts per million, p p m and has a decreasing scale from left to right ranging from 45 to 0, in increments of 5. The carbon 13 spectrum shows two peaks. The first tight group of two peaks is at 33 p p m. The second tight group of two peaks is present at 39.5 p p m.

An illustration shows the structure of five compounds. The first compound labeled 1 has a SMILES string of CCCBr. The second compound labeled 2 has a SMILES string of CCC(C)Br. The third compound labeled 3 has a SMILES string of CC(C)(C)Br. The fourth compound labeled 4 has a SMILES string of CC(C)C(C)Br. The fifth compound labeled 5 has a SMILES string of CC(C)C(C)Br.

A) I

B) II

C) III

D) IV

E) V

Diff: 2

Learning Objective: 15.9 Distinguish between compounds using 1H NMR spectroscopy

124) Which of the compounds shown, all with the molecular formula C9H18O2, is consistent with the 1H NMR and 13C NMR spectra given?

An illustration shows the structure of four compounds. The first compound labeled 1 has a SMILES string of CCC(CC)C(=O)OC(C)C. The second compound labeled 2 has a SMILES string of CC(C)CCC(=O)OC(C)C. The third compound labeled 3 has a SMILES string of CCC(CC)OC(=O)C(C)C. The fourth compound labeled 4 has a SMILES string of CC(C)CC(=O)OCC(C)C.

A) I

B) II

C) III

D) IV

E) None of these

Diff: 2

Learning Objective: 15.9 Distinguish between compounds using 1H NMR spectroscopy

125) Which of the given compounds, all with molecular formula C9H12O, is consistent with the 1H NMR and 13C NMR spectra shown?

An illustration shows the structure of four compounds. The first compound labeled 1 has a SMILES string of CCc1ccc(cc1)OC. The second compound labeled 2 has a SMILES string of CCc1ccc(cc1)CO. The third compound labeled 3 has a SMILES string of CCCc1ccc(cc1)O. The fourth compound labeled 4 has a SMILES string of CCOc1ccc(cc1)C.

A) I

B) II

C) III

D) IV

E) None of these

Diff: 2

Learning Objective: 15.9 Distinguish between compounds using 1H NMR spectroscopy

126) A compound with molecular formula C11H14O displays the following IR, 1H NMR and 13C NMR spectra. Which of the given structures is consistent with this data?

A) I

B) II

C) III

D) IV

E) V

Diff: 3

Learning Objective: 15.9 Distinguish between compounds using 1H NMR spectroscopy

127) A compound with molecular formula C7H14O2 displays the following IR, 1H NMR and 13C NMR spectra. What is a likely structure for this compound?

A) I

B) II

C) III

D) IV

E) V

Diff: 2

Learning Objective: 15.9 Distinguish between compounds using 1H NMR spectroscopy

128) A compound, with molecular formula C5H7NO2, displays the following IR, 1H NMR and 13C NMR spectra. What is a likely structure for this compound?

SDBS: National Institute of Advanced Industrial Science and Technology

A) I

B) II

C) III

D) IV

E) V

Diff: 3

Learning Objective: 15.9 Distinguish between compounds using 1H NMR spectroscopy

129) Which compound with the molecular formula C5H10O fits the spectroscopic data given?

IR: 1720 cm-1

1H NMR: 1.1 δ (doublet, 6H), 2.1 δ (singlet, 3H), 2.7 δ (septet, 1H)

13C NMR: 15, 22, 45, 210

An illustration shows the structure of five compounds. The first compound labeled 1 has a SMILES string of CC(C)C(C)O. The second compound labeled 2 has a SMILES string of CC(=O)C=C. The third compound labeled 3 has a SMILES string of CC(=C(C)O)C. The fourth compound labeled 4 has a SMILES string of CC(C)C(=O)C. The fifth compound labeled 5 has a SMILES string of CCC(=O)CC.

A) I

B) II

C) III

D) IV

E) V

Diff: 2

Learning Objective: 15.9 Distinguish between compounds using 1H NMR spectroscopy

130) Which compound with the molecular formula C8H19N fits the spectroscopic data given?

IR: 3400 cm-1

1H NMR: 0.9 δ (triplet, 6H), 1.1 δ (singlet, 1H, exchanges with D2O), 1.3 δ (sextet, 4H), 1.4 δ (quintet, 4H), 2.6 δ (triplet, 4H)

13C NMR: 13.7, 20.5, 30.4, 49.2

A) I

B) II

C) III

D) IV

E) V

Diff: 2

Learning Objective: 15.9 Distinguish between compounds using 1H NMR spectroscopy

131) What is a structure for a compound with molecular formula C5H12O2, that fits the following spectroscopic data?

IR: 1200 cm-1

1H NMR: 1.4 δ (singlet, 6H), 3.2 δ (singlet, 6H)

13C NMR: 28, 45, 100

An illustration shows the structure of five compounds. The first compound labeled 1 has a SMILES string of CC(C)(CO)OC. The second compound labeled 2 has a SMILES string of CC(C)(OC)OC. The third compound labeled 3 has a SMILES string of CCOCOC. The fourth compound labeled 4 has a SMILES string of CCC(C)(O)OC. The fifth compound labeled 5 has a SMILES string of COCCCOC.

A) I

B) II

C) III

D) IV

E) V

Diff: 3

Learning Objective: 15.9 Distinguish between compounds using 1H NMR spectroscopy

132) What is an appropriate structure for structure for a compound with molecular formula C6H10O that fits the following spectroscopic data?

IR: 3400 cm-1(broad), 3250 cm-1(sharp), 2150 cm-1

1H NMR: 1.0 δ (triplet, 3H), 1.5 δ (singlet, 3H), 1.6 δ (quartet, 2H), 2.0 δ (singlet, 1H), 2.5 δ (singlet, 1H)

13C NMR: 4.1, 26, 35, 67.6, 69.4

A) I

B) II

C) III

D) IV

E) V

Diff: 3

Learning Objective: 15.9 Distinguish between compounds using 1H NMR spectroscopy

133) What is an appropriate structure for a compound with molecular formula C8H15ClO3 that fits the following spectroscopic data?

IR: 1780 cm-1, 1150 cm-1

1H NMR: 1.1 δ (triplet, 6H), 1.9 δ (quartet, 2H), 2.8 δ (triplet, 2H), 3.4 δ (quartet, 4H), 4.2 δ (triplet, 1H)

13C NMR: 15, 31, 38, 57, 100, 173

A) I

B) II

C) III

D) IV

E) V

Diff: 3

Learning Objective: 15.9 Distinguish between compounds using 1H NMR spectroscopy

134) What is an appropriate structural formula for a compound with the molecular formula C3H6O2 that displays the following IR, 1H NMR and 13C NMR spectra?

A) I

B) II

C) III

D) IV

E) V

Diff: 2

Learning Objective: 15.9 Distinguish between compounds using 1H NMR spectroscopy

135) What is an appropriate structure for a compound with the molecular formula C6H12O that displays the following IR, 1H NMR and 13C NMR spectra?

An illustration shows the structure of five compounds. The first compound labeled 1 has a SMILES string of CCCCC(=O)C. The second compound labeled 2 has a SMILES string of CCCC(=O)CC. The third compound labeled 3 has a SMILES string of CCC/C=C/OC. The fourth compound labeled 4 has a SMILES string of CC(C)CCCO. The fifth compound labeled 5 has a SMILES string of CC(C)CC(=O)C.

A) I

B) II

C) III

D) IV

E) V

Diff: 2

Learning Objective: 15.9 Distinguish between compounds using 1H NMR spectroscopy

136) What is an appropriate structure for a compound with the molecular formula C6H4Cl2O that displays the following IR, 1H NMR and 13C NMR spectra?

$A graph shows the I R spectrum of a compound having a molecular formula, C 6 H 4 C l 2 O. The horizontal axis plots wavenumber in reciprocal centimeters and has a decreasing scale from left to right ranging from 4000 to 500 in increments of 1000. The vertical axis plots transmittance in percentage ranging from 0 to 100 in increments of 50. A curve starts at (4000, 100) to oscillate giving rise to multiple inverted peaks. The curve reaches some minimum points at (3437, 15), (3074, 87), (1705, 65), (1577, 40), (1466, 32), (1450, 20), (1338, 45), (1242, 35), (1176, 45), (771, 20), (714, 65), (548, 75); respectively, to end at (500, 100).$

A) I

B) II

C) III

D) IV

E) V

Diff: 2

Learning Objective: 15.9 Distinguish between compounds using 1H NMR spectroscopy

137) What is an appropriate structure for a compound with the molecular formula C10H14 that displays the following IR, 1H NMR, 13C NMR spectra?

SDBS

An illustration shows the structure of five compounds. The first compound labeled 1 has a SMILES string of CCC(C)c1ccccc1. The second compound labeled 2 has a SMILES string of CCc1c(cccc1C)C. The third compound labeled 3 has a SMILES string of CCCCc1ccccc1. The fourth compound labeled 4 has a SMILES string of CCc1ccc(cc1)CC. The fifth compound labeled 5 has a SMILES string of Cc1ccc(cc1)C(C)C.

A) I

B) II

C) III

D) IV

E) V

Diff: 2

Learning Objective: 15.9 Distinguish between compounds using 1H NMR spectroscopy

138) What is an appropriate structure for a compound with the molecular formula C8H11N that displays the following IR, 1H NMR, 13C NMR spectra?

SDBS

An illustration shows the structure of five compounds. The first compound labeled 1 has a SMILES string of CCc1ccc(cc1)N. The second compound labeled 2 has a SMILES string of CC(c1ccccc1)N. The third compound labeled 3 has a SMILES string of c1ccc(cc1)CN. The fourth compound labeled 4 has a SMILES string of Cc1ccc(cc1C)N. The fifth compound labeled 5 has a SMILES string of Cc1ccnc(c1)C.

A) I

B) II

C) III

D) IV

E) V

Diff: 2

Learning Objective: 15.9 Distinguish between compounds using 1H NMR spectroscopy

139) What is an appropriate structure for a compound with the molecular formula C8H14O3 that displays the following IR, 1H NMR, 13C NMR spectra?

SDBS

A) I

B) II

C) III

D) IV

E) V

Diff: 2

Learning Objective: 15.9 Distinguish between compounds using 1H NMR spectroscopy

140) What is an appropriate structure for a compound with molecular formula C7H14O2 that displays the following IR, 1H NMR, 13C NMR spectra?

SDBS

An illustration shows the structure of five compounds. The first compound labeled 1 has a SMILES string of CCCC(=O)OC(C)C. The second compound labeled 2 has a SMILES string of CCCCOCCC=O. The third compound labeled 3 has a SMILES string of CCCOC(=O)C(C)C. The fourth compound labeled 4 has a SMILES string of CCC(C)CC(=O)OC. The fifth compound labeled 5 has a SMILES string of CCCC(=O)OCCC.

A) I

B) II

C) III

D) IV

E) V

Diff: 3

Learning Objective: 15.9 Distinguish between compounds using 1H NMR spectroscopy

141) An unknown compound displays the following IR, 1H NMR, 13C NMR and mass spectra. What is a reasonable structure for this compound?

SDBS

An illustration shows the structure of five compounds. The first compound labeled 1 has a SMILES string of CCCNCCC. The second compound labeled 2 has a SMILES string of CCCCNCC. The third compound labeled 3 has a SMILES string of CCCCNCC. The fourth compound labeled 4 has a SMILES string of CCC(C)NCC. The fifth compound labeled 5 has a SMILES string of CC(C)NC(C)C.

A) I

B) II

C) III

D) IV

E) V

Diff: 3

Learning Objective: 15.9 Distinguish between compounds using 1H NMR spectroscopy

© (2021) John Wiley & Sons, Inc. All rights reserved. Instructors who are authorized users of this course are permitted to download these materials and use them in connection with the course. Except as permitted herein or by law, no part of these materials should be reproduced, stored in a retrieval system, or transmitted, in any form or by any means, electronic, mechanical, photocopying, recording or otherwise.

Document Information

Document Type:

DOCX

Chapter Number:

Created Date:

Aug 21, 2025

Chapter Name:

Chapter 15 Nuclear Magnetic Resonance Spectroscopy

Author:

David R. Klein

Connected Book

Organic Chemistry 4e | Test Bank by Klein

By David R. Klein

Test Bank General

View Product →

Explore recommendations drawn directly from what you're reading

Chapter 13 Ethers And Epoxides; Thiols And Sulfides

DOCX Ch. 13

Chapter 14 Infrared Spectroscopy And Mass Spectrometry

DOCX Ch. 14

Chapter 15 Nuclear Magnetic Resonance Spectroscopy

DOCX Ch. 15 Current

Chapter 16 Conjugated Pi Systems And Pericyclic Reactions

DOCX Ch. 16

Chapter 17 Aromatic Compounds

DOCX Ch. 17

$24.99

100% satisfaction guarantee

Buy Full Test Bank

Quick Navigation

Preview Document Info Connected Book Recommendations

Benefits

Immediately available after payment

Answers are available after payment

ZIP file includes all related files

Files are in Word format (DOCX)

Check the description to see the contents of each ZIP file

We do not share your information with any third party

Chapter 15 Nuclear Magnetic Resonance Spectroscopy Exam Prep

Document Information

Connected Book

Organic Chemistry 4e | Test Bank by Klein

Explore recommendations drawn directly from what you're reading

$24.99

Quick Navigation

Benefits

Report Unauthorized Use

Added to Cart