Question 1

How many unique protons are present in each of the following compounds?

Accepted Answer

A)  I = 6; II = 3; III = 6. 
B)  I = 5; II = 4; III = 6. 
C)  I = 6; II = 4; III = 4. 
D)  I = 6; II = 4; III = 6. 
A)  I = 6; II = 3; III = 6. 
B)  I = 5; II = 4; III = 6. 
C)  I = 6; II = 4; III = 4. 
D)  I = 6; II = 4; III = 6. D

Question 2

Which compound does not give four sets of absorptions in its 1H NMR spectrum (i.e., which compound does not have four unique hydrogens)?

Accepted Answer

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

Question 3

How many different kinds of protons are present in each of the following compounds?

Accepted Answer

A)  I = 4; II = 4; III = 4. 
B)  I = 4; II = 4; III = 5. 
C)  I = 3; II = 3; III = 5. 
D)  I = 3; II = 4; III = 5. 
A)  I = 4; II = 4; III = 4. 
B)  I = 4; II = 4; III = 5. 
C)  I = 3; II = 3; III = 5. 
D)  I = 3; II = 4; III = 5. D

Question 4

How many different kinds of protons are present in each of the following compounds?

Accepted Answer

A)  a: 5; b: 6 
B)  a: 5; b: 5 
C)  a: 4; b: 6 
D)  a: 4; b: 5 
A)  a: 5; b: 6 
B)  a: 5; b: 5 
C)  a: 4; b: 6 
D)  a: 4; b: 5

Question 5

How many different kinds of protons are present in each of the following compounds?

Accepted Answer

A)  I = 2; II = 4; III = 6. 
B)  I = 2; II = 4; III = 4. 
C)  I = 3; II = 3; III = 5. 
D)  I = 2; II = 4; III = 5. 
A)  I = 2; II = 4; III = 6. 
B)  I = 2; II = 4; III = 4. 
C)  I = 3; II = 3; III = 5. 
D)  I = 2; II = 4; III = 5.

Question 6

How many peaks would be observed for each of the circled protons in the compounds below?

Accepted Answer

A)  I = 1; II = 4; III = 7. 
B)  I = 3; II = 3; III = 7. 
C)  I = 2; II = 4; III = 7. 
D)  I = 2; II = 4; III = 6. 
A)  I = 1; II = 4; III = 7. 
B)  I = 3; II = 3; III = 7. 
C)  I = 2; II = 4; III = 7. 
D)  I = 2; II = 4; III = 6.

Question 7

An unknown compound X has the molecular formula C10H11O2Br. Compound X shows a strong absorption in its IR spectrum at 1700 cm-1. The 1H NMR spectral data for compound X is given below. What is the structure of compound X?

Accepted Answer

A)  Only I 
B)  Only II 
C)  Only III 
D)  I or II 
A)  Only I 
B)  Only II 
C)  Only III 
D)  I or II

Question 8

Which of the following compounds does not show only one signal in its 1H NMR spectrum?

Accepted Answer

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

Question 9

How many peaks would be observed for each of the circled protons in the compounds below?

Accepted Answer

A)  I = 8; II = 4; III = 3; IV = 3. 
B)  I = 7; II = 4; III = 3; IV = 4. 
C)  I = 7; II = 3; III = 3; IV = 3. 
D)  I = 7; II = 4; III = 2; IV = 4. 
A)  I = 8; II = 4; III = 3; IV = 3. 
B)  I = 7; II = 4; III = 3; IV = 4. 
C)  I = 7; II = 3; III = 3; IV = 3. 
D)  I = 7; II = 4; III = 2; IV = 4.

Question 10

How many different kinds of protons are present in each of the following molecules?

Accepted Answer

A)  I = 6; II = 3; III = 4. 
B)  I = 5; II = 3; III = 4. 
C)  I = 6; II = 4; III = 5. 
D)  I = 6; II = 4; III = 4. 
A)  I = 6; II = 3; III = 4. 
B)  I = 5; II = 3; III = 4. 
C)  I = 6; II = 4; III = 5. 
D)  I = 6; II = 4; III = 4.

Question 11

Which of the indicated protons in the molecules below would absorb furthest downfield in a 1H NMR spectrum?

Accepted Answer

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

Question 12

How could spectroscopy be used to distinguish between the following compounds?

Accepted Answer

A)  Compound A has a triplet in its 1H NMR spectrum at 1.0 ppm. 
B)  Compound B has a peak at 3200-3500 cm-1 in its IR spectrum. 
C)  Compound A has a peak in its IR spectrum at 2900 cm-1. 
D)  Compound A has a triplet in its 1H NMR spectrum at 1.0 ppm and compound B has a peak at 3200-3500 cm-1 in its IR spectrum. 
A)  Compound A has a triplet in its 1H NMR spectrum at 1.0 ppm. 
B)  Compound B has a peak at 3200-3500 cm-1 in its IR spectrum. 
C)  Compound A has a peak in its IR spectrum at 2900 cm-1. 
D)  Compound A has a triplet in its 1H NMR spectrum at 1.0 ppm and compound B has a peak at 3200-3500 cm-1 in its IR spectrum.

Question 13

An unknown compound A has the molecular formula C7H14O2. Compound A absorbs strongly in the IR at 1700 cm-1. The 1H NMR spectral data for compound A are given below. What is the structure of compound A?

Accepted Answer

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

Question 14

What is the relationship between Ha and Hb in the following compound?

Accepted Answer

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

Question 15

What is the relationship between Ha and Hb in the following compound?

Accepted Answer

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

Question 16

How many different kinds of protons are present in each of the following compounds?

Accepted Answer

A)  I = 4; II = 3; III = 1. 
B)  I = 4; II = 4; III = 1. 
C)  I = 4; II = 4; III = 2. 
D)  I = 3; II = 3; III = 1. 
A)  I = 4; II = 3; III = 1. 
B)  I = 4; II = 4; III = 1. 
C)  I = 4; II = 4; III = 2. 
D)  I = 3; II = 3; III = 1.

Question 17

Which of the indicated protons would absorb furthest downfield in a 1H NMR spectrum?

Accepted Answer

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

Question 18

An unknown compound has the formula of C9H12. The following 1H NMR peaks were observed: Doublet at F1F1F1S1F1F1F10 1.22
Septet at F1F1F1S1F1F1F10 2.83
Multiplet at F1F1F1S1F1F1F10 7.09
From the data above, pick the compound below that fits the spectra data.

Accepted Answer

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

Question 19

Into how many peaks will the circled proton be split?

Accepted Answer

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

Question 20

An unknown compound X has the empirical formula C3H6O and a molecular ion in its mass spectrum at 116. Compound X shows no IR absorption at 3200-3600 cm-1 but shows a peak at 1700 cm-1. The 1H NMR spectral data of X is shown below. What is the structure of compound X?

Accepted Answer

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

Exam 14: Nuclear Magnetic Resonance Spectroscopy

How many unique protons are present in each of the following compounds?

Which compound does not give four sets of absorptions in its 1H NMR spectrum (i.e., which compound does not have four unique hydrogens)?

How many different kinds of protons are present in each of the following compounds?

How many different kinds of protons are present in each of the following compounds?

How many different kinds of protons are present in each of the following compounds?

How many peaks would be observed for each of the circled protons in the compounds below?

An unknown compound X has the molecular formula C10H11O2Br. Compound X shows a strong absorption in its IR spectrum at 1700 cm-1. The 1H NMR spectral data for compound X is given below. What is the structure of compound X?

Which of the following compounds does not show only one signal in its 1H NMR spectrum?

How many peaks would be observed for each of the circled protons in the compounds below?

How many different kinds of protons are present in each of the following molecules?

Which of the indicated protons in the molecules below would absorb furthest downfield in a 1H NMR spectrum?

How could spectroscopy be used to distinguish between the following compounds?

An unknown compound A has the molecular formula C7H14O2. Compound A absorbs strongly in the IR at 1700 cm-1. The 1H NMR spectral data for compound A are given below. What is the structure of compound A?

What is the relationship between Ha and Hb in the following compound?

What is the relationship between Ha and Hb in the following compound?

How many different kinds of protons are present in each of the following compounds?

Which of the indicated protons would absorb furthest downfield in a 1H NMR spectrum?

An unknown compound has the formula of C9H12. The following 1H NMR peaks were observed: Doublet at  1.22 Septet at  2.83 Multiplet at  7.09 From the data above, pick the compound below that fits the spectra data.

Into how many peaks will the circled proton be split?

An unknown compound X has the empirical formula C3H6O and a molecular ion in its mass spectrum at 116. Compound X shows no IR absorption at 3200-3600 cm-1 but shows a peak at 1700 cm-1. The 1H NMR spectral data of X is shown below. What is the structure of compound X?

Structure and Bonding

Acids and Bases

Introduction to Organic Molecules and Functional Groups

Alkanes

Stereochemistry

Understanding Organic Reactions

Alkyl Halides and Nucleophilic Substitution

Alkyl Halides and Elimination Reactions

Alcohols, Ethers and Epoxides

Alkenes

Alkynes

Oxidation and Reduction

Mass Spectrometry and Infrared Spectroscopy

Radical Reactions

Conjugation, Resonance, and Dienes

Benzene and Aromatic Compounds

Electrophilic Aromatic Substitution

Carboxylic Acids and the Acidity of the O-H Bond

Introduction to Carbonyl Chemistry; Organometallic Reagents; Oxidation and Reduction

Aldehydes and Ketones Nucleophilic Addition

Carboxylic Acids and Derivatives

Substitution Reactions of Carbonyl Compounds at the Alpha-Carbon

Carbonyl Condensation Reactions

Amines

Carbon-Carbon Bond Forming Reactions in Organic Synthesis

Pericyclic Reactions

Carbohydrates

Amino Acids and Proteins

Lipids

Synthetic Polymers

Filters

Which compound does not give four sets of absorptions in its ¹H NMR spectrum (i.e., which compound does not have four unique hydrogens)?

An unknown compound X has the molecular formula C₁₀H₁₁O₂Br. Compound X shows a strong absorption in its IR spectrum at 1700 cm^-1. The ¹H NMR spectral data for compound X is given below. What is the structure of compound X?

Which of the following compounds does not show only one signal in its ¹H NMR spectrum?

Which of the indicated protons in the molecules below would absorb furthest downfield in a ¹H NMR spectrum?

An unknown compound A has the molecular formula C₇H₁₄O₂. Compound A absorbs strongly in the IR at 1700 cm^-1. The ¹H NMR spectral data for compound A are given below. What is the structure of compound A?

What is the relationship between H_a and H_b in the following compound?

What is the relationship between H_a and H_b in the following compound?

Which of the indicated protons would absorb furthest downfield in a ¹H NMR spectrum?

An unknown compound has the formula of C₉H₁₂. The following ¹H NMR peaks were observed: Doublet at  1.22 Septet at  2.83 Multiplet at  7.09 From the data above, pick the compound below that fits the spectra data.

An unknown compound X has the empirical formula C₃H₆O and a molecular ion in its mass spectrum at 116. Compound X shows no IR absorption at 3200-3600 cm^-1 but shows a peak at 1700 cm^-1. The ¹H NMR spectral data of X is shown below. What is the structure of compound X?