Question 1

What 1H NMR spectral data is expected for the compound shown?

Accepted Answer

A)  3.8 (1H, septet), 2.1 (3H, s), 1.0 (6H, d) 
B)  3.8 (1H, septet), 3.3 (3H, s), 1.0 (6H, d) 
C)  3.3 (3H, s), 2.6 (3H, septet), 1.0 (6H, d) 
D)  2.6 (1H, septet), 2.1 (3H, s), 1.0 (6H, d) 
A)  3.8 (1H, septet), 2.1 (3H, s), 1.0 (6H, d) 
B)  3.8 (1H, septet), 3.3 (3H, s), 1.0 (6H, d) 
C)  3.3 (3H, s), 2.6 (3H, septet), 1.0 (6H, d) 
D)  2.6 (1H, septet), 2.1 (3H, s), 1.0 (6H, d)

Question 2

Predict the number of signals expected (disregarding splitting) in the 1H spectrum of o-chlorophenol (2-chlorophenol).

Accepted Answer

Question 3

Provide a structure that is consistent with the data below.
C9H7Cl
IR (cm-1): 3050, 2950, 2220, 1620
1H NMR ( d): 7.8 (2H, d), 7.2 (2H, d), 2.1 (3H, s)
13C NMR (d ): 140 (s), 132, (s), 125 (d), 122 (d), 88 (s), 83 (s), 18 (q)

Accepted Answer

Question 4

Deduce the identity of the compound whose molecular formula is C8H14 from the spectral data provided: IR (cm-1): 2950, 2180; 1H NMR (δ): 0.9 (3H, t), 1.0 (9H, s), 2.3 (2H, q) (ppm).

Accepted Answer

2,2-dimeth

Question 5

How many peaks appear in the proton spin decoupled 13C NMR spectrum of the compound below?

Accepted Answer

Question 6

How many peaks appear in the proton spin decoupled 13C NMR spectrum of the compound below?

Accepted Answer

Question 7

If a molecule contains 4 elements of unsaturation and signals in the 1H NMR spectrum between δ 7.0 and 8.0 ppm, what structural group is likely to be present?

Accepted Answer

A)  a carbonyl group 
B)  an aromatic ring 
C)  a hydroxyl group 
D)  a cyclohexyl ring 
E)  a carbon-carbon triple bond 
A)  a carbonyl group 
B)  an aromatic ring 
C)  a hydroxyl group 
D)  a cyclohexyl ring 
E)  a carbon-carbon triple bond

Question 8

What 1H NMR spectral data is expected for the compound shown?

Accepted Answer

A)  3.8 (1H, septet), 2.1 (3H, s), 1.0 (6H, d) 
B)  3.8 (1H, septet), 3.3 (3H, s), 1.0 (6H, d) 
C)  3.3 (3H, s), 2.6 (3H, septet), 1.0 (6H, d) 
D)  2.6 (1H, septet), 2.1 (3H, s), 1.0 (6H, d) 
A)  3.8 (1H, septet), 2.1 (3H, s), 1.0 (6H, d) 
B)  3.8 (1H, septet), 3.3 (3H, s), 1.0 (6H, d) 
C)  3.3 (3H, s), 2.6 (3H, septet), 1.0 (6H, d) 
D)  2.6 (1H, septet), 2.1 (3H, s), 1.0 (6H, d)

Question 9

Deduce the identity of the following compound from the 13C NMR data given.
C6H12O: δ 29.80 (quartet), 30.82 (singlet), 56.53 (triplet), 203.36 (doublet) (ppm)

Accepted Answer

Question 10

Predict the number of signals expected in the proton spin decoupled 13C NMR spectrum of the compound shown below.

Accepted Answer

Question 11

Predict the number of signals expected in the proton spin decoupled 13C spectrum of p-dibromobenzene (1,4-dibromobenzene).

Accepted Answer

Question 12

Deduce the identity of the following compound from the 1H NMR data given.
C5H10O: δ 1.1 (6H, doublet), 2.2 (3H, singlet), 2.5 (1H, septet) (ppm)

Accepted Answer

Question 13

Deduce the identity of the following compound from the 13C NMR data given.
C8H8O: δ 26.4 (quartet), 128.0 (doublet), 128.3 (doublet), 133.0 (doublet), 137.0 (singlet), 198.0 (singlet) (ppm)

Accepted Answer

acetopheno

Question 14

Predict the number of signals expected in the proton spin decoupled 13C spectrum of 3-pentanone,

Accepted Answer

Question 15

Deduce the identity of the following compound from the 13C NMR data given.
C4H7Br: δ 18.0 (quartet), 33.0 (triplet), 128.0 (doublet), 131.0 (doublet) (ppm)

Accepted Answer

Question 16

Predict the number of distinct quartets expected in the off-resonance decoupled 13C NMR spectrum of the compound shown below.

Accepted Answer

Question 17

Use the structure below to state the relationship between the indicated protons as equivalent, enantiotopic, diastereotopic, or unrelated.   Ha & Hb:
Ha & Hc:
Hb & Hc:

Accepted Answer

H_a & H_b: Diastereotopi

Question 18

What is the relative area of each peak in a quartet spin-spin splitting pattern?

Accepted Answer

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

Question 19

Label the different 1H environments in the structure below a, b, c.... Then complete the table for each different type of proton. The first one is done for you as an example. (Note: there may be fewer than 7 different proton environments)   environments a b c d e f g
chemical shift
(+/- 0.5 ppm) 1.9
spin-spin splitting s

Accepted Answer

@#IMG-DLM& environments a b c d e f g
ch

Question 20

Deduce the identity of the following compound from the 1H NMR data given.
C3H3Cl5: δ 4.5 (1H, triplet), 6.1 (2H, doublet) (ppm)

Accepted Answer

Exam 13: Nuclear Magnetic Resonance Spectroscopy

What 1H NMR spectral data is expected for the compound shown?

Predict the number of signals expected (disregarding splitting) in the 1H spectrum of o-chlorophenol (2-chlorophenol).

Provide a structure that is consistent with the data below. C9H7Cl IR (cm-1): 3050, 2950, 2220, 1620 1H NMR ( d): 7.8 (2H, d), 7.2 (2H, d), 2.1 (3H, s) 13C NMR (d ): 140 (s), 132, (s), 125 (d), 122 (d), 88 (s), 83 (s), 18 (q)

Deduce the identity of the compound whose molecular formula is C8H14 from the spectral data provided: IR (cm-1): 2950, 2180; 1H NMR (δ): 0.9 (3H, t), 1.0 (9H, s), 2.3 (2H, q) (ppm).

How many peaks appear in the proton spin decoupled 13C NMR spectrum of the compound below?

How many peaks appear in the proton spin decoupled 13C NMR spectrum of the compound below?

If a molecule contains 4 elements of unsaturation and signals in the 1H NMR spectrum between δ 7.0 and 8.0 ppm, what structural group is likely to be present?

What 1H NMR spectral data is expected for the compound shown?

Deduce the identity of the following compound from the 13C NMR data given. C6H12O: δ 29.80 (quartet), 30.82 (singlet), 56.53 (triplet), 203.36 (doublet) (ppm)

Predict the number of signals expected in the proton spin decoupled 13C NMR spectrum of the compound shown below.

Predict the number of signals expected in the proton spin decoupled 13C spectrum of p-dibromobenzene (1,4-dibromobenzene).

Deduce the identity of the following compound from the 1H NMR data given. C5H10O: δ 1.1 (6H, doublet), 2.2 (3H, singlet), 2.5 (1H, septet) (ppm)

Deduce the identity of the following compound from the 13C NMR data given. C8H8O: δ 26.4 (quartet), 128.0 (doublet), 128.3 (doublet), 133.0 (doublet), 137.0 (singlet), 198.0 (singlet) (ppm)

Predict the number of signals expected in the proton spin decoupled 13C spectrum of 3-pentanone,

Deduce the identity of the following compound from the 13C NMR data given. C4H7Br: δ 18.0 (quartet), 33.0 (triplet), 128.0 (doublet), 131.0 (doublet) (ppm)

Predict the number of distinct quartets expected in the off-resonance decoupled 13C NMR spectrum of the compound shown below.

Use the structure below to state the relationship between the indicated protons as equivalent, enantiotopic, diastereotopic, or unrelated. Ha & Hb: Ha & Hc: Hb & Hc:

What is the relative area of each peak in a quartet spin-spin splitting pattern?

Deduce the identity of the following compound from the 1H NMR data given. C3H3Cl5: δ 4.5 (1H, triplet), 6.1 (2H, doublet) (ppm)

Introduction and Review

Structure and Properties of Organic Molecules

Structure and Stereochemistry of Alkanes

The Study of Chemical Reactions

Stereochemistry

Alkyl Halides: Nucleophilic Substitution and Elimination

Structure and Synthesis of Alkenes

Reactions of Alkenes

Alkynes

Structure and Synthesis of Alcohols

Reactions of Alcohols

Infrared Spectroscopy and Mass Spectrometry

Ethers, Epoxides, and Thioethers

Conjugated Systems, Orbital Symmetry, and Ultraviolet Spectroscopy

Aromatic Compounds

Reactions of Aromatic Compounds

Ketones and Aldehydes

Amines

Carboxylic Acids

Carboxylic Acid Derivatives

Condensations and Alpha Substitutions of Carboxyl Compounds

Carbohydrates and Nucleic Acids

Amino Acids, Peptides, and Proteins

Lipids

Synthetic Polymers

Filters

What ¹H NMR spectral data is expected for the compound shown?

Predict the number of signals expected (disregarding splitting) in the ¹H spectrum of o-chlorophenol (2-chlorophenol).

Provide a structure that is consistent with the data below. C₉H₇Cl IR (cm^-1): 3050, 2950, 2220, 1620 ¹H NMR ( d): 7.8 (2H, d), 7.2 (2H, d), 2.1 (3H, s) ¹³C NMR (d ): 140 (s), 132, (s), 125 (d), 122 (d), 88 (s), 83 (s), 18 (q)

Deduce the identity of the compound whose molecular formula is C₈H₁₄ from the spectral data provided: IR (cm^-1): 2950, 2180; ¹H NMR (δ): 0.9 (3H, t), 1.0 (9H, s), 2.3 (2H, q) (ppm).

How many peaks appear in the proton spin decoupled ¹³C NMR spectrum of the compound below?

How many peaks appear in the proton spin decoupled ¹³C NMR spectrum of the compound below?

If a molecule contains 4 elements of unsaturation and signals in the ¹H NMR spectrum between δ 7.0 and 8.0 ppm, what structural group is likely to be present?

What ¹H NMR spectral data is expected for the compound shown?

Deduce the identity of the following compound from the ¹³C NMR data given. C₆H₁₂O: δ 29.80 (quartet), 30.82 (singlet), 56.53 (triplet), 203.36 (doublet) (ppm)

Predict the number of signals expected in the proton spin decoupled ¹³C NMR spectrum of the compound shown below.

Predict the number of signals expected in the proton spin decoupled ¹³C spectrum of p-dibromobenzene (1,4-dibromobenzene).

Deduce the identity of the following compound from the ¹H NMR data given. C₅H₁₀O: δ 1.1 (6H, doublet), 2.2 (3H, singlet), 2.5 (1H, septet) (ppm)

Deduce the identity of the following compound from the ¹³C NMR data given. C₈H₈O: δ 26.4 (quartet), 128.0 (doublet), 128.3 (doublet), 133.0 (doublet), 137.0 (singlet), 198.0 (singlet) (ppm)

Predict the number of signals expected in the proton spin decoupled ¹³C spectrum of 3-pentanone,

Deduce the identity of the following compound from the ¹³C NMR data given. C₄H₇Br: δ 18.0 (quartet), 33.0 (triplet), 128.0 (doublet), 131.0 (doublet) (ppm)

Predict the number of distinct quartets expected in the off-resonance decoupled ¹³C NMR spectrum of the compound shown below.

Use the structure below to state the relationship between the indicated protons as equivalent, enantiotopic, diastereotopic, or unrelated. H_a & H_b: H_a & H_c: H_b & H_c:

Deduce the identity of the following compound from the ¹H NMR data given. C₃H₃Cl₅: δ 4.5 (1H, triplet), 6.1 (2H, doublet) (ppm)