Question 1

Draw a splitting tree to show the complex splitting pattern for the Hb proton. (Jcis = 10 Hz, trans = 15 Hz and Jgem = 2 Hz

Accepted Answer

Question 2

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 3

Provide a structure that is consistent with the data below.
C6H10
IR (cm-1): 2950, 2230
1H NMR ( d): 2.0 (1H, septet), 1.8 (3H, s), 0.9 (6H, d)
13C NMR (d ): 78 (s), 72 (s), 45 (d), 18 (q), 15 (q)

Accepted Answer

Question 4

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

Accepted Answer

Question 5

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 6

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

Accepted Answer

Question 7

Deduce the identity of the following compound from the 13C NMR data given.
C4H8O: δ 11.97 (triplet), 33.54 (triplet), 67.03 (doublet) (ppm)

Accepted Answer

Question 8

Draw the 1H NMR spectrum for the following compound.

Accepted Answer

Question 9

Which carbon signal shows up in the 0-50 ppm region of the proton spin decoupled 13C NMR spectrum?

Accepted Answer

A)  A 
B)  B 
C)  C 
D)  D 
E)  both C and D 
A)  A 
B)  B 
C)  C 
D)  D 
E)  both C and D

Question 10

Deduce the identity of the following compound from the NMR data given.
C4H6O2: 1H NMR, δ 2.28 (2H, multiplet), 2.50 (2H, triplet), 4.35 (2H, triplet);
13C NMR, δ 177.81 (singlet), 68.58 (triplet), 27.70 (triplet), 22.17 (triplet) (ppm)

Accepted Answer

Question 11

Using the scale below, draw the 1H NMR spectrum for isobutyl acetate, shown below. Present the peaks with correct splitting patterns and at the approximate chemical shift (+/- 0.5 ppm). Just above each peak, indicate the relative integration value of each type of hydrogen.

Accepted Answer

δ 3.9 ppm (d, 2H), 2

Question 12

Calculate the magnetic field that corresponds to the proton resonance frequency of 300.00 MHz. The gyromagnetic ratio of the 1H nucleus is

Accepted Answer

Question 13

Deduce the identity of the following compound from the 1H NMR data given.
C8H10O: δ 3.4 (3H, singlet), 4.5 (2H, singlet), 7.2 (5H, apparent singlet) (ppm)

Accepted Answer

Question 14

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 15

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

Accepted Answer

Question 16

Draw the 13C NMR spectrum for the following compound.

Accepted Answer

Question 17

Which of the structures shown below is consistent with the C-13 NMR (off resonance splitting for each peak is shown as a table within the figure) and H-NMR spectra? (formula = C9H11OBr)

Accepted Answer

A)    
B)    
C)    
D)    
E)    
A)    
B)    
C)    
D)    
E)

Question 18

Deduce the identity of the following compound from the 1H NMR data given.
C9H10O2: δ 2.2 (3H, singlet), 5.0 (2H, singlet), 7.2 (5H, singlet) (ppm)

Accepted Answer

Question 19

The protons marked Ha and Hb in the molecule below are ________.

Accepted Answer

A)  chemically equivalent 
B)  enantiotopic 
C)  diastereotopic 
D)  endotopic 
E)  none of the above 
A)  chemically equivalent 
B)  enantiotopic 
C)  diastereotopic 
D)  endotopic 
E)  none of the above

Question 20

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

Accepted Answer

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

Exam 13: Nuclear Magnetic Resonance Spectroscopy

Draw a splitting tree to show the complex splitting pattern for the Hb proton. (Jcis = 10 Hz, trans = 15 Hz and Jgem = 2 Hz

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)

Provide a structure that is consistent with the data below. C6H10 IR (cm-1): 2950, 2230 1H NMR ( d): 2.0 (1H, septet), 1.8 (3H, s), 0.9 (6H, d) 13C NMR (d ): 78 (s), 72 (s), 45 (d), 18 (q), 15 (q)

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

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

Deduce the identity of the following compound from the 13C NMR data given. C4H8O: δ 11.97 (triplet), 33.54 (triplet), 67.03 (doublet) (ppm)

Draw the 1H NMR spectrum for the following compound.

Which carbon signal shows up in the 0-50 ppm region of the proton spin decoupled 13C NMR spectrum?

Deduce the identity of the following compound from the NMR data given. C4H6O2: 1H NMR, δ 2.28 (2H, multiplet), 2.50 (2H, triplet), 4.35 (2H, triplet); 13C NMR, δ 177.81 (singlet), 68.58 (triplet), 27.70 (triplet), 22.17 (triplet) (ppm)

Using the scale below, draw the 1H NMR spectrum for isobutyl acetate, shown below. Present the peaks with correct splitting patterns and at the approximate chemical shift (+/- 0.5 ppm). Just above each peak, indicate the relative integration value of each type of hydrogen.

Calculate the magnetic field that corresponds to the proton resonance frequency of 300.00 MHz. The gyromagnetic ratio of the 1H nucleus is

Deduce the identity of the following compound from the 1H NMR data given. C8H10O: δ 3.4 (3H, singlet), 4.5 (2H, singlet), 7.2 (5H, apparent singlet) (ppm)

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

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

Draw the 13C NMR spectrum for the following compound.

Which of the structures shown below is consistent with the C-13 NMR (off resonance splitting for each peak is shown as a table within the figure) and H-NMR spectra? (formula = C9H11OBr)

Deduce the identity of the following compound from the 1H NMR data given. C9H10O2: δ 2.2 (3H, singlet), 5.0 (2H, singlet), 7.2 (5H, singlet) (ppm)

The protons marked Ha and Hb in the molecule below are ________.

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

Structure and Bonding

Acids and Bases; Functional Groups

Structure and Stereochemistry of Alkanes

The Study of Chemical Reactions

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Alkyl Halides; Nucleophilic Substitution

Structure and Synthesis of Alkenes; Elimination

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Reactions of Alcohols

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Draw a splitting tree to show the complex splitting pattern for the H_b proton. (J_cis = 10 Hz, trans = 15 Hz and J_gem = 2 Hz

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)

Provide a structure that is consistent with the data below. C₆H₁₀ IR (cm^-1): 2950, 2230 ¹H NMR ( d): 2.0 (1H, septet), 1.8 (3H, s), 0.9 (6H, d) ¹³C NMR (d ): 78 (s), 72 (s), 45 (d), 18 (q), 15 (q)

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

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

Deduce the identity of the following compound from the ¹³C NMR data given. C₄H₈O: δ 11.97 (triplet), 33.54 (triplet), 67.03 (doublet) (ppm)

Draw the ¹H NMR spectrum for the following compound.

Which carbon signal shows up in the 0-50 ppm region of the proton spin decoupled ¹³C NMR spectrum?

Deduce the identity of the following compound from the NMR data given. C₄H₆O₂: ¹H NMR, δ 2.28 (2H, multiplet), 2.50 (2H, triplet), 4.35 (2H, triplet); ¹³C NMR, δ 177.81 (singlet), 68.58 (triplet), 27.70 (triplet), 22.17 (triplet) (ppm)

Using the scale below, draw the ¹H NMR spectrum for isobutyl acetate, shown below. Present the peaks with correct splitting patterns and at the approximate chemical shift (+/- 0.5 ppm). Just above each peak, indicate the relative integration value of each type of hydrogen.

Calculate the magnetic field that corresponds to the proton resonance frequency of 300.00 MHz. The gyromagnetic ratio of the ¹H nucleus is

Deduce the identity of the following compound from the ¹H NMR data given. C₈H₁₀O: δ 3.4 (3H, singlet), 4.5 (2H, singlet), 7.2 (5H, apparent singlet) (ppm)

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

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

Draw the ¹³C NMR spectrum for the following compound.

Which of the structures shown below is consistent with the C-13 NMR (off resonance splitting for each peak is shown as a table within the figure) and H-NMR spectra? (formula = C₉H₁₁OBr)

Deduce the identity of the following compound from the ¹H NMR data given. C₉H₁₀O₂: δ 2.2 (3H, singlet), 5.0 (2H, singlet), 7.2 (5H, singlet) (ppm)

The protons marked H_a and H_b in the molecule below are ________.

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