Question 1

Deduce the identity of the compound from the data provided. C8H13Br: IR (cm-1) : 2950,2150
 1H NMR (δ,splitting,integral) : 3.5 (t,2H) ,1.8 (t,2H) ,
0) 9 (s,9H) 
 13C NMR: 6 signals

Accepted Answer

A)  CH3CHBrCCC(CH3) 3
B)  HCCCH2C(CH3) 2CH2CH2Br
C)  3-bromo-1,2-dimethylcyclohexene
D)  4-bromo-1,2,4-trimethylcyclopentene
E)  BrCH2CH2CCC(CH3) 3F) A) and D)
G) A) and E)

Question 2

The chair form of cyclohexane has protons in two distinct environments,axial and equatorial.When the proton NMR of cyclohexane is run on a 100 MHz instrument at 23°C,only one signal for the compound is observed.Explain this apparent contradiction.

Accepted Answer

Axial and equatorial positions are being...

Question 3

Give the structure of a compound that has a formula of C5H10O2, and has a triplet (3H,1.1 ppm) ,sextet (2H,1.8 ppm) ,triplet (2H,2.3 ppm) and a singlet (3H,3.8 ppm) in the 1H NMR spectrum.

Accepted Answer

A)   5H10O2, and has a triplet (3H,1.1 ppm) ,sextet (2H,1.8 ppm) ,triplet (2H,2.3 ppm) and a singlet (3H,3.8 ppm) in the 1H NMR spectrum. 
A)     
B)     
C)     
D)     
E)    " class="answers-bank-image d-inline" rel="preload" >
B)   5H10O2, and has a triplet (3H,1.1 ppm) ,sextet (2H,1.8 ppm) ,triplet (2H,2.3 ppm) and a singlet (3H,3.8 ppm) in the 1H NMR spectrum. 
A)     
B)     
C)     
D)     
E)    " class="answers-bank-image d-inline" rel="preload" >
C)   5H10O2, and has a triplet (3H,1.1 ppm) ,sextet (2H,1.8 ppm) ,triplet (2H,2.3 ppm) and a singlet (3H,3.8 ppm) in the 1H NMR spectrum. 
A)     
B)     
C)     
D)     
E)    " class="answers-bank-image d-inline" rel="preload" >
D)   5H10O2, and has a triplet (3H,1.1 ppm) ,sextet (2H,1.8 ppm) ,triplet (2H,2.3 ppm) and a singlet (3H,3.8 ppm) in the 1H NMR spectrum. 
A)     
B)     
C)     
D)     
E)    " class="answers-bank-image d-inline" rel="preload" >
E)   5H10O2, and has a triplet (3H,1.1 ppm) ,sextet (2H,1.8 ppm) ,triplet (2H,2.3 ppm) and a singlet (3H,3.8 ppm) in the 1H NMR spectrum. 
A)     
B)     
C)     
D)     
E)    " class="answers-bank-image d-inline" rel="preload" >F) B) and C)
G) A) and E)

Question 4

Provide the structure that is consistent with the data below.
C7H14O2
IR (cm-1): 2950,1750
1H NMR (d): 2.3 (2H,q),1.0 (3H,t),0.9 (9H,s)
13C NMR (d): 185 (s),78 (s),29 (t),14 (q),12 (q)

Accepted Answer

Question 5

What splitting pattern is observed in the proton NMR spectrum for the indicated hydrogens?

Accepted Answer

A)  singlet
B)  doublet
C)  triplet
D)  quartet
E)  septetF) C) and E)
G) A) and E)

Question 6

How many signals will be observable in the DEPT 13C NMR spectrum of naphthalene (shown below) ? 13C NMR spectrum of naphthalene (shown below) ?   A) 0 B) 1 C) 2 D) 3 E) 10" class="answers-bank-image d-inline" rel="preload" >

Accepted Answer

A)  0
B)  1
C)  2
D)  3
E)  10F) None of the above
G) B) and E)

Question 7

Deduce the structure from the data given: C8H10O; 13C NMR δ (coupling): 140 (s),128 (d),126 (d),122 (d),60 (t),15 (q).

Accepted Answer

Question 8

Give the structure of a compound that has a formula of C9H10O2 and has signals in the 13C NMR spectrum at 13.6 ppm (CH3) ; 59.1 ppm (CH2) ; 128.4 ppm (CH) ; 129.7 ppm (CH) ; 130.5 ppm (C) ; 132.8 ppm (CH) ; and 167.0 ppm (C) .

Accepted Answer

A)   9H10O2 and has signals in the 13C NMR spectrum at 13.6 ppm (CH3) ; 59.1 ppm (CH2) ; 128.4 ppm (CH) ; 129.7 ppm (CH) ; 130.5 ppm (
C)  ; 132.8 ppm (CH) ; and 167.0 ppm (
C)  . 
A)     
B)     
C)     
D)     
E)    " class="answers-bank-image d-inline" rel="preload" >
B)   9H10O2 and has signals in the 13C NMR spectrum at 13.6 ppm (CH3) ; 59.1 ppm (CH2) ; 128.4 ppm (CH) ; 129.7 ppm (CH) ; 130.5 ppm (
C)  ; 132.8 ppm (CH) ; and 167.0 ppm (
C)  . 
A)     
B)     
C)     
D)     
E)    " class="answers-bank-image d-inline" rel="preload" >
C)   9H10O2 and has signals in the 13C NMR spectrum at 13.6 ppm (CH3) ; 59.1 ppm (CH2) ; 128.4 ppm (CH) ; 129.7 ppm (CH) ; 130.5 ppm (
C)  ; 132.8 ppm (CH) ; and 167.0 ppm (
C)  . 
A)     
B)     
C)     
D)     
E)    " class="answers-bank-image d-inline" rel="preload" >
D)   9H10O2 and has signals in the 13C NMR spectrum at 13.6 ppm (CH3) ; 59.1 ppm (CH2) ; 128.4 ppm (CH) ; 129.7 ppm (CH) ; 130.5 ppm (
C)  ; 132.8 ppm (CH) ; and 167.0 ppm (
C)  . 
A)     
B)     
C)     
D)     
E)    " class="answers-bank-image d-inline" rel="preload" >
E)   9H10O2 and has signals in the 13C NMR spectrum at 13.6 ppm (CH3) ; 59.1 ppm (CH2) ; 128.4 ppm (CH) ; 129.7 ppm (CH) ; 130.5 ppm (
C)  ; 132.8 ppm (CH) ; and 167.0 ppm (
C)  . 
A)     
B)     
C)     
D)     
E)    " class="answers-bank-image d-inline" rel="preload" >F) A) and B)
G) A) and E)

Question 9

Deduce the identity of the compound from the data provided. C7H12: IR (cm-1) : 3300,2950,2220; 13C NMR: 5 signals

Accepted Answer

A)  1,2-dimethylcyclopentene
B)  5-methyl-2-hexyne
C)  3,3-dimethyl-1-pentyne
D)  4,4-dimethyl-1-pentyne
E)  2,4-dimethyl-2-penteneF) B) and C)
G) A) and C) D

Question 10

How many signals would you expect to see in the 1H NMR spectrum of the following compound? 1H NMR spectrum of the following compound?   A) 6 B) 5 C) 4 D) 3 E) 2" class="answers-bank-image d-inline" rel="preload" >

Accepted Answer

A)  6
B)  5
C)  4
D)  3
E)  2F) C) and D)
G) B) and E) E

Question 11

________ is commonly used as an internal reference in NMR spectroscopy; its signal is assigned δ=0 in 1H and 13C NMR spectroscopy.

Accepted Answer

Tetramethy...

Question 12

Why is carbon-hydrogen coupling not generally seen in 1H NMR spectra?

Accepted Answer

Most carbons are ¹²C.This nucleus has only...

Question 13

Deduce the identity of the compound from the data provided. C5H8O4: IR (cm-1) : 2800-3300 (broad) ,2950,1740
 13C NMR (δ,splitting) : 17.3 (q) ,44.3 (s) ,210.5 (s)

Accepted Answer

A)  HO2CC(CH3) 2CO2H
B)  CH3O2CCH2CO2CH3
C)  HO2CCH2CH2CH2CO2H
D)  CH3O2CCH2CH2CO2H
E)  CH3O2CCO2CH2CH3F) B) and C)
G) A) and E) A

Question 14

Deduce the identity of the following compound from the spectral data given.
C9H10O2: 13C NMR,δ 18.06 (quartet),45.40 (doublet),127.32 (doublet),127.55 (doublet),128.61 (doublet),139.70 (singlet),180.98 (singlet); IR,broad 3500-2800,1708 cm-1

Accepted Answer

Question 15

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,singlet)

Accepted Answer

Question 16

Which of the following electromagnetic wave types is used in nuclear magnetic resonance spectroscopy?

Accepted Answer

A)  X-ray
B)  infrared
C)  visible
D)  radio
E)  ultravioletF) B) and E)
G) A) and B)

Question 17

Give the splitting pattern for each proton in the 1H NMR spectrum. 1H NMR spectrum.   A) a = triplet; b = doublet; c = doublet; d = multiplet; e = triplet B) a = doublet; b = triplet; c = doublet; d = multiplet; e = doublet C) a = triplet; b = quartet; c = triplet; d = multiplet; e = triplet D) a = singlet; b = doublet; c = singlet; d = multiplet; e = singlet E) a = triplet; b = quartet; c= triplet; d = multiplet; e = doublet" class="answers-bank-image d-inline" rel="preload" >

Accepted Answer

A)  a = triplet; b = doublet; c = doublet; d = multiplet; e = triplet
B)  a = doublet; b = triplet; c = doublet; d = multiplet; e = doublet
C)  a = triplet; b = quartet; c = triplet; d = multiplet; e = triplet
D)  a = singlet; b = doublet; c = singlet; d = multiplet; e = singlet
E)  a = triplet; b = quartet; c= triplet; d = multiplet; e = doubletF) None of the above
G) B) and D)

Question 18

Which of the following protons gives an NMR signal with the lowest chemical shift value (farthest upfield) ? F-CH2CH2CH2CH2CH2-Br
1 2 3 4 5

Accepted Answer

A)  1
B)  2
C)  3
D)  4
E)  5F) A) and D)
G) A) and C)

Question 19

Deduce the identity of the following compound from the spectral data given.
C5H10O: 1H NMR,δ 1.2 (6H,doublet),2.1 (3H,singlet),2.8 (1H,septet); IR,2980,1710 cm-1; MS,m/z 71,

Accepted Answer

Question 20

Deduce the identity of the following compound from the 1H NMR spectral data given.
C8H18O : δ 0.89 (6H,doublet),1.87 (1H,multiplet),3.17 (2H,doublet)(ppm)

Accepted Answer

Exam 14: Nmr Spectroscopy

Deduce the identity of the compound from the data provided. C8H13Br: IR (cm-1) : 2950,2150 1H NMR (δ,splitting,integral) : 3.5 (t,2H) ,1.8 (t,2H) , 0) 9 (s,9H) 13C NMR: 6 signals

Correct AnswerverifiedShow Answer

The chair form of cyclohexane has protons in two distinct environments,axial and equatorial.When the proton NMR of cyclohexane is run on a 100 MHz instrument at 23°C,only one signal for the compound is observed.Explain this apparent contradiction.

Correct AnswerverifiedAxial and equatorial positions are being...View AnswerShow Answer

Give the structure of a compound that has a formula of C5H10O2, and has a triplet (3H,1.1 ppm) ,sextet (2H,1.8 ppm) ,triplet (2H,2.3 ppm) and a singlet (3H,3.8 ppm) in the 1H NMR spectrum.

Correct AnswerverifiedShow Answer

Provide the structure that is consistent with the data below. C7H14O2 IR (cm-1): 2950,1750 1H NMR (d): 2.3 (2H,q),1.0 (3H,t),0.9 (9H,s) 13C NMR (d): 185 (s),78 (s),29 (t),14 (q),12 (q)

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What splitting pattern is observed in the proton NMR spectrum for the indicated hydrogens?

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How many signals will be observable in the DEPT 13C NMR spectrum of naphthalene (shown below) ?

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Deduce the structure from the data given: C8H10O; 13C NMR δ (coupling): 140 (s),128 (d),126 (d),122 (d),60 (t),15 (q).

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Give the structure of a compound that has a formula of C9H10O2 and has signals in the 13C NMR spectrum at 13.6 ppm (CH3) ; 59.1 ppm (CH2) ; 128.4 ppm (CH) ; 129.7 ppm (CH) ; 130.5 ppm (C) ; 132.8 ppm (CH) ; and 167.0 ppm (C) .

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Deduce the identity of the compound from the data provided. C7H12: IR (cm-1) : 3300,2950,2220; 13C NMR: 5 signals

Correct AnswerverifiedD

How many signals would you expect to see in the 1H NMR spectrum of the following compound?

Correct AnswerverifiedE

________ is commonly used as an internal reference in NMR spectroscopy; its signal is assigned δ=0 in 1H and 13C NMR spectroscopy.

Correct AnswerverifiedTetramethy...View AnswerShow Answer

Why is carbon-hydrogen coupling not generally seen in 1H NMR spectra?

Correct AnswerverifiedMost carbons are 12C.This nucleus has only...View AnswerShow Answer

Deduce the identity of the compound from the data provided. C5H8O4: IR (cm-1) : 2800-3300 (broad) ,2950,1740 13C NMR (δ,splitting) : 17.3 (q) ,44.3 (s) ,210.5 (s)

Correct AnswerverifiedA

Deduce the identity of the following compound from the spectral data given. C9H10O2: 13C NMR,δ 18.06 (quartet),45.40 (doublet),127.32 (doublet),127.55 (doublet),128.61 (doublet),139.70 (singlet),180.98 (singlet); IR,broad 3500-2800,1708 cm-1

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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,singlet)

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Which of the following electromagnetic wave types is used in nuclear magnetic resonance spectroscopy?

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Give the splitting pattern for each proton in the 1H NMR spectrum.

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Which of the following protons gives an NMR signal with the lowest chemical shift value (farthest upfield) ? F-CH2CH2CH2CH2CH2-Br 1 2 3 4 5

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Deduce the identity of the following compound from the spectral data given. C5H10O: 1H NMR,δ 1.2 (6H,doublet),2.1 (3H,singlet),2.8 (1H,septet); IR,2980,1710 cm-1; MS,m/z 71,

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Deduce the identity of the following compound from the 1H NMR spectral data given. C8H18O : δ 0.89 (6H,doublet),1.87 (1H,multiplet),3.17 (2H,doublet)(ppm)

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Deduce the identity of the compound from the data provided. C₈H₁₃Br: IR (cm^-1) : 2950,2150 ¹H NMR (δ,splitting,integral) : 3.5 (t,2H) ,1.8 (t,2H) , 0) 9 (s,9H) ¹³C NMR: 6 signals

Correct Answer
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Correct Answer
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Axial and equatorial positions are being...
View Answer

Give the structure of a compound that has a formula of C₅H₁₀O_2, and has a triplet (3H,1.1 ppm) ,sextet (2H,1.8 ppm) ,triplet (2H,2.3 ppm) and a singlet (3H,3.8 ppm) in the ¹H NMR spectrum.

Correct Answer
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Provide the structure that is consistent with the data below. C₇H₁₄O₂ IR (cm^-1): 2950,1750 ¹H NMR (d): 2.3 (2H,q),1.0 (3H,t),0.9 (9H,s) ¹³C NMR (d): 185 (s),78 (s),29 (t),14 (q),12 (q)

Correct Answer
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Correct Answer
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How many signals will be observable in the DEPT ¹³C NMR spectrum of naphthalene (shown below) ?

Correct Answer
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Deduce the structure from the data given: C₈H₁₀O; ¹³C NMR δ (coupling): 140 (s),128 (d),126 (d),122 (d),60 (t),15 (q).

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Give the structure of a compound that has a formula of C₉H₁₀O₂ and has signals in the ¹³C NMR spectrum at 13.6 ppm (CH₃) ; 59.1 ppm (CH₂) ; 128.4 ppm (CH) ; 129.7 ppm (CH) ; 130.5 ppm (C) ; 132.8 ppm (CH) ; and 167.0 ppm (C) .

Correct Answer
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Deduce the identity of the compound from the data provided. C₇H₁₂: IR (cm^-1) : 3300,2950,2220; ¹³C NMR: 5 signals

Correct Answer
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D

How many signals would you expect to see in the ¹H NMR spectrum of the following compound?

Correct Answer
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E

________ is commonly used as an internal reference in NMR spectroscopy; its signal is assigned δ=0 in ¹H and ¹³C NMR spectroscopy.

Correct Answer
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Tetramethy...
View Answer

Why is carbon-hydrogen coupling not generally seen in ¹H NMR spectra?

Correct Answer
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Most carbons are ¹²C.This nucleus has only...
View Answer

Deduce the identity of the compound from the data provided. C₅H₈O₄: IR (cm^-1) : 2800-3300 (broad) ,2950,1740 ¹³C NMR (δ,splitting) : 17.3 (q) ,44.3 (s) ,210.5 (s)

Correct Answer
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A

Deduce the identity of the following compound from the spectral data given. C₉H₁₀O₂: ¹³C NMR,δ 18.06 (quartet),45.40 (doublet),127.32 (doublet),127.55 (doublet),128.61 (doublet),139.70 (singlet),180.98 (singlet); IR,broad 3500-2800,1708 cm^-¹

Correct Answer
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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,singlet)

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Correct Answer
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Give the splitting pattern for each proton in the ¹H NMR spectrum.

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Which of the following protons gives an NMR signal with the lowest chemical shift value (farthest upfield) ? F-CH₂CH₂CH₂CH₂CH₂-Br 1 2 3 4 5

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Deduce the identity of the following compound from the spectral data given. C₅H₁₀O: ¹H NMR,δ 1.2 (6H,doublet),2.1 (3H,singlet),2.8 (1H,septet); IR,2980,1710 cm^-1; MS,m/z 71,

Correct Answer
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Deduce the identity of the following compound from the ¹H NMR spectral data given. C₈H₁₈O : δ 0.89 (6H,doublet),1.87 (1H,multiplet),3.17 (2H,doublet)(ppm)

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