Question 1

Determine the number of signals for isopentylamine in the 1H NMR spectrum.

Accepted Answer

A) 2 
B) 3 
C) 4 
D) 5 
E) 6 
A) 2 
B) 3 
C) 4 
D) 5 
E) 6

Question 2

How might the proton spectrum of ultrapure dimethylamine, (CH3)2NH, differ from the spectrum of this compound to which D2O has been added?

Accepted Answer

N-H signal will broa

Question 3

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

Question 4

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

Accepted Answer

A) 1 
B) 2 
C) 4 
D) 3 
E) 6 
A) 1 
B) 2 
C) 4 
D) 3 
E) 6

Question 5

Deduce the identity of the compound from the data provided.
C5H10O2: IR (cm-1): 2950, 1740; 13C NMR (δ, splitting): 15.8 (q), 19.7 (q), 68.4 (d), 195.3 (s)

Accepted Answer

Question 6

Using a 60 MHz spectrometer, the protons in dichloromethane appear at 5.30 ppm. When the same sample is placed in a 100 MHz instrument, where does the signal appear?

Accepted Answer

A) 8)33 ppm 
B) 3)18 ppm 
C) 5)30 ppm 
D) cannot be determined from information given 
A) 8)33 ppm 
B) 3)18 ppm 
C) 5)30 ppm 
D) cannot be determined from information given

Question 7

An unknown compound, C4H10O, gave the following proton NMR data:
Triplet at 1.13 ppm
Quartet at 3.38 ppm
What is the structure of the compound?

Accepted Answer

Question 8

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) septet 
A) singlet 
B) doublet 
C) triplet 
D) quartet 
E) septet

Question 9

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

Accepted Answer

A) 6 
B) 5 
C) 4 
D) 3 
E) 2 
A) 6 
B) 5 
C) 4 
D) 3 
E) 2

Question 10

Which of the following spectroscopic techniques uses the lowest energy of the electromagnetic radiation spectrum?

Accepted Answer

A) UV 
B) visible 
C) IR 
D) X-ray 
E) NMR 
A) UV 
B) visible 
C) IR 
D) X-ray 
E) NMR

Question 11

1H nuclei located near electronegative atoms tend to be ________ relative to 1H nuclei which are not.

Accepted Answer

A) shielded 
B) deshielded 
C) resonanced 
D) split 
E) none of the above 
A) shielded 
B) deshielded 
C) resonanced 
D) split 
E) none of the above

Question 12

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

Accepted Answer

Most carbons are ¹²C. This nucleus has onl

Question 13

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

Accepted Answer

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

Question 14

Which of the compounds below most closely matches the following 1H NMR data:
7.6 (2H, d), 7.3 (2H, d), 3.5 (3H, s), 2.2 (3H, s)?

Accepted Answer

Question 15

How might the two trimethylcyclohexane isomers shown below be most readily distinguished using NMR?

Accepted Answer

Number of

Question 16

Describe the difference between a ketone and an aldehyde in the 1H NMR spectrum.

Accepted Answer

A) An aldehyde has a signal at 9.0 - 10.0 ppm 
B) An aldehyde has a signal at 2.1 ppm. 
C) An aldehyde has a signal at 5.0 ppm/ 
D) An aldehyde has a signal at 3.5 ppm. 
E) An aldehyde has a signal at 8.0 ppm. 
A) An aldehyde has a signal at 9.0 - 10.0 ppm 
B) An aldehyde has a signal at 2.1 ppm. 
C) An aldehyde has a signal at 5.0 ppm/ 
D) An aldehyde has a signal at 3.5 ppm. 
E) An aldehyde has a signal at 8.0 ppm.

Question 17

Give the structure of a compound that has a formula of C6H12O and has a triplet (3H, 1.1 ppm), doublet (6H, 1.2 ppm), quartet (2H, 2.4 ppm), and septet (1H, 2.7 ppm)in the 1H NMR spectrum.

Accepted Answer

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

Question 18

Predict the number of signals in the 13C NMR spectrum for the following structure.

Accepted Answer

A) 5 
B) 6 
C) 7 
D) 8 
E) 9 
A) 5 
B) 6 
C) 7 
D) 8 
E) 9

Question 19

Deduce the identity of the following compound from the 1H NMR spectral data given.
C6H8O4 : δ 3.9 (6H, singlet), 6.1 (2H, singlet)(ppm)

Accepted Answer

Question 20

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

Accepted Answer

A) 7 
B) 3 
C) 4 
D) 2 
E) 8 
A) 7 
B) 3 
C) 4 
D) 2 
E) 8

Exam 15: Nmr Spectroscopy

Determine the number of signals for isopentylamine in the 1H NMR spectrum.

How might the proton spectrum of ultrapure dimethylamine, (CH3)2NH, differ from the spectrum of this compound to which D2O has been added?

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

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

Deduce the identity of the compound from the data provided. C5H10O2: IR (cm-1): 2950, 1740; 13C NMR (δ, splitting): 15.8 (q), 19.7 (q), 68.4 (d), 195.3 (s)

Using a 60 MHz spectrometer, the protons in dichloromethane appear at 5.30 ppm. When the same sample is placed in a 100 MHz instrument, where does the signal appear?

An unknown compound, C4H10O, gave the following proton NMR data: Triplet at 1.13 ppm Quartet at 3.38 ppm What is the structure of the compound?

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

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

Which of the following spectroscopic techniques uses the lowest energy of the electromagnetic radiation spectrum?

1H nuclei located near electronegative atoms tend to be ________ relative to 1H nuclei which are not.

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

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

Which of the compounds below most closely matches the following 1H NMR data: 7.6 (2H, d), 7.3 (2H, d), 3.5 (3H, s), 2.2 (3H, s)?

How might the two trimethylcyclohexane isomers shown below be most readily distinguished using NMR?

Describe the difference between a ketone and an aldehyde in the 1H NMR spectrum.

Give the structure of a compound that has a formula of C6H12O and has a triplet (3H, 1.1 ppm), doublet (6H, 1.2 ppm), quartet (2H, 2.4 ppm), and septet (1H, 2.7 ppm)in the 1H NMR spectrum.

Predict the number of signals in the 13C NMR spectrum for the following structure.

Deduce the identity of the following compound from the 1H NMR spectral data given. C6H8O4 : δ 3.9 (6H, singlet), 6.1 (2H, singlet)(ppm)

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

Remembering General Chemistry: Electronic Structure and Bonding

Acids and Bases: Central to Understanding Organic Chemistry

An Introduction to Organic Compounds

Isomers: the Arrangement of Atoms in Space

Alkenes Thermodynamics and Kinetics

Reactions of Alkenes

Reactions of Alkynes Introduction to Multistep Synthesis

Electron Delocalization, Resonance, and Aromaticity More About Molecular Orbital Theory

Substitution Reactions of Alkyl Halides

Elimination Reactions of Alkyl Halides Competition Between Substitution and Elimination

Reactions of Alcohols, Ethers, Epoxides, and Sulfur-Containing Compounds

Organometallic Compounds

Reactions of Alkanes, Radicals

Mass Spectrometry, Infrared Spectroscopy, and Uvvis Spectroscopy

Reactions of Carboxylic Acids and Carboxylic Acid Derivatives

Reactions of Aldehydes and Ketones

Reactions at the Alpha Carbon of Carbonyl Compounds

Reactions of Benzene and Substituted Benzenes

More About Amines Heterocylic Compounds

Carbohydrates

Amino Acids, Peptides, and Proteins

Catalysis

The Organic Mechanisms of the Coenzymes

The Chemistry of Metabolism

Nucleosides, Nucleotides, and Nucleic Acids

Synthetic Polymers

Pericyclic Reactions

Filters

Determine the number of signals for isopentylamine in the ¹H NMR spectrum.

How might the proton spectrum of ultrapure dimethylamine, (CH₃)₂NH, differ from the spectrum of this compound to which D₂O has been added?

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

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

Deduce the identity of the compound from the data provided. C₅H₁₀O₂: IR (cm^-1): 2950, 1740; ¹³C NMR (δ, splitting): 15.8 (q), 19.7 (q), 68.4 (d), 195.3 (s)

An unknown compound, C₄H₁₀O, gave the following proton NMR data: Triplet at 1.13 ppm Quartet at 3.38 ppm What is the structure of the compound?

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

¹H nuclei located near electronegative atoms tend to be ________ relative to ¹H nuclei which are not.

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

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

Which of the compounds below most closely matches the following ¹H NMR data: 7.6 (2H, d), 7.3 (2H, d), 3.5 (3H, s), 2.2 (3H, s)?

Describe the difference between a ketone and an aldehyde in the ¹H NMR spectrum.

Give the structure of a compound that has a formula of C₆H₁₂O and has a triplet (3H, 1.1 ppm), doublet (6H, 1.2 ppm), quartet (2H, 2.4 ppm), and septet (1H, 2.7 ppm)in the ¹H NMR spectrum.

Predict the number of signals in the ¹³C NMR spectrum for the following structure.

Deduce the identity of the following compound from the ¹H NMR spectral data given. C₆H₈O₄ : δ 3.9 (6H, singlet), 6.1 (2H, singlet)(ppm)

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