Question 1

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-pentene 
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-pentene D

Question 2

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) CH3O2CCO2CH2CH3 
A) HO2CC(CH3)2CO2H 
B) CH3O2CCH2CO2CH3 
C) HO2CCH2CH2CH2CO2H 
D) CH3O2CCH2CH2CO2H 
E) CH3O2CCO2CH2CH3 A

Question 3

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 E

Question 4

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 5

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

Question 6

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 7

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

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 = doublet 
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

Question 8

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

Accepted Answer

A) 0 
B) 1 
C) 2 
D) 3 
E) 10 
A) 0 
B) 1 
C) 2 
D) 3 
E) 10

Question 9

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

Question 10

________ 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 11

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 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

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 14

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

Question 15

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 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) ultraviolet 
A) X-ray 
B) infrared 
C) visible 
D) radio 
E) ultraviolet

Question 17

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 18

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 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

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

Exam 14: Nmr Spectroscopy

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

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)

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

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

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).

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)

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

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

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)

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

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

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.

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

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

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

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)

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

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,

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.

Remembering General Chemistry: Electronic Structure and Bonding

Acids and Bases: Central to Understanding Organic Chemistry

An Introduction to Organic Compounds: Nomenclature, physical Properties, and Structure

Isomers: the Arrangement of Atoms in Space

Alkenes: Structure,nomenclature,and an Introduction to Reactivity - Thermodynamics and Kinetics

The Reactions of Alkenes - the Stereochemistry of Addition Reactions

The Reactions of Alkynes - Introduction to Multistep Synthesis

Delocalized Electrons: Their Effect on Stability, pka, and the Products of a Reaction - Aromaticity and Electronic Effects: an Introduction to the Reactions of Benzene

Substitution and Elimination Reactions of Alkyl Halides

Reactions of Alcohols, ethers, epoxides, amines and Sulfur-Containing Compounds

Organometallic Compounds

Radicals

Mass Spectrometry,infrared Spectroscopy,and Uvvis Spectroscopy

Reactions of Carboxylic Acids and Carboxylic Acid Derivatives

Reactions of Aldehydes and Ketones

Reactions at the Α-Carbon

Reactions of Benzene and Substituted Benzenes

More About Amines - Reactions of Heterocylic Compounds

The Organic Chemistry of Carbohydrates

Amino Acids,peptides,and Proteins

Catalysis in Organic Reactions and in Enzymatic Reactions

The Organic Chemistry of the Coenzymes, compounds Derived From Vitamins

The Organic Chemistry of the Metabolic Pathways

The Organic Chemistry of Lipids

The Chemistry of the Nucleic Acids

Synthetic Polymers

Pericyclic Reactions

Filters

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

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)

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

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

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).

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)

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

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

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)

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

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

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

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

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)

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,

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.