Question 1

What orbitals are used to form the bond indicated in the following molecule?

Accepted Answer

A)  Csp2 F1F1F1S1F1F1F10 Csp2 
B)  Csp2 F1F1F1S1F1F1F10 C2p 
C)  C2p F1F1F1S1F1F1F10 C2p 
D)  Csp3 F1F1F1S1F1F1F10 Csp3 
A)  Csp2 F1F1F1S1F1F1F10 Csp2 
B)  Csp2 F1F1F1S1F1F1F10 C2p 
C)  C2p F1F1F1S1F1F1F10 C2p 
D)  Csp3 F1F1F1S1F1F1F10 Csp3

Question 2

What orbitals are used to form the indicated bond?

Accepted Answer

A)  sp3 
B)  sp2 
C)  p 
D)  sp3 and sp2 
A)  sp3 
B)  sp2 
C)  p 
D)  sp3 and sp2

Question 3

What is the IUPAC name of the following compound?

Accepted Answer

A)  3-Bromo-1-chloro-4-toluene 
B)  2-Bromo-4-chlorotoluene 
C)  4-Chloro-2-bromo-1-toluene 
D)  2-Bromo-4-chloroanisole 
A)  3-Bromo-1-chloro-4-toluene 
B)  2-Bromo-4-chlorotoluene 
C)  4-Chloro-2-bromo-1-toluene 
D)  2-Bromo-4-chloroanisole

Question 4

Which of the following compounds is aromatic?

Accepted Answer

A)  I 
B)  II 
C)  III 
D)  IV 
A)  I 
B)  II 
C)  III 
D)  IV

Question 5

What is the IUPAC name of the following compound?

Accepted Answer

A)  2-Nitro-5-carboxychlorobenzene 
B)  2-Chloro-4-carboxynitrobenzene 
C)  2-Chloro-1-nitro-4-benzoic acid 
D)  3-Chloro-4-nitrobenzoic acid 
A)  2-Nitro-5-carboxychlorobenzene 
B)  2-Chloro-4-carboxynitrobenzene 
C)  2-Chloro-1-nitro-4-benzoic acid 
D)  3-Chloro-4-nitrobenzoic acid

Question 6

What compound is consistent with the following 1H NMR spectrum?

Accepted Answer

A)  phenol 
B)  anisole 
C)  4-bromoanisole 
D)  4-bromotoluene 
A)  phenol 
B)  anisole 
C)  4-bromoanisole 
D)  4-bromotoluene

Question 7

Which of the following statements about benzene is true?

Accepted Answer

A)  Benzene is a saturated hydrocarbon. 
B)  Benzene undergoes addition reactions. 
C)  Benzene has five degrees of unsaturation. 
D)  Benzene undergoes substitution reactions. 
A)  Benzene is a saturated hydrocarbon. 
B)  Benzene undergoes addition reactions. 
C)  Benzene has five degrees of unsaturation. 
D)  Benzene undergoes substitution reactions.

Question 8

What is the structure of a compound of molecular formula C10H14O2 that shows a strong IR absorption at 3150 F1F1F1S1F1F1F10 2850 cm-1 and gives the following 1H NMR absorptions: 1.4 (triplet, 6H); 4.0 (quartet, 4H); and 6.8 (singlet, 4H) ppm.

Accepted Answer

A)  I 
B)  II 
C)  III 
D)  IV 
A)  I 
B)  II 
C)  III 
D)  IV

Question 9

What is the correct structure for toluene?

Accepted Answer

A)  I 
B)  II 
C)  III 
D)  IV 
A)  I 
B)  II 
C)  III 
D)  IV

Question 10

How many different proton signals would the following compound show in its 1H NMR spectrum?

Accepted Answer

A)  1 
B)  3 
C)  5 
D)  6 
A)  1 
B)  3 
C)  5 
D)  6

Question 11

What is the name of the following compound?

Accepted Answer

A)  meta-bromophenol 
B)  para-hydroxybenzene 
C)  3-bromoanisole 
D)  6-methoxy-2-bromobenzene 
A)  meta-bromophenol 
B)  para-hydroxybenzene 
C)  3-bromoanisole 
D)  6-methoxy-2-bromobenzene

Question 12

Which of the following compounds is aromatic?

Accepted Answer

A)  I 
B)  II 
C)  III 
D)  IV 
A)  I 
B)  II 
C)  III 
D)  IV

Question 13

Where do the protons in benzene appear in the 1H NMR spectrum?

Accepted Answer

A)  Around 1600 cm-1 
B)  Around 120 ppm 
C)  Around 0 ppm 
D)  Around 7 ppm 
A)  Around 1600 cm-1 
B)  Around 120 ppm 
C)  Around 0 ppm 
D)  Around 7 ppm

Question 14

Which of the following ions is aromatic?

Accepted Answer

A)  I 
B)  II 
C)  III 
D)  IV 
A)  I 
B)  II 
C)  III 
D)  IV

Question 15

What is the correct assignment of the number of signals in the 13C NMR spectra of the following disubstituted benzene derivatives?

Accepted Answer

A)  I = 3 signals; II = 3 signals; III = 2 signals. 
B)  I = 3 signals; II = 4 signals; III = 2 signals. 
C)  I = 6 signals; II = 6 signals; III = 6 signals. 
D)  I = 3 signals; II = 4 signals; III = 3 signals. 
A)  I = 3 signals; II = 3 signals; III = 2 signals. 
B)  I = 3 signals; II = 4 signals; III = 2 signals. 
C)  I = 6 signals; II = 6 signals; III = 6 signals. 
D)  I = 3 signals; II = 4 signals; III = 3 signals.

Question 16

What is the correct structure for 1-bromo-2,4-dimethoxybenzene?

Accepted Answer

A)  I 
B)  II 
C)  III 
D)  IV 
A)  I 
B)  II 
C)  III 
D)  IV

Question 17

How many 13CNMR signals does the following compound exhibit?

Accepted Answer

A)  4 
B)  5 
C)  6 
D)  8 
A)  4 
B)  5 
C)  6 
D)  8

Question 18

What is the correct assignment of the names of the following substituted benzenes?

Accepted Answer

A)  I = Styrene; II = aniline; III = anisole. 
B)  I = Toluene; II = anisole; III = styrene. 
C)  I = Styrene; II = anisole; III = phenol. 
D)  I = Toluene; II = aniline; III = anisole. 
A)  I = Styrene; II = aniline; III = anisole. 
B)  I = Toluene; II = anisole; III = styrene. 
C)  I = Styrene; II = anisole; III = phenol. 
D)  I = Toluene; II = aniline; III = anisole.

Question 19

What is the correct structure for para-bromotoluene?

Accepted Answer

A)  I 
B)  II 
C)  III 
D)  IV 
A)  I 
B)  II 
C)  III 
D)  IV

Question 20

What is the correct structure for aniline?

Accepted Answer

A)  I 
B)  II 
C)  III 
D)  IV 
A)  I 
B)  II 
C)  III 
D)  IV

Exam 17: Benzene and Aromatic Compounds

What orbitals are used to form the bond indicated in the following molecule?

What orbitals are used to form the indicated bond?

What is the IUPAC name of the following compound?

Which of the following compounds is aromatic?

What is the IUPAC name of the following compound?

What compound is consistent with the following 1H NMR spectrum?

Which of the following statements about benzene is true?

What is the structure of a compound of molecular formula C10H14O2 that shows a strong IR absorption at 3150  2850 cm-1 and gives the following 1H NMR absorptions: 1.4 (triplet, 6H); 4.0 (quartet, 4H); and 6.8 (singlet, 4H) ppm.

What is the correct structure for toluene?

How many different proton signals would the following compound show in its 1H NMR spectrum?

What is the name of the following compound?

Which of the following compounds is aromatic?

Where do the protons in benzene appear in the 1H NMR spectrum?

Which of the following ions is aromatic?

What is the correct assignment of the number of signals in the 13C NMR spectra of the following disubstituted benzene derivatives?

What is the correct structure for 1-bromo-2,4-dimethoxybenzene?

How many 13CNMR signals does the following compound exhibit?

What is the correct assignment of the names of the following substituted benzenes?

What is the correct structure for para-bromotoluene?

What is the correct structure for aniline?

Structure and Bonding

Acids and Bases

Introduction to Organic Molecules and Functional Groups

Alkanes

Stereochemistry

Understanding Organic Reactions

Alkyl Halides and Nucleophilic Substitution

Alkyl Halides and Elimination Reactions

Alcohols, Ethers and Epoxides

Alkenes

Alkynes

Oxidation and Reduction

Mass Spectrometry and Infrared Spectroscopy

Nuclear Magnetic Resonance Spectroscopy

Radical Reactions

Conjugation, Resonance, and Dienes

Electrophilic Aromatic Substitution

Carboxylic Acids and the Acidity of the O-H Bond

Introduction to Carbonyl Chemistry; Organometallic Reagents; Oxidation and Reduction

Aldehydes and Ketones Nucleophilic Addition

Carboxylic Acids and Derivatives

Substitution Reactions of Carbonyl Compounds at the Alpha-Carbon

Carbonyl Condensation Reactions

Amines

Carbon-Carbon Bond Forming Reactions in Organic Synthesis

Pericyclic Reactions

Carbohydrates

Amino Acids and Proteins

Lipids

Synthetic Polymers

Filters

What compound is consistent with the following ¹H NMR spectrum?

What is the structure of a compound of molecular formula C₁₀H₁₄O₂ that shows a strong IR absorption at 3150  2850 cm^-1 and gives the following ¹H NMR absorptions: 1.4 (triplet, 6H); 4.0 (quartet, 4H); and 6.8 (singlet, 4H) ppm.

How many different proton signals would the following compound show in its ¹H NMR spectrum?

Where do the protons in benzene appear in the ¹H NMR spectrum?

What is the correct assignment of the number of signals in the ¹³C NMR spectra of the following disubstituted benzene derivatives?

How many ¹³CNMR signals does the following compound exhibit?