Question 1

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 2

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 3

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 4

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 5

Why is the following compound not aromatic?

Accepted Answer

A) It has 4n pi electrons. 
B) It is not cyclic. 
C) It has 4n+2 pi electrons. 
D) The pi electron system is not continuous. 
A) It has 4n pi electrons. 
B) It is not cyclic. 
C) It has 4n+2 pi electrons. 
D) The pi electron system is not continuous.

Question 6

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 7

What is the IUPAC name of the following compound?

Accepted Answer

A) 1-Chloro-4-ethyl-3-propylbenzene 
B) 1-Chloro-4-ethyl-5-propylbenzene 
C) 4-Chloro-1-ethyl-2-propylbenzene 
D) 4-Chloro-2-propyltoluene 
A) 1-Chloro-4-ethyl-3-propylbenzene 
B) 1-Chloro-4-ethyl-5-propylbenzene 
C) 4-Chloro-1-ethyl-2-propylbenzene 
D) 4-Chloro-2-propyltoluene

Question 8

Which of the following is not one of the Hückel's criteria for aromaticity?

Accepted Answer

A) The molecule must be cyclic. 
B) The molecule must be planar. 
C) The molecule must be completely conjugated. 
D) The molecule must have 4n pi electrons. 
A) The molecule must be cyclic. 
B) The molecule must be planar. 
C) The molecule must be completely conjugated. 
D) The molecule must have 4n pi electrons.

Question 9

Which of the following is not a criterion for antiaromaticity?

Accepted Answer

A) The molecule must be cyclic. 
B) The molecule must have (4n + 2)pi electrons. 
C) The molecule must be planar. 
D) The molecule must be completely conjugated. 
A) The molecule must be cyclic. 
B) The molecule must have (4n + 2)pi electrons. 
C) The molecule must be planar. 
D) The molecule must be completely conjugated.

Question 10

Which of the following heterocycles is not aromatic?

Accepted Answer

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

Question 11

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 12

What is the structure of a compound of molecular formula C10H14O2 that shows a strong IR absorption at 3150 ¾2850 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 13

Which of the following statements about the structure of benzene is not true?

Accepted Answer

A) Benzene is planar. 
B) Benzene has three short double bonds alternating with three longer single bonds. 
C) The electrons in the pi bonds are delocalized around the ring. 
D) Benzene has six pi electrons. 
A) Benzene is planar. 
B) Benzene has three short double bonds alternating with three longer single bonds. 
C) The electrons in the pi bonds are delocalized around the ring. 
D) Benzene has six pi electrons.

Question 14

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

Accepted Answer

A) I = Phenol; II = anisole; III = toluene 
B) I = Benzaldehyde; II = phenol; III = anisole 
C) I = Benzaldehyde; II = phenol; III = toluene 
D) I = Phenol; II = anisole; III = styrene 
A) I = Phenol; II = anisole; III = toluene 
B) I = Benzaldehyde; II = phenol; III = anisole 
C) I = Benzaldehyde; II = phenol; III = toluene 
D) I = Phenol; II = anisole; III = styrene

Question 15

Why is the following compound not aromatic?

Accepted Answer

A) It has 4n electrons. 
B) It is not cyclic. 
C) It has 4n+2 electrons. 
D) The pi electron system is not continuous. 
A) It has 4n electrons. 
B) It is not cyclic. 
C) It has 4n+2 electrons. 
D) The pi electron system is not continuous.

Question 16

What is the IUPAC name of the following compound?

Accepted Answer

A) o-nitroanisole 
B) m-nitroanisole 
C) p-nitroanisole 
D) 2-nitroaniline 
A) o-nitroanisole 
B) m-nitroanisole 
C) p-nitroanisole 
D) 2-nitroaniline

Question 17

What is the IUPAC name of the following compound?

Accepted Answer

A) o-nitrotoluene 
B) m-nitrotoluene 
C) p-nitrotoluene 
D) 3-nitroanisole 
A) o-nitrotoluene 
B) m-nitrotoluene 
C) p-nitrotoluene 
D) 3-nitroanisole

Question 18

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 19

What is the correct assignment of the names of the following fused aromatic compounds?

Accepted Answer

A) I = naphthalene; II = anthracene; III = phenanthrene 
B) I = naphthalene; II = phenanthrene; III = anthracene 
C) I = naphthalene; II = phenanthrene; III = benzo[a]pyrene 
D) I = anthracene; II = naphthalene; III = phenanthrene 
A) I = naphthalene; II = anthracene; III = phenanthrene 
B) I = naphthalene; II = phenanthrene; III = anthracene 
C) I = naphthalene; II = phenanthrene; III = benzo[a]pyrene 
D) I = anthracene; II = naphthalene; III = phenanthrene

Question 20

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

Exam 15: Benzene and Aromatic Compounds

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

What is the correct structure for toluene?

Which of the following ions is aromatic?

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

Why is the following compound not aromatic?

What orbitals are used to form the indicated bond?

What is the IUPAC name of the following compound?

Which of the following is not one of the Hückel's criteria for aromaticity?

Which of the following is not a criterion for antiaromaticity?

Which of the following heterocycles is not aromatic?

Which of the following compounds is aromatic?

What is the structure of a compound of molecular formula C10H14O2 that shows a strong IR absorption at 3150 ¾2850 cm-1 and gives the following 1H NMR absorptions: 1.4 (triplet,6H); 4.0 (quartet,4H); and 6.8 (singlet,4H)ppm?

Which of the following statements about the structure of benzene is not true?

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

Why is the following compound not aromatic?

What is the IUPAC name of the following compound?

What is the IUPAC name of the following compound?

What orbitals are used to form the indicated bond?

What is the correct assignment of the names of the following fused aromatic compounds?

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

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 Related Compounds

Alkenes and Addition Reactions

Alkynes and Synthesis

Oxidation and Reduction

Radical Reactions

Conjugation,resonance,and Dienes

Reactions of Aromatic Compounds

Introduction to Carbonyl Chemistry; Organometallic Reagents; Oxidation and Reduction

Aldehydes and Ketones - Nucleophilic Addition

Carboxylic Acids and the Acidity of the O-H Bond

Carboxylic Acids and Their Derivatives Nucleophilic Acyl Substitution

Substitution Reactions of Carbonyl Compounds at the a Carbon

Carbonyl Condensation Reactions

Amines

Carbon-Carbon Bond-Forming Reactions in Organic Synthesis

Pericyclic Reactions

Carbohydrates

Amino Acids and Proteins

Synthetic Polymers

Lipids

Spectroscopy A: Mass Spectrometry

Spectroscopy B: Infrared Spectroscopy

Spectroscopy C: Nuclear Magnetic Resonance Spectroscopy

Filters

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

What is the structure of a compound of molecular formula C₁₀H₁₄O₂ that shows a strong IR absorption at 3150 ¾2850 cm^-1 and gives the following ¹H NMR absorptions: 1.4 (triplet,6H); 4.0 (quartet,4H); and 6.8 (singlet,4H)ppm?