Question 1

What is the name of the following compound?

Accepted Answer

A) 2,6-Dimethylbenzene 
B) 5-Methyltoluene 
C) Anisole 
D) 1,3-Dimethylbenzene 
A) 2,6-Dimethylbenzene 
B) 5-Methyltoluene 
C) Anisole 
D) 1,3-Dimethylbenzene D

Question 2

Rank the following compounds in order of decreasing acidity, starting with the most acidic.

Accepted Answer

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

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 A

Question 4

What is the correct assignment of the names of the following aromatic heterocycles?

Accepted Answer

A) I = pyridine; II = pyrimidine; III = furan. 
B) I = pyrimidine; II =pyrrole; III = furan. 
C) I = pyridine; II = pyrrole; III = furan. 
D) I = pyrimidine; II = pyrrole; III = tetrahydrofuran. 
A) I = pyridine; II = pyrimidine; III = furan. 
B) I = pyrimidine; II =pyrrole; III = furan. 
C) I = pyridine; II = pyrrole; III = furan. 
D) I = pyrimidine; II = pyrrole; III = tetrahydrofuran.

Question 5

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 6

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 7

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 8

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 9

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 10

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 11

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 12

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 13

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 14

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 p 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 p electron system is not continuous.

Question 15

What is the IUPAC name of the following compound?

Accepted Answer

A) 3,6-Dichloroaniline 
B) 2,5-Dichloroaniline 
C) 2,5-Dichloroaminobenzene 
D) 2,5-Dichloroanisole 
A) 3,6-Dichloroaniline 
B) 2,5-Dichloroaniline 
C) 2,5-Dichloroaminobenzene 
D) 2,5-Dichloroanisole

Question 16

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 17

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 18

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 19

Which of the following compounds is not aromatic?

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 is the name of the following compound?

Rank the following compounds in order of decreasing acidity, starting with the most acidic.

Which of the following ions is aromatic?

What is the correct assignment of the names of the following aromatic heterocycles?

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 compounds is aromatic?

How many 13CNMR signals does the following compound exhibit?

What is the IUPAC name of the following compound?

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

Which of the following compounds is aromatic?

What orbitals are used to form the indicated bond?

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 toluene?

Why is the following compound not aromatic?

What is the IUPAC name of the following compound?

What is the name of the following compound?

Which of the following is not a criterion for antiaromaticity?

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

Which of the following compounds is not aromatic?

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 Related Compounds

Alkenes

Alkynes

Oxidation and Reduction

Mass Spectrometry and Infrared Spectroscopy

Nuclear Magnetic Resonance Spectroscopy

Radical Reactions

Conjugation, Resonance, and Dienes

Reactions of Aromatic Compounds

Carboxylic Acids and the Acidity of the O-H Bond

Introduction to Carbonyl Chemistry;

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

Synthetic Polymers

Lipids

Filters

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?

How many ¹³CNMR signals does the following compound exhibit?

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