Question 1

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 2

In what type of orbital does the lone pair on the indicated N atom reside?

Accepted Answer

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

Question 3

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 4

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 5

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 6

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 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 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 9

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 10

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

Question 11

Which of the following molecules has the most acidic hydrogen atoms?

Accepted Answer

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

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

Accepted Answer

A) Csp2¾Csp2 
B) Csp2¾ C2p 
C) C2p¾C2p 
D) Csp3¾Csp3 
A) Csp2¾Csp2 
B) Csp2¾ C2p 
C) C2p¾C2p 
D) Csp3¾Csp3

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 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 15

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 16

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 17

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 18

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 19

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 20

What is the hybridization of the indicated N atom in the following compound?

Accepted Answer

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

Exam 15: Benzene and Aromatic Compounds

What is the IUPAC name of the following compound?

In what type of orbital does the lone pair on the indicated N atom reside?

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

What orbitals are used to form the indicated bond?

What is the IUPAC name of the following compound?

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 benzene is true?

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

Which of the following ions is aromatic?

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

Which of the following molecules has the most acidic hydrogen atoms?

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

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

Why is the following compound not aromatic?

Which of the following compounds is aromatic?

What is the correct structure for para-bromotoluene?

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

What is the correct structure for toluene?

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

What is the hybridization of the indicated N atom in the following compound?

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

Molecular Ion Peaks and Fragmentation Patterns

Analyzing Molecular Motion and Infrared Spectroscopy

Organic Spectroscopy Concepts

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?

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

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