Question 1

What are the relative positions of the substituents in the following structure?

Accepted Answer

A)  anti 
B)  meta 
C)  ortho 
D)  para 
A)  anti 
B)  meta 
C)  ortho 
D)  para B

Question 2

What is the IUPAC name of the following compound?

Accepted Answer

A)  2,4-dibromotoluene 
B)  2,4-dibromophenol 
C)  2,4-dibromohydroxybenzene 
D)  4,6-dibromophenol 
A)  2,4-dibromotoluene 
B)  2,4-dibromophenol 
C)  2,4-dibromohydroxybenzene 
D)  4,6-dibromophenol B

Question 3

What are the relative positions of the substituents in the following structure?

Accepted Answer

A)  anti 
B)  meta 
C)  ortho 
D)  para 
A)  anti 
B)  meta 
C)  ortho 
D)  para D

Question 4

What are the two major organic products obtained from the following reaction?

Accepted Answer

The answer of What are the two major organic products...

Question 5

What is the hybridization of the nitrogen atom of pyridine?

Accepted Answer

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

Question 6

Which of the following ions is aromatic?

Accepted Answer

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

Question 7

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

Accepted Answer

A)  1 = phenol; 2 = aniline; 3 = anisole 
B)  1 = benzaldehyde; 2 = anisole; 3 = toluene 
C)  1 = anisole; 2 = xylene; 3 = toluene 
D)  1 = anisole; 2 = aniline; 3 = toluene 
A)  1 = phenol; 2 = aniline; 3 = anisole 
B)  1 = benzaldehyde; 2 = anisole; 3 = toluene 
C)  1 = anisole; 2 = xylene; 3 = toluene 
D)  1 = anisole; 2 = aniline; 3 = toluene

Question 8

Which of the following molecules is the most acidic?

Accepted Answer

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

Question 9

What is the major organic product obtained from the following reaction?

Accepted Answer

The answer of What is the major organic product obtained...

Question 10

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

Accepted Answer

A)  The compound must be cyclic 
B)  The compound must have one p-orbital on each atom of a ring 
C)  The compound must be planar or nearly planar so that there is a continuous overlap of p orbitals 
D)  The compound must have a closed loop of six pi electrons 
A)  The compound must be cyclic 
B)  The compound must have one p-orbital on each atom of a ring 
C)  The compound must be planar or nearly planar so that there is a continuous overlap of p orbitals 
D)  The compound must have a closed loop of six pi electrons

Question 11

Which of the following compounds undergoes heterolytic carbon-halogen bond cleavage to form a stable organic cation?

Accepted Answer

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

Question 12

Which of the following compounds is aromatic?

Accepted Answer

A)  ethane 
B)  cyclobutadiene 
C)  benzene 
D)  cyclooctatetraene 
A)  ethane 
B)  cyclobutadiene 
C)  benzene 
D)  cyclooctatetraene

Question 13

Which of the following does not undergo oxidation in the presence of H2CrO4?

Accepted Answer

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

Question 14

Which of the following has the compounds shown in the correct order of decreasing acidity (i.e., more acidic > less acidic)?

Accepted Answer

A)  1 > 2 > 3 
B)  2 > 3 > 1 
C)  3 > 2 > 1 
D)  1 > 3 > 2 
A)  1 > 2 > 3 
B)  2 > 3 > 1 
C)  3 > 2 > 1 
D)  1 > 3 > 2

Question 15

What is the major organic product obtained from the following reaction?

Accepted Answer

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

Question 16

What is the approximate length of the carbon-carbon bonds in benzene?

Accepted Answer

A)  110 pm 
B)  121 pm 
C)  139 pm 
D)  156 pm 
A)  110 pm 
B)  121 pm 
C)  139 pm 
D)  156 pm

Question 17

Which of the following has the compounds shown in the correct order of decreasing acidity (i.e., more acidic > less acidic)?

Accepted Answer

A)  1 > 2 > 3 
B)  2 > 3 > 1 
C)  3 > 2 > 1 
D)  1 > 3 > 2 
A)  1 > 2 > 3 
B)  2 > 3 > 1 
C)  3 > 2 > 1 
D)  1 > 3 > 2

Question 18

Which of the following has the compounds shown in the correct order of decreasing acidity (i.e., more acidic > less acidic)?

Accepted Answer

A)  1 > 2 > 3 
B)  2 > 3 > 1 
C)  3 > 2 > 1 
D)  2 > 1 > 3 
A)  1 > 2 > 3 
B)  2 > 3 > 1 
C)  3 > 2 > 1 
D)  2 > 1 > 3

Question 19

What is the major organic product obtained from the following reaction?

Accepted Answer

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

Question 20

Which of the following represents the energy levels of the molecular orbitals of benzene?

Accepted Answer

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

Exam 21: Benzene and the Concept of Aromaticity

What are the relative positions of the substituents in the following structure?

What is the IUPAC name of the following compound?

What are the relative positions of the substituents in the following structure?

What are the two major organic products obtained from the following reaction?

What is the hybridization of the nitrogen atom of pyridine?

Which of the following ions is aromatic?

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

Which of the following molecules is the most acidic?

What is the major organic product obtained from the following reaction?

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

Which of the following compounds undergoes heterolytic carbon-halogen bond cleavage to form a stable organic cation?

Which of the following compounds is aromatic?

Which of the following does not undergo oxidation in the presence of H2CrO4?

Which of the following has the compounds shown in the correct order of decreasing acidity (i.e., more acidic > less acidic)?

What is the major organic product obtained from the following reaction?

What is the approximate length of the carbon-carbon bonds in benzene?

Which of the following has the compounds shown in the correct order of decreasing acidity (i.e., more acidic > less acidic)?

Which of the following has the compounds shown in the correct order of decreasing acidity (i.e., more acidic > less acidic)?

What is the major organic product obtained from the following reaction?

Which of the following represents the energy levels of the molecular orbitals of benzene?

Covalent Bonding and Shapes of Molecules

Alkanes and Cycloalkanes

Stereoisomerism and Chirality

Acids and Bases

Alkenes: Bonding, Nomenclature, and Properties

Reactions of Alkenes

Alkynes

Haloalkanes, Halogenation, and Radical Reactions

Nucleophilic Substitution and Beta-Elimination

Alcohols

Ethers, Epoxides, and Sulfides

Infrared Spectroscopy

Nuclear Magnetic Resonance Spectroscopy

Mass Spectrometry

An Introduction to Organometallic Compounds

Aldehydes and Ketones

Carboxylic Acids

Functional Derivatives of Carboxylic Acids

Enolate Anions and Enamines

Dienes, Conjugated Systems, and Pericyclic Reactions

Reactions of Benzene and Its Derivatives

Filters

Which of the following does not undergo oxidation in the presence of H₂CrO₄?