Question 1

According to molecular orbital theory, how many $\pi$-bonding molecular orbitals does benzene have?

Accepted Answer

A)  1 
B)  2 
C)  3 
D)  4 
E)  5 
A)  1 
B)  2 
C)  3 
D)  4 
E)  5 C

Question 2

A compound with molecular formula C9H12O displays the following 1H NMR and 13C NMR spectra. Propose a structure for this compound.

Accepted Answer

Question 3

What is the common name for the following compound?

Accepted Answer

m-xylene

Question 4

Using a Frost circle, draw the molecular orbital energy diagram for the tropylium cation and predict if it is aromatic.

Accepted Answer

@#IMG-DLM&_TB4454_00

Question 5

Using a Frost circle, draw the molecular orbital energy diagram for the cyclopentadienyl anion and predict if it is aromatic.

Accepted Answer

@#IMG-DLM&_TB4454_00

Question 6

Provide the product for the following reaction.

Accepted Answer

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

Question 7

Which one 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 8

Using a Frost circle, draw the molecular orbital energy diagram for the cyclopropenyl anion and predict if it is aromatic.

Accepted Answer

@#IMG-DLM&_TB4454_00

Question 9

Which one of the following compounds is antiaromatic?

Accepted Answer

A)  I 
B)  II 
C)  III 
D)  IV 
E)  none of these 
A)  I 
B)  II 
C)  III 
D)  IV 
E)  none of these

Question 10

Provide the reagents necessary to carry out the following conversion.

Accepted Answer

1. NBS/@#LAT-DLM&
2.

Question 11

Which one of the following compounds is most acidic?

Accepted Answer

A)  I 
B)  II 
C)  III 
D)  IV 
E)  none of these 
A)  I 
B)  II 
C)  III 
D)  IV 
E)  none of these

Question 12

Which one of the following compounds is most acidic?

Accepted Answer

A)  I 
B)  II 
C)  III 
D)  I & III 
E)  II & III 
A)  I 
B)  II 
C)  III 
D)  I & III 
E)  II & III

Question 13

What is the main difference between an aromatic and antiaromatic compound?

Accepted Answer

A)  Aromatic compounds must be cyclic and planar, but not antiaromatic compounds 
B)  Aromatic compounds must be monocyclic. 
C)  Antiaromatic compounds must have a conjugated system with a p orbital at every vertex 
D)  Aromatic compounds must satisfy Hückel's rule. 
E)  none of these 
A)  Aromatic compounds must be cyclic and planar, but not antiaromatic compounds 
B)  Aromatic compounds must be monocyclic. 
C)  Antiaromatic compounds must have a conjugated system with a p orbital at every vertex 
D)  Aromatic compounds must satisfy Hückel's rule. 
E)  none of these

Question 14

Provide the reagent(s) necessary to convert toluene to benzoic acid.

Accepted Answer

A)  Na2Cr2O7/H2SO4/H2O 
B)  1. NBS, $\Delta$ 2.NaOH 
C)  1. LiAlH4 2. H3O+ 
D)  H2, Pd 
E)  1. CO2, 2. H3O+ 
A)  Na2Cr2O7/H2SO4/H2O 
B)  1. NBS, $\Delta$ 2.NaOH 
C)  1. LiAlH4 2. H3O+ 
D)  H2, Pd 
E)  1. CO2, 2. H3O+

Question 15

Predict the product for the following reaction.

Accepted Answer

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

Question 16

Both pyridine and pyrrole are nitrogen containing aromatic heterocyclic compounds. When treated with HCl, only pyridine forms the hydrochloride salt, whereas pyrrole is unreactive. Provide an explanation for this observed reactivity.

Accepted Answer

In pyridine, the nonbonding electron pai

Question 17

Identify the functional group in styrene.

Accepted Answer

A)  ether 
B)  alkene 
C)  carboxylic acid 
D)  aldehyde 
E)  ketone 
A)  ether 
B)  alkene 
C)  carboxylic acid 
D)  aldehyde 
E)  ketone

Question 18

Which one 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 19

Give the common name for o-xylene.

Accepted Answer

A)  hydroxybenzene 
B)  aminobenzene 
C)  1,2-dimethylbenzene 
D)  ethylbenzene 
E)  1,3-dimethylbenzene 
A)  hydroxybenzene 
B)  aminobenzene 
C)  1,2-dimethylbenzene 
D)  ethylbenzene 
E)  1,3-dimethylbenzene

Question 20

Provide the structures of the intermediates and final product in the following reaction sequence.

Accepted Answer

The answer of Provide the structures of the intermediates and...

Exam 17: Aromatic Compounds

According to molecular orbital theory, how many π\piπ -bonding molecular orbitals does benzene have?

A compound with molecular formula C9H12O displays the following 1H NMR and 13C NMR spectra. Propose a structure for this compound.

What is the common name for the following compound?

Using a Frost circle, draw the molecular orbital energy diagram for the tropylium cation and predict if it is aromatic.

Using a Frost circle, draw the molecular orbital energy diagram for the cyclopentadienyl anion and predict if it is aromatic.

Provide the product for the following reaction.

Which one of the following compounds is aromatic?

Using a Frost circle, draw the molecular orbital energy diagram for the cyclopropenyl anion and predict if it is aromatic.

Which one of the following compounds is antiaromatic?

Provide the reagents necessary to carry out the following conversion.

Which one of the following compounds is most acidic?

Which one of the following compounds is most acidic?

What is the main difference between an aromatic and antiaromatic compound?

Provide the reagent(s) necessary to convert toluene to benzoic acid.

Predict the product for the following reaction.

Both pyridine and pyrrole are nitrogen containing aromatic heterocyclic compounds. When treated with HCl, only pyridine forms the hydrochloride salt, whereas pyrrole is unreactive. Provide an explanation for this observed reactivity.

Identify the functional group in styrene.

Which one of the following compounds is aromatic?

Give the common name for o-xylene.

Provide the structures of the intermediates and final product in the following reaction sequence.

A Review of General Chemistry: Electrons, Bonds, and Molecular Properties

Molecular Representations

Acids and Bases

Alkanes and Cycloalkanes

Stereoisomerism

Chemical Reactivity and Mechanisms

Alkyl Halides: Nucleophilic Substitution and Elimination Reactions

Addition Reactions of Alkenes

Alkynes

Radical Reactions

Synthesis

Alcohols and Phenols

Ethers and Epoxides; Thiols and Sulfides

Infrared Spectroscopy and Mass Spectrometry

Nuclear Magnetic Resonance Spectroscopy

Conjugated Pi Systems and Pericyclic Reactions

Aromatic Substitution Reactions

Aldehydes and Ketones

Carboxylic Acids and Their Derivatives

Alpha Carbon Chemistry: Enols and Enolates

Amines

Introduction to Organometallic Compounds

Carbohydrates

Amino Acids, Peptides, and Proteins

Lipids

Synthetic Polymers

Filters

According to molecular orbital theory, how many $\pi$ -bonding molecular orbitals does benzene have?

A compound with molecular formula C₉H₁₂O displays the following ¹H NMR and ¹³C NMR spectra. Propose a structure for this compound.