Question 1

Which cyclization(s)should occur with an increase in pi-electron energy?

Accepted Answer

A) I 
B) II 
C) III 
D) IV 
E) All of these choices. 
A) I 
B) II 
C) III 
D) IV 
E) All of these choices.

Question 2

The complete name for the following compound is:

Accepted Answer

A) sec-Hexylbenzene 
B) 2-Phenylhexane 
C) (R)-2-Phenylhexane 
D) (S)-2-Phenylhexane 
E) Butylmethylphenylmethane 
A) sec-Hexylbenzene 
B) 2-Phenylhexane 
C) (R)-2-Phenylhexane 
D) (S)-2-Phenylhexane 
E) Butylmethylphenylmethane

Question 3

Which of the following substances,formula C8H9Br,might exhibit the following 1H NMR spectrum? 
singlet,$\delta$ 2.45
Singlet,$\delta$ 2.5
Multiplet,$\delta$ 7.35

Accepted Answer

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

Question 4

In which case is the indicated unshared pair of electrons NOT a contributor to the $\pi$ aromatic system?

Accepted Answer

A) I 
B) II 
C) III 
D) IV 
E) None of these choices. 
A) I 
B) II 
C) III 
D) IV 
E) None of these choices.

Question 5

Which of the following would you expect to be aromatic?

Accepted Answer

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

Question 6

In the molecular orbital model of cyclobutadiene,how many $\pi$-bonding molecular orbitals are there?

Accepted Answer

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

Question 7

Monocyclic compounds with alternating single and double bonds are called ___.

Accepted Answer

The answer of Monocyclic compounds with alternating single and double...

Question 8

Which of the following statements regarding the cycloheptatrienyl anion is correct?

Accepted Answer

A) It is aromatic. 
B) It is not aromatic. 
C) It obeys Hückel's rule. 
D) It undergoes reactions characteristic of benzene. 
E) It has a closed shell of 6 pi electrons. 
A) It is aromatic. 
B) It is not aromatic. 
C) It obeys Hückel's rule. 
D) It undergoes reactions characteristic of benzene. 
E) It has a closed shell of 6 pi electrons.

Question 9

Which of these would you expect to have significant resonance stabilization energy?

Accepted Answer

A) I 
B) II 
C) III 
D) All of these choices. 
E) None of these choices. 
A) I 
B) II 
C) III 
D) All of these choices. 
E) None of these choices.

Question 10

Give the IUPAC name for the following substance:

Accepted Answer

2-methyl-4

Question 11

In the molecular orbital model of which of the following substance(s)are non-bonding orbitals found?

Accepted Answer

A) 1,3-Cyclobutadiene 
B) Cyclopentadienyl anion 
C) 1,3,5,7-Cyclooctatetraene 
D) Two of these choices. 
E) All of these choices. 
A) 1,3-Cyclobutadiene 
B) Cyclopentadienyl anion 
C) 1,3,5,7-Cyclooctatetraene 
D) Two of these choices. 
E) All of these choices.

Question 12

The correct name for the compound shown below is:

Accepted Answer

A) 3-bromobenzene 
B) 4-bromobenzene 
C) m-bromobenzene 
D) o-bromotoluene 
E) bromomethylbenzene 
A) 3-bromobenzene 
B) 4-bromobenzene 
C) m-bromobenzene 
D) o-bromotoluene 
E) bromomethylbenzene

Question 13

Cagelike molecules with the geometry of a truncated icosahedron are called ___.

Accepted Answer

The answer of Cagelike molecules with the geometry of a...

Question 14

Which of the following would you expect to be antiaromatic?

Accepted Answer

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

Question 15

A compound has the formula C8H9Br.Its 1H NMR spectrum consists of: doublet,$\delta$ 2.0
Quartet,$\delta$ 5.15
Multiplet,$\delta$ 7.35
The IR spectrum shows two peaks in the 680-840 cm-1 region; one is between 690 and 710 cm-1 and the other is between 730 and 770 cm-1.Which is a possible structure for the compound?

Accepted Answer

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

Question 16

In the molecular orbital model of the cyclopentadienyl cation,how many $\pi$-bonding molecular orbitals are there?

Accepted Answer

A) 6 
B) 5 
C) 4 
D) 3 
E) 2 
A) 6 
B) 5 
C) 4 
D) 3 
E) 2

Question 17

Which of these would you expect to have significant resonance stabilization energy?

Accepted Answer

A) I 
B) II 
C) III 
D) All of these choices. 
E) None of these choices. 
A) I 
B) II 
C) III 
D) All of these choices. 
E) None of these choices.

Question 18

4-Bromomethyl-2-nitroanisole is:

Accepted Answer

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

Question 19

Briefly explain why the aromatic hydrocarbon shown possesses a significant dipole moment.Use diagrams as needed to illustrate/clarify your answer.

Accepted Answer

@#IMG-DLM& The stable,low energy resonan

Question 20

In the molecular orbital model of cyclopentadienyl anion,how many pi electrons are in bonding molecular orbitals?

Accepted Answer

A) 6 
B) 5 
C) 4 
D) 3 
E) 2 
A) 6 
B) 5 
C) 4 
D) 3 
E) 2

Exam 14: Aromatic Compounds

Which cyclization(s)should occur with an increase in pi-electron energy?

The complete name for the following compound is:

Which of the following substances,formula C8H9Br,might exhibit the following 1H NMR spectrum? singlet, δ\deltaδ 2.45 Singlet, δ\deltaδ 2.5 Multiplet, δ\deltaδ 7.35

In which case is the indicated unshared pair of electrons NOT a contributor to the π\piπ aromatic system?

Which of the following would you expect to be aromatic?

In the molecular orbital model of cyclobutadiene,how many π\piπ -bonding molecular orbitals are there?

Monocyclic compounds with alternating single and double bonds are called ___.

Which of the following statements regarding the cycloheptatrienyl anion is correct?

Which of these would you expect to have significant resonance stabilization energy?

Give the IUPAC name for the following substance:

In the molecular orbital model of which of the following substance(s)are non-bonding orbitals found?

The correct name for the compound shown below is:

Cagelike molecules with the geometry of a truncated icosahedron are called ___.

Which of the following would you expect to be antiaromatic?

In the molecular orbital model of the cyclopentadienyl cation,how many π\piπ -bonding molecular orbitals are there?

Which of these would you expect to have significant resonance stabilization energy?

4-Bromomethyl-2-nitroanisole is:

Briefly explain why the aromatic hydrocarbon shown possesses a significant dipole moment.Use diagrams as needed to illustrate/clarify your answer.

In the molecular orbital model of cyclopentadienyl anion,how many pi electrons are in bonding molecular orbitals?

The Basics

Families of Carbon

Acids and Bases

Nomenclature and Conformations of Alkanes and Cycloalkanes

Stereochemistry

Nucleophilic Reactions

Alkenes and Alkynes I

Alkenes and Alkynes II

Nuclear Magnetic Resonance and Mass Spectrometry

Radical Reactions

Alcohols and Ethers

Alcohols From Carbonyl Compounds

Conjugated Unsaturated Systems

Reactions of Aromatic Compounds

Aldehydes and Ketones

Carboxylic Acids and Their Derivatives

Reactions at the Α Carbon of Carbonyl Compounds

Condensation and Conjugate Addition Reactions of Carbonyl Compounds

Amines

Transition Metal Complexes

Carbohydrates

Lipids

Amino Acids and Proteins

Nucleic Acids and Protein Synthesis

Filters

In which case is the indicated unshared pair of electrons NOT a contributor to the $\pi$ aromatic system? $In which case is the indicated unshared pair of electrons NOT a contributor to the \pi aromatic system?$

In the molecular orbital model of cyclobutadiene,how many $\pi$ -bonding molecular orbitals are there?

In the molecular orbital model of the cyclopentadienyl cation,how many $\pi$ -bonding molecular orbitals are there?