Question 1

Which of the following would you expect to be aromatic?

Accepted Answer

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

Question 2

In the molecular orbital model of benzene,how many non-bonding molecular orbitals are there?

Accepted Answer

A)  1 
B)  2 
C)  3 
D)  4 
E)  0 
A)  1 
B)  2 
C)  3 
D)  4 
E)  0

Question 3

In the molecular orbital model of the cyclopentadienyl cation,how many pairs of degenerate  $\pi$-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 4

Application of the polygon-and-circle technique reveals that single electrons occupy each of the two nonbonding orbitals in the molecular orbital diagram of:

Accepted Answer

A)  Cyclobutadiene 
B)  Benzene 
C)  Cyclopropenyl cation 
D)  Cyclopentadienyl anion 
E)  Cycloheptatrienyl cation 
A)  Cyclobutadiene 
B)  Benzene 
C)  Cyclopropenyl cation 
D)  Cyclopentadienyl anion 
E)  Cycloheptatrienyl cation

Question 5

In the molecular orbital model of benzene,how many pairs of degenerate  $\pi$-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 6

In the molecular orbital model of benzene,how many pairs of degenerate  $\pi$-antibonding 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

Which isomer of C7H7Cl exhibits strong IR absorbances at 690 and 750 cm1?

Accepted Answer

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

Question 8

Hückel's Rule requires _________  $\pi$ electrons for an aromatic compound.

Accepted Answer

The answer of Hückel's Rule requires _________  $\pi$ electrons...

Question 9

Draw the structure corresponding to the following name: 3-nitro-4-iodoanisole

Accepted Answer

The answer of Draw the structure corresponding to the following...

Question 10

Which of the following statements regarding the cycloheptatrienyl radical 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 11

For which of the following substances,C9H10O,would the aromatic multiplet,in its 1H NMR spectrum,consist of two doublets?

Accepted Answer

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

Question 12

Which reagent(s)would serve as the basis for a simple chemical test that would distinguish between naphthalene and 2,4,6-decatriene?

Accepted Answer

A)  NaOH in H2O 
B)  KMnO4,OH - ,H2O 
C)  NaBH4,H2O 
D)  H2CrO4 
E)  None of these 
A)  NaOH in H2O 
B)  KMnO4,OH - ,H2O 
C)  NaBH4,H2O 
D)  H2CrO4 
E)  None of these

Question 13

Draw all significant resonance structures for pyridine,C6H5N

Accepted Answer

Question 14

The Lewis structures of both pyridine and pyrrole have an electron pair on the nitrogen atom,suggesting that both substances might possess basic properties.However,only pyridine reacts readily with HCl to form pyridinium chloride,while pyrrole is rather unreactive.Explain clearly,using relevant diagrams to illustrate/clarify your answer.

Accepted Answer

@#IMG-DLM& Both pyridine and pyrrole are known to

Question 15

The compound illustrated below is found to have the following signals in its broadband
decoupled C-13 spectra:
190.77,140.91,134.82,130.89 and 129.45  $\delta$
Using resonance theory,assign the C-13 peaks to the appropriate carbons.

Accepted Answer

The answer of The compound illustrated below is found to...

Question 16

In the molecular orbital model of the cyclopentadienyl cation,how many pairs of degenerate  $\pi$-antibonding 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 17

Draw the structure corresponding to the following name:
3-bromo 5-phenylaniline

Accepted Answer

The answer of Draw the structure corresponding to the following...

Question 18

Which of these species is aromatic?

Accepted Answer

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

Question 19

The pka of cyclopentadiene is found to be 16 while,by contrast,that of cycloheptatriene is
found to be 36.Explain the large difference found in the two pka values.

Accepted Answer

The 20 order of magnitude difference in

Question 20

In the molecular orbital model of the cyclopentadienyl cation,how many  $\pi$-antibonding 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

Exam 14: Aromatic Compounds

Which of the following would you expect to be aromatic?

In the molecular orbital model of benzene,how many non-bonding molecular orbitals are there?

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

Application of the polygon-and-circle technique reveals that single electrons occupy each of the two nonbonding orbitals in the molecular orbital diagram of:

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

In the molecular orbital model of benzene,how many pairs of degenerate π\piπ -antibonding molecular orbitals are there?

Which isomer of C7H7Cl exhibits strong IR absorbances at 690 and 750 cm1?

Hückel's Rule requires _________ π\piπ electrons for an aromatic compound.

Draw the structure corresponding to the following name: 3-nitro-4-iodoanisole

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

For which of the following substances,C9H10O,would the aromatic multiplet,in its 1H NMR spectrum,consist of two doublets?

Which reagent(s)would serve as the basis for a simple chemical test that would distinguish between naphthalene and 2,4,6-decatriene?

Draw all significant resonance structures for pyridine,C6H5N

The compound illustrated below is found to have the following signals in its broadband decoupled C-13 spectra: 190.77,140.91,134.82,130.89 and 129.45 δ\deltaδ Using resonance theory,assign the C-13 peaks to the appropriate carbons.

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

Draw the structure corresponding to the following name: 3-bromo 5-phenylaniline

Which of these species is aromatic?

The pka of cyclopentadiene is found to be 16 while,by contrast,that of cycloheptatriene is found to be 36.Explain the large difference found in the two pka values.

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

Carbon Compounds and Chemical Bonds

Representative Carbon Compounds: Functional Groups, Intermolecular Forces, and Infrared Ir Spectroscopy

An Introduction to Organic Reactions: Acids and Bases

Alkanes: Nomenclature, Conformational Analysis, and an Introduction to Synthesis

Stereochemistry: Chiral Molecules

Ionic Reactions - Nucleophilic Substitution and Elimination Reactions of Alkyl Halides

Alkenes and Alkynes I: Properties and Synthesis, Elimination Reactions of Alkyl Halides

Alkenes and Alkynes Ii: Addition Reactions

Nuclear Magnetic Resonance and Mass Spectrometry: Tools for Structure Determination

Radical Reactions

Alcohols and Ethers

Alcohols From Carbonyl Compounds Oxidation-Reduction and Organometallic Compounds

Conjugated Unsaturated Systems

Reactions of Aromatic Compounds

Aldehydes and Ketones I Nucleophilic Addition to the Carbonyl Group

Aldehydes and Ketones Ii Aldol Reactions

Carboxylic Acids and Their Derivatives Nucleophilic Addition - Elimination at the Acyl Carbon

Synthesis and Reactions of Beta-Dicarbonyl Compounds: More Chemistry of Enolate Ions

Amines

Phenols and Aryl Halides: Nucleophilic Aromatic Substitution

Carbohydrates

Lipids

Amino Acids and Proteins

Nucleic Acids and Protein Synthesis

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

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

In the molecular orbital model of benzene,how many pairs of degenerate $\pi$ -antibonding molecular orbitals are there?

Which isomer of C₇H₇Cl exhibits strong IR absorbances at 690 and 750 cm¹?

Hückel's Rule requires _________ $\pi$ electrons for an aromatic compound.

For which of the following substances,C₉H₁₀O,would the aromatic multiplet,in its ¹H NMR spectrum,consist of two doublets?

Draw all significant resonance structures for pyridine,C₆H₅N

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

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