Question 1

Which of the following compound has the highest melting point?

Accepted Answer

A)  benzene 
B)  toluene 
C)  o-dichlorobenzene 
D)  m-dichlorobenzene 
E)  p-dichlorobenzene 
A)  benzene 
B)  toluene 
C)  o-dichlorobenzene 
D)  m-dichlorobenzene 
E)  p-dichlorobenzene

Question 2

Is the molecule below aromatic, antiaromatic, or nonaromatic?

Accepted Answer

The answer of Is the molecule below aromatic, antiaromatic, or...

Question 3

3-Chlorocyclopropene is solvolyzed in methanol at a much higher rate than is chlorocyclopropane. Offer an explanation.

Accepted Answer

Cyclopropenyl cation, the carb

Question 4

Which of the following is another name for cyclobutadiene?

Accepted Answer

A)  [2]annulene 
B)  [4]annulene 
C)  [6]annulene 
D)  Dewar benzene 
E)  antibenzene 
A)  [2]annulene 
B)  [4]annulene 
C)  [6]annulene 
D)  Dewar benzene 
E)  antibenzene

Question 5

Classify the compound below as aromatic, antiaromatic, or nonaromatic. Assume planarity of the π network.

Accepted Answer

The answer of Classify the compound below as aromatic, antiaromatic,...

Question 6

Which of the following undergoes solvolysis in methanol most rapidly?

Accepted Answer

A)  PhCH2Br 
B)  Ph3CBr 
C)  PhCH2CH2Br 
D)  PhBr 
E)  PhCH2CH2CH2Br 
A)  PhCH2Br 
B)  Ph3CBr 
C)  PhCH2CH2Br 
D)  PhBr 
E)  PhCH2CH2CH2Br

Question 7

How many distinct nodal planes which are perpendicular to the molecular plane are present in the π4* orbital of benzene?

Accepted Answer

A)  0 
B)  1 
C)  2 
D)  4 
E)  5 
A)  0 
B)  1 
C)  2 
D)  4 
E)  5

Question 8

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

Accepted Answer

A)  The structure must be cyclic for aromatic but not antiaromatic compounds? 
B)  Antiaromatic compounds have at least one sp3 hybridized atom in the ring 
C)  Antiaromatic compounds can assume a chair-like structure while aromatic compounds are nearly flat 
D)  Aromatic compounds cannot have a charged atom in the structure 
E)  Only aromatic compounds follow Huckle's rule. 
A)  The structure must be cyclic for aromatic but not antiaromatic compounds? 
B)  Antiaromatic compounds have at least one sp3 hybridized atom in the ring 
C)  Antiaromatic compounds can assume a chair-like structure while aromatic compounds are nearly flat 
D)  Aromatic compounds cannot have a charged atom in the structure 
E)  Only aromatic compounds follow Huckle's rule.

Question 9

Which sequence ranks the indicated protons in order of increasing acidity?

Accepted Answer

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

Question 10

________ is similar to furan, with a sulfur atom in place of the oxygen.

Accepted Answer

The answer of ________ is similar to furan, with a...

Question 11

In the mass spectrum of isobutylbenzene, the base peak occurs at m/z ________.

Accepted Answer

A)  134 
B)  133 
C)  119 
D)  105 
E)  91 
A)  134 
B)  133 
C)  119 
D)  105 
E)  91

Question 12

Why does benzene undergo a substitution reaction with Br2 while cyclohexene undergoes an addition reaction.

Accepted Answer

Addition of Br₂ to benzene is h

Question 13

Provide the name of the compound shown below.

Accepted Answer

m-iodobenz

Question 14

Which of the following undergoes SN2 reaction with sodium methoxide most rapidly?

Accepted Answer

A)  PhCH2Br 
B)  Ph3CBr 
C)  PhCH2CH2Br 
D)  PhBr 
E)  PhCH2CH2CH2Br 
A)  PhCH2Br 
B)  Ph3CBr 
C)  PhCH2CH2Br 
D)  PhBr 
E)  PhCH2CH2CH2Br

Question 15

Which is more stable, cyclobutadiene or 1,3-butadiene? Explain.

Accepted Answer

1,3-Butadiene is more stable.

Question 16

Provide the structure of p-aminobenzoic acid.

Accepted Answer

The answer of Provide the structure of p-aminobenzoic acid....

Question 17

Is the molecule below aromatic, antiaromatic, or nonaromatic?

Accepted Answer

The answer of Is the molecule below aromatic, antiaromatic, or...

Question 18

How many peaks are in the proton spin decoupled 13C NMR spectrum of 1,2,3-trichlorobenzene?

Accepted Answer

A)  1 
B)  2 
C)  3 
D)  4 
E)  6 
A)  1 
B)  2 
C)  3 
D)  4 
E)  6

Question 19

Provide a correct common name for the following compound.

Accepted Answer

p-acetylbe

Question 20

Which of the following is another accepted name for methyl phenyl ketone?

Accepted Answer

A)  anisole 
B)  cresol 
C)  acetophenone 
D)  benzophenone 
E)  cresone 
A)  anisole 
B)  cresol 
C)  acetophenone 
D)  benzophenone 
E)  cresone

Exam 16: Aromatic Compounds

Which of the following compound has the highest melting point?

Is the molecule below aromatic, antiaromatic, or nonaromatic?

3-Chlorocyclopropene is solvolyzed in methanol at a much higher rate than is chlorocyclopropane. Offer an explanation.

Which of the following is another name for cyclobutadiene?

Classify the compound below as aromatic, antiaromatic, or nonaromatic. Assume planarity of the π network.

Which of the following undergoes solvolysis in methanol most rapidly?

How many distinct nodal planes which are perpendicular to the molecular plane are present in the π4* orbital of benzene?

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

Which sequence ranks the indicated protons in order of increasing acidity?

________ is similar to furan, with a sulfur atom in place of the oxygen.

In the mass spectrum of isobutylbenzene, the base peak occurs at m/z ________.

Why does benzene undergo a substitution reaction with Br2 while cyclohexene undergoes an addition reaction.

Provide the name of the compound shown below.

Which of the following undergoes SN2 reaction with sodium methoxide most rapidly?

Which is more stable, cyclobutadiene or 1,3-butadiene? Explain.

Provide the structure of p-aminobenzoic acid.

Is the molecule below aromatic, antiaromatic, or nonaromatic?

How many peaks are in the proton spin decoupled 13C NMR spectrum of 1,2,3-trichlorobenzene?

Provide a correct common name for the following compound.

Which of the following is another accepted name for methyl phenyl ketone?

Introduction and Review

Structure and Properties of Organic Molecules

Structure and Stereochemistry of Alkanes

The Study of Chemical Reactions

Stereochemistry

Alkyl Halides: Nucleophilic Substitution and Elimination

Structure and Synthesis of Alkenes

Reactions of Alkenes

Alkynes

Structure and Synthesis of Alcohols

Reactions of Alcohols

Infrared Spectroscopy and Mass Spectrometry

Nuclear Magnetic Resonance Spectroscopy

Ethers, Epoxides, and Thioethers

Conjugated Systems, Orbital Symmetry, and Ultraviolet Spectroscopy

Reactions of Aromatic Compounds

Ketones and Aldehydes

Amines

Carboxylic Acids

Carboxylic Acid Derivatives

Condensations and Alpha Substitutions of Carboxyl Compounds

Carbohydrates and Nucleic Acids

Amino Acids, Peptides, and Proteins

Lipids

Synthetic Polymers

Filters

How many distinct nodal planes which are perpendicular to the molecular plane are present in the π₄^* orbital of benzene?

Why does benzene undergo a substitution reaction with Br₂ while cyclohexene undergoes an addition reaction.

Which of the following undergoes S_N2 reaction with sodium methoxide most rapidly?

How many peaks are in the proton spin decoupled ¹³C NMR spectrum of 1,2,3-trichlorobenzene?