Question 1

Consider the reaction below to answer the following question(s).  
-Refer to instructions. The nucleophile in the reaction is indicated by letter _____.

Accepted Answer

A) A 
B) B 
C) C 
D) D 
A) A 
B) B 
C) C 
D) D A

Question 2

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

Accepted Answer

A) 
  
B) 
  
C) 
  
D) 
  
A) 
  
B) 
  
C) 
  
D) 
  B

Question 3

Consider the following compound:   a)Provide the correct IUPAC name for the compound.
b)Draw and name the other isomeric nitrotoluenes.

Accepted Answer

a)
m-nitrotoluene or 1-methyl-3-nitrobenzene
b)p-nitrotoluene
o-nitrotoluene
1,4-nitrotoluene
1,2-nitrotoluene

Question 4

Consider the reaction below to answer the following question(s).  
-Refer to instructions. The Lewis acid catalyst in the reaction is indicated by letter _____.

Accepted Answer

A) A 
B) B 
C) C 
D) D 
A) A 
B) B 
C) C 
D) D

Question 5

Which of the following undergoes the most rapid bromination upon treatment with Br2/FeBr3?

Accepted Answer

A)  benzene 
B)  nitrobenzene 
C)  bromobenzene 
D)  benzaldehyde 
A)  benzene 
B)  nitrobenzene 
C)  bromobenzene 
D)  benzaldehyde

Question 6

What is the electrophile in the reaction of benzene with acetyl chloride, CH3COCl, and AlCl3?

Accepted Answer

A)  CH3C
O+ 
B)  CH3+ 
C)  CH3CO2− 
D)  benzene 
A)  CH3C
O+ 
B)  CH3+ 
C)  CH3CO2− 
D)  benzene

Question 7

Consider the production of 1-bromo-4-nitrobenzene:   a)Explain why Pathway A for the production of 1-bromo-4-nitrobenzene produces a higher yield of the product.
b)If reaction Pathway A is carried out at high temperatures, a trisubstituted product forms. Draw the structure of the product and explain why it forms.

Accepted Answer

a)
Bromine is an o/p-director while the

Question 8

What is the major organic product obtained from the following sequence of reactions?

Accepted Answer

A) 
  
B) 
  
C) 
  
D) 
  
A) 
  
B) 
  
C) 
  
D)

Question 9

Circle the compound(s) in the following set that will undergo both substitution and addition when treated with Br2.

Accepted Answer

Question 10

What is the IUPAC name of the following compound?

Accepted Answer

A)  3-bromo-4-nitrobenzaldehyde 
B)  2-bromo-1-nitro-4-benzoic acid 
C)  3-bromo-4-nitroacetophenone 
D)  3-bromo-4-nitrobenzoic acid 
A)  3-bromo-4-nitrobenzaldehyde 
B)  2-bromo-1-nitro-4-benzoic acid 
C)  3-bromo-4-nitroacetophenone 
D)  3-bromo-4-nitrobenzoic acid

Question 11

Which of the following heterocycles is aromatic?

Accepted Answer

A) 
  
B) 
  
C) 
  
D) 
  
A) 
  
B) 
  
C) 
  
D)

Question 12

Which of the following statements is true about the structure of benzene?

Accepted Answer

A)  six atomic 2p orbitals interact to form six π molecular orbitals 
B)  there are three bonding π molecular orbitals and three π antibonding molecular orbitals 
C)  the ground state electronic configuration of benzene has six electrons in three π bonding molecular orbitals 
D)  the carbon−carbon bonds are all the same length 
E)  All of these 
A)  six atomic 2p orbitals interact to form six π molecular orbitals 
B)  there are three bonding π molecular orbitals and three π antibonding molecular orbitals 
C)  the ground state electronic configuration of benzene has six electrons in three π bonding molecular orbitals 
D)  the carbon−carbon bonds are all the same length 
E)  All of these

Question 13

An accurate description of the structure of benzene is:

Accepted Answer

A)  The π bonds are quickly moving around the ring. 
B)  There are two distinct structures that are in equilibrium. 
C)  All the carbon−carbon bonds are equal in length. 
D)  There are distinct single and double bonds. 
E)  Some bonds are longer than others. 
A)  The π bonds are quickly moving around the ring. 
B)  There are two distinct structures that are in equilibrium. 
C)  All the carbon−carbon bonds are equal in length. 
D)  There are distinct single and double bonds. 
E)  Some bonds are longer than others.

Question 14

How many π electrons are present in the following heterocycle?

Accepted Answer

A)  2 
B)  4 
C)  6 
D)  8 
E)  10 
A)  2 
B)  4 
C)  6 
D)  8 
E)  10

Question 15

Which of the following sets of substituents are all deactivating groups in electrophilic aromatic substitution reactions?

Accepted Answer

A)  Cl, CN, NO2 
B)  Cl, NH2, CH3 
C)  CH3, OCH3, COCH3 
D)  CH3, NH2, OCH3 
A)  Cl, CN, NO2 
B)  Cl, NH2, CH3 
C)  CH3, OCH3, COCH3 
D)  CH3, NH2, OCH3

Question 16

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

Accepted Answer

A) 
 
​ 
B) 
 
​ 
C) 
 
​ 
D) 
 
​ 
A) 
 
​ 
B) 
 
​ 
C) 
 
​ 
D) 
 
​

Question 17

Place the following in order of reactivity towards electrophilic aromatic substitution.

Accepted Answer

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

Question 18

What is the IUPAC name of the following compound?

Accepted Answer

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

Question 19

Predict the major product of each of the following reactions.

Accepted Answer

The answer of Predict the major product of each of...

Question 20

Consider the reaction below to answer the following question(s).  
-Refer to instructions. This reaction proceeds _____________ (faster or slower) than benzene.

Accepted Answer

The answer of Consider the reaction below to answer the...

Exam 9: Aromatic Compounds

Consider the reaction below to answer the following question(s). -Refer to instructions. The nucleophile in the reaction is indicated by letter _____.

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

Consider the following compound: a)Provide the correct IUPAC name for the compound. b)Draw and name the other isomeric nitrotoluenes.

Consider the reaction below to answer the following question(s). -Refer to instructions. The Lewis acid catalyst in the reaction is indicated by letter _____.

Which of the following undergoes the most rapid bromination upon treatment with Br2/FeBr3?

What is the electrophile in the reaction of benzene with acetyl chloride, CH3COCl, and AlCl3?

What is the major organic product obtained from the following sequence of reactions?

Circle the compound(s) in the following set that will undergo both substitution and addition when treated with Br2.

What is the IUPAC name of the following compound?

Which of the following heterocycles is aromatic?

Which of the following statements is true about the structure of benzene?

An accurate description of the structure of benzene is:

How many π electrons are present in the following heterocycle?

Which of the following sets of substituents are all deactivating groups in electrophilic aromatic substitution reactions?

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

Place the following in order of reactivity towards electrophilic aromatic substitution.

What is the IUPAC name of the following compound?

Predict the major product of each of the following reactions.

Consider the reaction below to answer the following question(s). -Refer to instructions. This reaction proceeds _____________ (faster or slower) than benzene.

Structure and Bonding

Polar Covalent Bonds; Acids and Bases

Organic Compounds: Alkanes and Their Stereochemistry

Organic Compounds: Cycloalkanes and Their Stereochemistry

Stereochemistry at Tetrahedral Centers

An Overview of Organic Reactions

Alkenes and Alkynes

Reactions of Alkenes and Alkynes

Structure Determination: Mass Spectrometry, Infrared Spectroscopy, and Ultraviolet Spectroscopy

Structure Determination: Mass Spectrometry, Infrared Spectroscopy, and Ultraviolet Spectroscopy

Structure Determination: Nuclear Magnetic Resonance Spectroscopy

Organohalides: Nucleophilic Substitutions and Eliminations

Alcohols, Phenols, and Thiols; Ethers and Sulfides

Aldehydes and Ketones: Nucleophilic Addition Reactions

Carboxylic Acids and Nitriles

Carboxylic Acid Derivatives: Nucleophilic Acyl Substitution Reactions

Carbonyl Alpha-Substitution and Condensation Reactions

Amines and Heterocycles

Biomolecules: Amino Acids, Peptides, and Proteins

Amino Acid Metabolism

Biomolecules: Carbohydrates

Carbohydrate Metabolism

Biomolecules: Lipids and Their Metabolism

Biomolecules: Nucleic Acids and Their Metabolism

Orbitals and Organic Chemistry: Pericyclic Reactionse

Synthetic Polymerse

Filters

Which of the following undergoes the most rapid bromination upon treatment with Br₂/FeBr₃?

What is the electrophile in the reaction of benzene with acetyl chloride, CH₃COCl, and AlCl₃?

Circle the compound(s) in the following set that will undergo both substitution and addition when treated with Br₂.

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