Question 1

Starting with benzene,the best method for preparing p-nitrobenzoic acid is:

Accepted Answer

A)  HNO3/H2SO4;then CH3Cl/AlCl3;then separation of isomers;then KMnO4/
-OH/heat,followed by H3O+. 
B)  CH3Cl/AlCl3;then HNO3/H2SO4;then separation of isomers;then KMnO4/
-OH/heat,followed by H3O+. 
C)  CH3Cl/AlCl3;then KMnO4/-OH/heat,followed by H3O+;then HNO3/H2SO4. 
D)  HNO3/H2SO4;then KMnO4/-OH/heat,followed by H3O+;then CH3Cl/AlCl3. 
E)  HNO3/H2SO4;then CO2,followed by H3O+. 
A)  HNO3/H2SO4;then CH3Cl/AlCl3;then separation of isomers;then KMnO4/
-OH/heat,followed by H3O+. 
B)  CH3Cl/AlCl3;then HNO3/H2SO4;then separation of isomers;then KMnO4/
-OH/heat,followed by H3O+. 
C)  CH3Cl/AlCl3;then KMnO4/-OH/heat,followed by H3O+;then HNO3/H2SO4. 
D)  HNO3/H2SO4;then KMnO4/-OH/heat,followed by H3O+;then CH3Cl/AlCl3. 
E)  HNO3/H2SO4;then CO2,followed by H3O+.

Question 2

A mixture of chlorobenzene (1 mol)and acetanilide (1mol)is allowed to react with Br2 (0.5 mol)in the presence of trace amounts of FeBr3.What is the principal product of the competing reactions?

Accepted Answer

A)  1-bromo-4-chlorobenzene 
B)  1-bromo-2-chlorobenzene 
C)  1-bromo-3-chlorobenzene 
D)  4-bromoacetanilide 
E)  3-bromoacetanilide 
A)  1-bromo-4-chlorobenzene 
B)  1-bromo-2-chlorobenzene 
C)  1-bromo-3-chlorobenzene 
D)  4-bromoacetanilide 
E)  3-bromoacetanilide

Question 3

The ortho/para product ratio is expected to be the smallest for the bromination of which of these?

Accepted Answer

A)  Toluene 
B)  Isopropylbenzene 
C)  Butylbenzene 
D)  sec-Butylbenzene 
E)  tert-Butylbenzene 
A)  Toluene 
B)  Isopropylbenzene 
C)  Butylbenzene 
D)  sec-Butylbenzene 
E)  tert-Butylbenzene

Question 4

Which of the following contributors to the resonance stabilized hybrid formed when aniline undergoes para-chlorination would be exceptionally stable?

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 5

Which would be the product,X,of the following reaction sequence?

Accepted Answer

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

Question 6

Aryl and vinyl halides cannot be used in the Friedel-Crafts alkylation because they do not __________.

Accepted Answer

form carbo

Question 7

Which of these liquids would be unsuitable as an inert solvent for a Friedel-Crafts reaction?

Accepted Answer

A)  Chlorobenzene 
B)  Nitrobenzene 
C)  Acetophenone 
D)  (Trifluoromethyl)benzene 
E)  All could be used. 
A)  Chlorobenzene 
B)  Nitrobenzene 
C)  Acetophenone 
D)  (Trifluoromethyl)benzene 
E)  All could be used.

Question 8

What would you expect to be the major product obtained from the monobromination of m-dichlorobenzene?

Accepted Answer

A)  I 
B)  II 
C)  III 
D)  Equal amounts of I and II 
E)  Equal amounts of I,II and III 
A)  I 
B)  II 
C)  III 
D)  Equal amounts of I and II 
E)  Equal amounts of I,II and III

Question 9

Which of the following would be the best synthesis of 1,4-dimethyl-2-nitrobenzene?

Accepted Answer

A) 
  
B) 
  
C) 
  
D) 
  
E)  All of these are equally good. 
A) 
  
B) 
  
C) 
  
D) 
  
E)  All of these are equally good.

Question 10

The reaction of benzene with   in the presence of anhydrous aluminum chloride produces principally which of these?

Accepted Answer

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

Question 11

What product would result from the following series of reactions:

Accepted Answer

The answer of What product would result from the following...

Question 12

The compound 4-bromo-1-propylbenzene is best made from benzene by the application of these reagents in the order shown:

Accepted Answer

A)  (1)Br2,Fe (2)CH3CH2CH2Cl,AlCl3 
B)  (1)CH3CH2CH2Cl,AlCl3 (2)Br2,Fe 
C) 
  
D) 
  
E)  (1)(CH3)2CHCl,AlCl3 (2)Br2,Fe 
A)  (1)Br2,Fe (2)CH3CH2CH2Cl,AlCl3 
B)  (1)CH3CH2CH2Cl,AlCl3 (2)Br2,Fe 
C) 
  
D) 
  
E)  (1)(CH3)2CHCl,AlCl3 (2)Br2,Fe

Question 13

Which of the following reactions would produce cumene?

Accepted Answer

A) 
  
B) 
  
C) 
  
D) 
  
E)  All of these 
A) 
  
B) 
  
C) 
  
D) 
  
E)  All of these

Question 14

Using a potential energy diagram,explain/illustrate the preferential formation of the 3 substituted product instead of the 2 product in the electrophilic aromatic substitution of benzo[b] thiophene (shown).

Accepted Answer

3-substitution is preferred,since this l

Question 15

Which of the following is not an ortho-para director in electrophilic aromatic substitution?

Accepted Answer

A)  -CF3 
B)  -OCH3 
C)  -CH3 
D)  -F 
E)  -NH2 
A)  -CF3 
B)  -OCH3 
C)  -CH3 
D)  -F 
E)  -NH2

Question 16

Suggest a reasonable synthetic strategy for the synthesis of 4-methyl-1-phenyl-1-pentanol from 4-methylpentanoyl chloride, (CH3)2CHCH2CH2COCl

Accepted Answer

Question 17

Electron-donating groups increase the electron density on the aromatic ring,causing it to be more reactive than benzene itself towards EAS.These types of groups are called _____________ groups.

Accepted Answer

The answer of Electron-donating groups increase the electron density on...

Question 18

Which of the compounds listed below would you expect to give the greatest amount of meta-product when subjected to ring bromination?

Accepted Answer

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

Question 19

What is a feature found in all ortho-para directing groups?

Accepted Answer

A)  An oxygen atom is directly attached to the aromatic ring. 
B)  The atom attached to the aromatic ring possesses an unshared pair of electrons. 
C)  The group has the ability to delocalize the positive charge of the arenium ion. 
D)  The atom directly attached to the aromatic ring is more electronegative than carbon. 
E)  The group contains a multiple bond. 
A)  An oxygen atom is directly attached to the aromatic ring. 
B)  The atom attached to the aromatic ring possesses an unshared pair of electrons. 
C)  The group has the ability to delocalize the positive charge of the arenium ion. 
D)  The atom directly attached to the aromatic ring is more electronegative than carbon. 
E)  The group contains a multiple bond.

Question 20

Consider the following reaction: what is the expected product?

Accepted Answer

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

Exam 15: Reactions of Aromatic Compounds

Starting with benzene,the best method for preparing p-nitrobenzoic acid is:

A mixture of chlorobenzene (1 mol)and acetanilide (1mol)is allowed to react with Br2 (0.5 mol)in the presence of trace amounts of FeBr3.What is the principal product of the competing reactions?

The ortho/para product ratio is expected to be the smallest for the bromination of which of these?

Which of the following contributors to the resonance stabilized hybrid formed when aniline undergoes para-chlorination would be exceptionally stable?

Which would be the product,X,of the following reaction sequence?

Aryl and vinyl halides cannot be used in the Friedel-Crafts alkylation because they do not __________.

Which of these liquids would be unsuitable as an inert solvent for a Friedel-Crafts reaction?

What would you expect to be the major product obtained from the monobromination of m-dichlorobenzene?

Which of the following would be the best synthesis of 1,4-dimethyl-2-nitrobenzene?

The reaction of benzene with in the presence of anhydrous aluminum chloride produces principally which of these?

What product would result from the following series of reactions:

The compound 4-bromo-1-propylbenzene is best made from benzene by the application of these reagents in the order shown:

Which of the following reactions would produce cumene?

Using a potential energy diagram,explain/illustrate the preferential formation of the 3 substituted product instead of the 2 product in the electrophilic aromatic substitution of benzo[b] thiophene (shown).

Which of the following is not an ortho-para director in electrophilic aromatic substitution?

Suggest a reasonable synthetic strategy for the synthesis of 4-methyl-1-phenyl-1-pentanol from 4-methylpentanoyl chloride, (CH3)2CHCH2CH2COCl

Electron-donating groups increase the electron density on the aromatic ring,causing it to be more reactive than benzene itself towards EAS.These types of groups are called _____________ groups.

Which of the compounds listed below would you expect to give the greatest amount of meta-product when subjected to ring bromination?

What is a feature found in all ortho-para directing groups?

Consider the following reaction: what is the expected product?

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

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

Filters

A mixture of chlorobenzene (1 mol)and acetanilide (1mol)is allowed to react with Br₂ (0.5 mol)in the presence of trace amounts of FeBr₃.What is the principal product of the competing reactions?

Suggest a reasonable synthetic strategy for the synthesis of 4-methyl-1-phenyl-1-pentanol from 4-methylpentanoyl chloride, (CH₃)₂CHCH₂CH₂COCl