Question 1

In electrophilic aromatic substitution,the attacking species (the electrophile)necessarily is a:

Accepted Answer

A)  neutral species. 
B)  positively charged species. 
C)  lewis acid. 
D)  proton. 
E)  carbocation. 
A)  neutral species. 
B)  positively charged species. 
C)  lewis acid. 
D)  proton. 
E)  carbocation.

Question 2

What would you expect to be the major product obtained from the following reaction?

Accepted Answer

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

Question 3

The major product(s),C,of the following reaction,   would be:

Accepted Answer

A)  I 
B)  II 
C)  III 
D)  Approximately equal amounts of I and II 
E)  Approximately equal amounts of I and III 
A)  I 
B)  II 
C)  III 
D)  Approximately equal amounts of I and II 
E)  Approximately equal amounts of I and III

Question 4

Which is the best sequence of reactions for the preparation of p-bromostyrene from ethylbenzene?

Accepted Answer

A) 
  
B) 
  
C) 
  
D) 
  
E)  None of these syntheses is satisfactory. 
A) 
  
B) 
  
C) 
  
D) 
  
E)  None of these syntheses is satisfactory.

Question 5

What would you expect to be the major product obtained from the following reaction?

Accepted Answer

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

Question 6

What feature is common to all meta-directing groups?

Accepted Answer

A)  The atom directly attached to the ring has a full or well-developed partial positive charge. 
B)  The atom directly attached to the ring is doubly bonded to oxygen. 
C)  One or more halogen atoms are present in the group. 
D)  One or more oxygen atoms are present in the group. 
E)  The group is attached to the ring through a carbon atom. 
A)  The atom directly attached to the ring has a full or well-developed partial positive charge. 
B)  The atom directly attached to the ring is doubly bonded to oxygen. 
C)  One or more halogen atoms are present in the group. 
D)  One or more oxygen atoms are present in the group. 
E)  The group is attached to the ring through a carbon atom.

Question 7

What product would result from the following series of reactions,

Accepted Answer

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

Question 8

Using a potential energy diagram,explain/illustrate the preferential formation of the 2 substituted product instead of the 3 product in the electrophilic aromatic substitution of thiophene.

Accepted Answer

The 2 substitution product is favored si

Question 9

Which of these is a satisfactory synthesis of 1-chloro-2-phenylethane?

Accepted Answer

A)  C6H5CH2CH3 + Cl2,Fe --$\rightarrow$ 
B)  C6H5CH2CH3 + Cl2,400$\degree$C --$\rightarrow$ 
C)  C6H5CH2CH2OH + PCl5 --$\rightarrow$ 
D)  C6H5CH=CH2 + HCl,peroxide --$\rightarrow$ 
E)  C6H6 + CH3CH2Cl,AlCl3 --$\rightarrow$ 
A)  C6H5CH2CH3 + Cl2,Fe --$\rightarrow$ 
B)  C6H5CH2CH3 + Cl2,400$\degree$C --$\rightarrow$ 
C)  C6H5CH2CH2OH + PCl5 --$\rightarrow$ 
D)  C6H5CH=CH2 + HCl,peroxide --$\rightarrow$ 
E)  C6H6 + CH3CH2Cl,AlCl3 --$\rightarrow$

Question 10

Benzoic acid can be prepared by the oxidation of all of the following compounds except this one:

Accepted Answer

A)  C6H5CH=CH2 
B)  C6H5C$ \equiv$CH 
C)  C6H5COCH3 
D)  C6H5CH2CH2CH3 
E)  C6H5C(CH3)3 
A)  C6H5CH=CH2 
B)  C6H5C$ \equiv$CH 
C)  C6H5COCH3 
D)  C6H5CH2CH2CH3 
E)  C6H5C(CH3)3

Question 11

Which would be the product 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 12

Which of these is the rate-determining step in the nitration of benzene?

Accepted Answer

A)  Protonation of nitric acid by sulfuric acid 
B)  Protonation of sulfuric acid by nitric acid 
C)  Loss of a water molecule by the protonated species to produce the nitronium ion 
D)  Addition of the nitronium to benzene to produce the arenium ion 
E)  Loss of a proton by the arenium ion to form nitrobenzene 
A)  Protonation of nitric acid by sulfuric acid 
B)  Protonation of sulfuric acid by nitric acid 
C)  Loss of a water molecule by the protonated species to produce the nitronium ion 
D)  Addition of the nitronium to benzene to produce the arenium ion 
E)  Loss of a proton by the arenium ion to form nitrobenzene

Question 13

Which reagent(s)would you use to carry out the following transformation? ethylbenzene --$\rightarrow$ 2- and 4-chloro-1-ethylbenzene

Accepted Answer

A)  Cl2,light,and heat 
B)  Cl2,FeCl3 
C)  SOCl2 
D)  C2H5Cl,AlCl3 
E)  None of these 
A)  Cl2,light,and heat 
B)  Cl2,FeCl3 
C)  SOCl2 
D)  C2H5Cl,AlCl3 
E)  None of these

Question 14

What would you expect to be the major product obtained from the following reaction?

Accepted Answer

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

Question 15

What would you expect to be the major product obtained from the following reaction?

Accepted Answer

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

Question 16

When toluene is reacted in turn with 1)Cl2 (large excess),heat,and light and 2)Br2,FeBr3,the chief product is:

Accepted Answer

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

Question 17

Which is the best prediction of the site(s)of substitution when 3-methylphenol is nitrated?

Accepted Answer

A)  C-2 
B)  C-4 
C)  C-5 
D)  C-6 
E)  C-4 and C-6 
A)  C-2 
B)  C-4 
C)  C-5 
D)  C-6 
E)  C-4 and C-6

Question 18

Each of the five disubstituted benzenes shown below is nitrated.In which of these cases does the arrow not indicate the chief position of nitration.

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 would you expect to be the major product obtained from the following reaction?

Accepted Answer

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

Question 20

Using a potential energy diagram,explain/illustrate the preferential formation of the 1 nitrated product instead of the 2 nitrated product in the electrophilic aromatic nitration of naphthalene.

Accepted Answer

The 1 substitution product is favored si

Exam 15: Reactions of Aromatic Compounds

In electrophilic aromatic substitution,the attacking species (the electrophile)necessarily is a:

What would you expect to be the major product obtained from the following reaction?

The major product(s),C,of the following reaction, would be:

Which is the best sequence of reactions for the preparation of p-bromostyrene from ethylbenzene?

What would you expect to be the major product obtained from the following reaction?

What feature is common to all meta-directing groups?

What product would result from the following series of reactions,

Using a potential energy diagram,explain/illustrate the preferential formation of the 2 substituted product instead of the 3 product in the electrophilic aromatic substitution of thiophene.

Which of these is a satisfactory synthesis of 1-chloro-2-phenylethane?

Benzoic acid can be prepared by the oxidation of all of the following compounds except this one:

Which would be the product of the following reaction sequence?

Which of these is the rate-determining step in the nitration of benzene?

Which reagent(s)would you use to carry out the following transformation? ethylbenzene -- →\rightarrow→ 2- and 4-chloro-1-ethylbenzene

What would you expect to be the major product obtained from the following reaction?

What would you expect to be the major product obtained from the following reaction?

When toluene is reacted in turn with 1)Cl2 (large excess),heat,and light and 2)Br2,FeBr3,the chief product is:

Which is the best prediction of the site(s)of substitution when 3-methylphenol is nitrated?

Each of the five disubstituted benzenes shown below is nitrated.In which of these cases does the arrow not indicate the chief position of nitration.

What would you expect to be the major product obtained from the following reaction?

Using a potential energy diagram,explain/illustrate the preferential formation of the 1 nitrated product instead of the 2 nitrated product in the electrophilic aromatic nitration of naphthalene.

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

Which reagent(s)would you use to carry out the following transformation? ethylbenzene -- $\rightarrow$ 2- and 4-chloro-1-ethylbenzene

When toluene is reacted in turn with 1)Cl₂ (large excess),heat,and light and 2)Br₂,FeBr₃,the chief product is: