Question 1

Predict the product of the following reaction.

Accepted Answer

The answer of Predict the product of the following reaction....

Question 2

Which of the following compounds will undergo nucleophilic aromatic substitution with methoxide ion at the fastest rate?

Accepted Answer

A)  
  
B) 1
  
C) 
  
D) 
  
E) 
  
A)  
  
B) 1
  
C) 
  
D) 
  
E)

Question 3

Design a multistep synthesis for the following transformation.You may use any organic or inorganic reagents.Show the reagents needed for each step and the product of each step.

Accepted Answer

The answer of Design a multistep synthesis for the following...

Question 4

Benzene is subjected to an electrophilic aromatic substitution reaction, yielding a single product. This product is then subjected to the same reaction again.The reaction is successful, though slower than the first, and two products result.One of these, product A, has two signals in the aromatic region of the 1H NMR spectrum, while the other, product B, has only one signal.Propose possible structures for A and B.

Accepted Answer

The two products must be the result of o

Question 5

Aniline is more activating towards electrophilic aromatic substitution than phenol.Explain.

Accepted Answer

The oxygen atom in phenol is m

Question 6

Which of the following statements about the reaction shown here is true?

Accepted Answer

A)  The ortho and para pathways are disfavored because of steric hindrance. 
B)  Sulfuric acid and nitric acid in combination direct groups to the meta position on the ring. 
C)  The intermediate for the ortho and para pathways has positive and partial positive charges on adjacent atoms whereas the meta pathway intermediate does not. 
D)  Reaction produces benzoic action. 
E)  The reaction is a Friedel-Crafts acylation. 
A)  The ortho and para pathways are disfavored because of steric hindrance. 
B)  Sulfuric acid and nitric acid in combination direct groups to the meta position on the ring. 
C)  The intermediate for the ortho and para pathways has positive and partial positive charges on adjacent atoms whereas the meta pathway intermediate does not. 
D)  Reaction produces benzoic action. 
E)  The reaction is a Friedel-Crafts acylation.

Question 7

Design a synthesis of the target molecule shown from benzene and any organic or inorganic
reagents.Show the reagents needed for each step and the product of each step.

Accepted Answer

The answer of Design a synthesis of the target molecule...

Question 8

What is the proper description of the compound shown here?

Accepted Answer

A)  diazonium salt 
B)  nitroso compound 
C)  aniline 
D)  anilinium ion 
E)  diazotic acid 
A)  diazonium salt 
B)  nitroso compound 
C)  aniline 
D)  anilinium ion 
E)  diazotic acid

Question 9

Draw the energy diagram for the following reaction.

Accepted Answer

The answer of Draw the energy diagram for the following...

Question 10

What is the electrophile in this reaction?

Accepted Answer

A)  HNO3 
B)  H2SO4 
C)  SO3 
D)  NO2+ 
E)  Benzene 
A)  HNO3 
B)  H2SO4 
C)  SO3 
D)  NO2+ 
E)  Benzene

Question 11

Which of the following compounds is the major product of this reaction?

Accepted Answer

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

Question 12

What is the electrophile in this reaction?

Accepted Answer

A)  H2SO4 
B)  SO3 
C)  HSO3+ 
D)  Benzene 
E)  HSO4- 
A)  H2SO4 
B)  SO3 
C)  HSO3+ 
D)  Benzene 
E)  HSO4-

Question 13

Which conditions would you use to accomplish the following transformation?

Accepted Answer

A)  HNO3/H2SO4 
B) KOH, H2NNH2, ethylene glycol 
C) HNO3/ H2SO4, then H2/Pd/C 
D) HNO3/H2SO4, then H2O 
E)  Na, NH3 
A)  HNO3/H2SO4 
B) KOH, H2NNH2, ethylene glycol 
C) HNO3/ H2SO4, then H2/Pd/C 
D) HNO3/H2SO4, then H2O 
E)  Na, NH3

Question 14

Why is one equivalent of  AlCl3  required for the transformation shown here?

Accepted Answer

A)  Either the oxygen or the chlorine in the acyl chloride can attach to the  Al  atom in  AlCl3. 
B)  AlCl3  is needed to produce the acyl chloride during the course of the reaction. 
C)  The product forms a complex with the AlCl3. 
D)  The product would rearrange unless there were extra. AlCl3  present. 
E)  Both benzene and the acyl chloride form complexes with the AlCl3. 
A)  Either the oxygen or the chlorine in the acyl chloride can attach to the  Al  atom in  AlCl3. 
B)  AlCl3  is needed to produce the acyl chloride during the course of the reaction. 
C)  The product forms a complex with the AlCl3. 
D)  The product would rearrange unless there were extra. AlCl3  present. 
E)  Both benzene and the acyl chloride form complexes with the AlCl3.

Question 15

Which of the following substrates would not provide a rearranged product when reacted with benzene in a Friedel-Crafts alkylation reaction?

Accepted Answer

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

Question 16

Which of the following compounds is deactivated in electrophilic aromatic substitution reaction relative to benzene?

Accepted Answer

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

Question 17

Which of the following compounds is the major product of this reaction?

Accepted Answer

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

Question 18

Predict the product of the following reaction.

Accepted Answer

The answer of Predict the product of the following reaction....

Question 19

Design a multistep synthesis for the following transformation.You may use any organic or
inorganic reagents.Show the reagents needed for each step and the product of each step.

Accepted Answer

The answer of Design a multistep synthesis for the following...

Question 20

Predict the product of the following reaction.

Accepted Answer

The answer of Predict the product of the following reaction....

Exam 15: Substitution Reactions of Aromatic Compounds

Predict the product of the following reaction.

Which of the following compounds will undergo nucleophilic aromatic substitution with methoxide ion at the fastest rate?

Design a multistep synthesis for the following transformation.You may use any organic or inorganic reagents.Show the reagents needed for each step and the product of each step.

Aniline is more activating towards electrophilic aromatic substitution than phenol.Explain.

Which of the following statements about the reaction shown here is true?

Design a synthesis of the target molecule shown from benzene and any organic or inorganic reagents.Show the reagents needed for each step and the product of each step.

What is the proper description of the compound shown here?

Draw the energy diagram for the following reaction.

What is the electrophile in this reaction?

Which of the following compounds is the major product of this reaction?

What is the electrophile in this reaction?

Which conditions would you use to accomplish the following transformation?

Why is one equivalent of AlCl3 required for the transformation shown here?

Which of the following substrates would not provide a rearranged product when reacted with benzene in a Friedel-Crafts alkylation reaction?

Which of the following compounds is deactivated in electrophilic aromatic substitution reaction relative to benzene?

Which of the following compounds is the major product of this reaction?

Predict the product of the following reaction.

Design a multistep synthesis for the following transformation.You may use any organic or inorganic reagents.Show the reagents needed for each step and the product of each step.

Predict the product of the following reaction.

Atoms and Molecules; Orbitals and Bonding

Alkanes

Alkenes and Alkynes

Stereochemistry

Rings

Substituted Alkanes: Alkyl Halides, Alcohols, Amines, Ethers,thiols, and Thioethers

Substitution Reactions: the Sn2 and Sn1 Reactions

Elimination Reactions: the E1 and E2 Reactions

Analytical Chemistry: Spectroscopy

Electrophilic Additions to Alkenes

More Additions to Bonds

Radical Reactions

Dienes and the Allyl System: 2p Orbitals in Conjugation

Aromaticity

Carbonyl Chemistry 1: Addition Reactions

Carboxylic Acids

Derivatives of Carboxylic Acids: Acyl Compounds

Carbonyl Chemistry 2: Reactions at the Α Position

Special Topic: Carbohydrates

Special Topic: Bio-Organic Chemistry

Special Topic: Amino Acids and Polyamino Acids Peptides and Proteins

Special Topic: Reactions Controlled by Orbital Symmetry

Special Topic: Intramolecular Reactions and Neighboring Group Participation

Filters

Why is one equivalent of AlCl₃ required for the transformation shown here?