Question 1

What is the major product of nitration of thiophene?

Accepted Answer

A) 
  
B) 
  
C) 
  
D) 
  
E)  No reaction occurs. 
A) 
  
B) 
  
C) 
  
D) 
  
E)  No reaction occurs.

Question 2

What is the electrophile in the reaction shown here?

Accepted Answer

A)    
B)  AlCl3 
C)    
D)    
E)  Benzene 
A)    
B)  AlCl3 
C)    
D)    
E)  Benzene

Question 3

Explain why benzene is inert to treatment with hydrogen gas unless special conditions are used.

Accepted Answer

Even though the hydrogenation of benzene

Question 4

Draw a mechanism for the transformation shown here.Include all lone pairs, curved arrows, and
nonzero formal charges.

Accepted Answer

The answer of Draw a mechanism for the transformation shown...

Question 5

Bromination of aniline results in  2,4,6 -tribromoaniline. Which of the following compounds will be mono-brominated in para position upon treatment with   and a Lewis acid catalyst?

Accepted Answer

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

Question 6

Draw the structure of the electrophile in the following reaction.

Accepted Answer

The answer of Draw the structure of the electrophile in...

Question 7

Design a multistep synthesis to produce o-bromoaniline as the sole product using aniline as the
starting material (i.e., you must avoid generating over-brominated products and p-bromoaniline).
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 to produce o-bromoaniline...

Question 8

Which of the following statements is true?

Accepted Answer

A) All meta directors are electron-withdrawing groups. 
B) All electron-withdrawing groups are meta directors. 
C) All ortho, para directors are activating. 
D) All ortho, para directors are deactivating. 
E) All electron-donating groups are meta directors. 
A) All meta directors are electron-withdrawing groups. 
B) All electron-withdrawing groups are meta directors. 
C) All ortho, para directors are activating. 
D) All ortho, para directors are deactivating. 
E) All electron-donating groups are meta directors.

Question 9

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

Accepted Answer

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

Question 10

What is the product of the following reaction?

Accepted Answer

The answer of What is the product of the following...

Question 11

Predict the product of the following reaction and show the product after the first step.

Accepted Answer

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

Question 12

A chemist attempted the following Friedel-Crafts alkylation and did not successfully isolate the intended product:   Explain what product the chemist most likely did isolate and why, and provide an alternate pathway starting from benzene that would provide the intended product.

Accepted Answer

The product most likely isolated would b

Question 13

Which of the following would not react with the compound shown?

Accepted Answer

A)  KI 
B)  CuCN 
C)  CuBr 
D)  HCl 
E)  HBF4 
A)  KI 
B)  CuCN 
C)  CuBr 
D)  HCl 
E)  HBF4

Question 14

Explain why furan undergoes the Diels-Alder reaction, but benzene typically does not.

Accepted Answer

The difference between the reactivity of

Question 15

Predict the product of the following reaction and draw a mechanism to rationalize its formation. Include all necessary lone pairs, curved arrows, and nonzero formal charges.

Accepted Answer

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

Question 16

Which of the following statements about benzyne is false?

Accepted Answer

A)  The geometry around the alkyne is bent. 
B)  There are four hydrogen atoms. 
C)  Each of the two  π because  bonds in the alkyne results from overlap of 2p orbitals on adjacent carbons. 
D)  One of the π bonds is involved in the ring's  π system, while the other is not. 
E)  The compound is strained and highly reactive. 
A)  The geometry around the alkyne is bent. 
B)  There are four hydrogen atoms. 
C)  Each of the two  π because  bonds in the alkyne results from overlap of 2p orbitals on adjacent carbons. 
D)  One of the π bonds is involved in the ring's  π system, while the other is not. 
E)  The compound is strained and highly reactive.

Question 17

Shown below is an electrophilic aromatic substitution reaction. Which of the following statements about this reaction is/are true?
 
I. The products of ortho and para substitution are favored in the overall reaction.
II. The product of meta substitution is favored in the overall reaction.
III. For all three substitution pathways (ortho, meta, and para) the transition state in the rate-limiting step is lower in energy than the transition state for rate-limiting step in the bromination of benzene.
IV. Compared to the energy of the transition state for the rate-limiting step in the bromination of benzene, the transition state in the rate-limiting step for this reaction is lower in energy for the ortho and para pathways, but higher in energy for the meta pathway.

Accepted Answer

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

Question 18

Predict the product of the following reaction.

Accepted Answer

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

Question 19

Phenol usually reacts easily with electrophiles.However, nitration of phenol with nitric acid is unsuccessful since the oxidation of phenol to p-quinone is faster than the electrophilic substitution.   However, the nitration reaction shown below is successful. Explain why the reactivity of starting material is different from that of phenol. Draw the nitration product.

Accepted Answer

@#IMG-DLM& The strong electron-withdrawi

Question 20

Predict the major organic product and draw the structure of the electrophile in the following
reaction.

Accepted Answer

The answer of Predict the major organic product and draw...

Exam 15: Substitution Reactions of Aromatic Compounds

What is the major product of nitration of thiophene?

What is the electrophile in the reaction shown here?

Explain why benzene is inert to treatment with hydrogen gas unless special conditions are used.

Draw a mechanism for the transformation shown here.Include all lone pairs, curved arrows, and nonzero formal charges.

Bromination of aniline results in 2,4,6 -tribromoaniline. Which of the following compounds will be mono-brominated in para position upon treatment with and a Lewis acid catalyst?

Draw the structure of the electrophile in the following reaction.

Which of the following statements is true?

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

What is the product of the following reaction?

Predict the product of the following reaction and show the product after the first step.

A chemist attempted the following Friedel-Crafts alkylation and did not successfully isolate the intended product: Explain what product the chemist most likely did isolate and why, and provide an alternate pathway starting from benzene that would provide the intended product.

Which of the following would not react with the compound shown?

Explain why furan undergoes the Diels-Alder reaction, but benzene typically does not.

Predict the product of the following reaction and draw a mechanism to rationalize its formation. Include all necessary lone pairs, curved arrows, and nonzero formal charges.

Which of the following statements about benzyne is false?

Predict the product of the following reaction.

Predict the major organic product and draw the structure of the electrophile in 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

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