Question 1

Which of the following reactions would yield isopropylbenzene as the major product?

Accepted Answer

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

Question 2

Which is the best sequence of reactions for the following transformation?

Accepted Answer

A)  i)HNO3,H2SO4;ii)CH3MgBr,Et2O;iii)H3O+,heat 
B)  i)CH3MgBr,Et2O;ii)H3O+,heat;iii)HNO3,H2SO4 
C)  i)HNO3,H2SO4;ii)NaBH4,H2O;iii)H3O+,heat 
D)  i)HNO3,H2SO4;ii)LiAlH4,H2O;iii)H3O+,heat 
E)  None of these syntheses is satisfactory. 
A)  i)HNO3,H2SO4;ii)CH3MgBr,Et2O;iii)H3O+,heat 
B)  i)CH3MgBr,Et2O;ii)H3O+,heat;iii)HNO3,H2SO4 
C)  i)HNO3,H2SO4;ii)NaBH4,H2O;iii)H3O+,heat 
D)  i)HNO3,H2SO4;ii)LiAlH4,H2O;iii)H3O+,heat 
E)  None of these syntheses is satisfactory.

Question 3

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

Accepted Answer

A)  C6H5CH2CH3 + Br2,Fe3+ --$\rightarrow$ 
B)  C6H5CH2CH3 + Br2,400 $\degree$C --$\rightarrow$ 
C)  C6H5CH2CH2OH + Br2,CCl4 --$\rightarrow$ 
D)  C6H5CH=CH2 + HBr,ROOR --$\rightarrow$ 
E)  C6H5CH2CH3 + NBS,ROOR --$\rightarrow$ 
A)  C6H5CH2CH3 + Br2,Fe3+ --$\rightarrow$ 
B)  C6H5CH2CH3 + Br2,400 $\degree$C --$\rightarrow$ 
C)  C6H5CH2CH2OH + Br2,CCl4 --$\rightarrow$ 
D)  C6H5CH=CH2 + HBr,ROOR --$\rightarrow$ 
E)  C6H5CH2CH3 + NBS,ROOR --$\rightarrow$

Question 4

Which reagent(s)would you use to carry out the following transformation? ethylbenzene--$\rightarrow$ benzoic acid

Accepted Answer

A)  Cl2,light,and heat 
B)  Cl2,FeCl3 
C)  KMnO4,OH-,heat (then H3O+) 
D)  HNO3/H2SO4 
E)  SO3/H2SO4 
A)  Cl2,light,and heat 
B)  Cl2,FeCl3 
C)  KMnO4,OH-,heat (then H3O+) 
D)  HNO3/H2SO4 
E)  SO3/H2SO4

Question 5

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 pyrrole.

Accepted Answer

The 2 substitution product is favored si

Question 6

When the following substance is treated with Br2/FeBr3,the major product is obtained in good yield,and only very small amounts of minor products are found.What is this major product and why are the minor products not formed to any significant degree? Explain clearly.

Accepted Answer

The major products are produced by bromi

Question 7

Which of the following compounds would be least reactive toward electrophilic substitution?

Accepted Answer

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

Question 8

Undesired polysubstitution of an aromatic nucleus is most likely to be encountered in the case of:

Accepted Answer

A)  Friedel-Crafts alkylation 
B)  Friedel-Crafts acylation 
C)  Nitration 
D)  Sulfonation 
E)  Chlorination 
A)  Friedel-Crafts alkylation 
B)  Friedel-Crafts acylation 
C)  Nitration 
D)  Sulfonation 
E)  Chlorination

Question 9

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 10

How might the following synthesis be carried out:

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 11

Based on your knowledge of electrophilic aromatic substitution,predict the preferential position of attack of an electrophile on thiophene,i.e. ,does the electrophile E+ attack carbon 2,or 3? Explain your answer.   Which substitution product forms preferentially and why?

Accepted Answer

The 2 substitution product is favored si

Question 12

What product would result from the following series of reactions,

Accepted Answer

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

Question 13

Which of the following reactions could be used to synthesize tert-butylbenzene?

Accepted Answer

A) 
  
B) 
  
C) 
  
D)  All of the above 
E)  None of the above 
A) 
  
B) 
  
C) 
  
D)  All of the above 
E)  None of the above

Question 14

Which of the following structures would not be a contributor to the resonance hybrid of the benzyl cation?

Accepted Answer

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

Question 15

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

Accepted Answer

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

Question 16

Based on your knowledge of electrophilic aromatic substitution,and assuming the furan ring of benzo[b]furan (shown)is activated toward electrophilic aromatic substituted more so than the benzenoid ring,predict the preferential position of attack of an electrophile,i.e. ,does the electrophile E+ attack carbon 2,or 3? Explain your answer.   Which substitution product forms preferentially and why?

Accepted Answer

3-substitution is preferred,since this l

Question 17

This substituent deactivates the benzene ring towards electrophilic substitution but directs the incoming group chiefly to the ortho and para positions.

Accepted Answer

A)  -OCH2CH3 
B)  -NO2 
C)  -F 
D)  -CF3 
E)  -NHCOCH3 
A)  -OCH2CH3 
B)  -NO2 
C)  -F 
D)  -CF3 
E)  -NHCOCH3

Question 18

Consider the structures given below.Which of them would be a relatively stable contributor to the hybrid formed when toluene undergoes para 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

Which alkyl halide can undergo both SN1 and SN2 reactions in nonacidic solvents?

Accepted Answer

A)  CH3Br 
B)  CH3CH2CH2Br 
C) 
  
D)  C6H5CH2CH2CH2Br 
E) 
  
A)  CH3Br 
B)  CH3CH2CH2Br 
C) 
  
D)  C6H5CH2CH2CH2Br 
E)

Question 20

How might the following synthesis be carried out:

Accepted Answer

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

Exam 15: Reactions of Aromatic Compounds

Which of the following reactions would yield isopropylbenzene as the major product?

Which is the best sequence of reactions for the following transformation?

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

Which reagent(s)would you use to carry out the following transformation? ethylbenzene-- →\rightarrow→ benzoic acid

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 pyrrole.

When the following substance is treated with Br2/FeBr3,the major product is obtained in good yield,and only very small amounts of minor products are found.What is this major product and why are the minor products not formed to any significant degree? Explain clearly.

Which of the following compounds would be least reactive toward electrophilic substitution?

Undesired polysubstitution of an aromatic nucleus is most likely to be encountered in the case of:

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

How might the following synthesis be carried out:

Based on your knowledge of electrophilic aromatic substitution,predict the preferential position of attack of an electrophile on thiophene,i.e. ,does the electrophile E+ attack carbon 2,or 3? Explain your answer. Which substitution product forms preferentially and why?

What product would result from the following series of reactions,

Which of the following reactions could be used to synthesize tert-butylbenzene?

Which of the following structures would not be a contributor to the resonance hybrid of the benzyl cation?

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

This substituent deactivates the benzene ring towards electrophilic substitution but directs the incoming group chiefly to the ortho and para positions.

Consider the structures given below.Which of them would be a relatively stable contributor to the hybrid formed when toluene undergoes para bromination?

Which alkyl halide can undergo both SN1 and SN2 reactions in nonacidic solvents?

How might the following synthesis be carried out:

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-- $\rightarrow$ benzoic acid

When the following substance is treated with Br₂/FeBr₃,the major product is obtained in good yield,and only very small amounts of minor products are found.What is this major product and why are the minor products not formed to any significant degree? Explain clearly.

Based on your knowledge of electrophilic aromatic substitution,predict the preferential position of attack of an electrophile on thiophene,i.e. ,does the electrophile E⁺ attack carbon 2,or 3? Explain your answer. Which substitution product forms preferentially and why?

Which alkyl halide can undergo both S_N1 and S_N2 reactions in nonacidic solvents?