Question 1

Arrange the following compounds in order of decreasing reactivity in electrophilic substitution:

Accepted Answer

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

Question 2

Benzene is susceptible to electrophilic attack primarily because of its _____________.

Accepted Answer

The answer of Benzene is susceptible to electrophilic attack primarily...

Question 3

What 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 4

Draw a mechanism that explains the formation of the following product in this Friedel-Crafts alkylation:

Accepted Answer

The answer of Draw a mechanism that explains the formation...

Question 5

Based on your knowledge of electrophilic aromatic substitution,and assuming the pyrrole ring of indole (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 6

Acid-catalyzed hydration of 1-phenyl-1-pentene gives 1-phenyl-1-pentanol almost exclusively;the other possible hydration product,1-phenyl-2-pentanol,is not detected at all.Explain clearly.

Accepted Answer

Acid catalyzed hydration of an alkene oc

Question 7

Which of the following is not a meta-directing substituent when present on the benzene ring?

Accepted Answer

A)  -NHCOCH3 
B)  -NO2 
C)  -N(CH3)3+ 
D)  -C$ \equiv$N 
E)  -CO2H 
A)  -NHCOCH3 
B)  -NO2 
C)  -N(CH3)3+ 
D)  -C$ \equiv$N 
E)  -CO2H

Question 8

What is the chief product of the Friedel-Crafts alkylation of benzene with 1-butene and HF?

Accepted Answer

A)  butylbenzene 
B)  2-phenylbutane 
C)  2-methyl-1-phenylpropane 
D)  t-butylbenzene 
E)  2,2-diphenylbutane 
A)  butylbenzene 
B)  2-phenylbutane 
C)  2-methyl-1-phenylpropane 
D)  t-butylbenzene 
E)  2,2-diphenylbutane

Question 9

What is the chief product of the Friedel-Crafts alkylation of benzene with 1-butene and AlCl3?

Accepted Answer

A)  butylbenzene 
B)  2-phenylbutane 
C)  2-methyl-1-phenylpropane 
D)  t-butylbenzene 
E)  2,2-diphenylbutane 
A)  butylbenzene 
B)  2-phenylbutane 
C)  2-methyl-1-phenylpropane 
D)  t-butylbenzene 
E)  2,2-diphenylbutane

Question 10

The major product(s)of the following reaction,

Accepted Answer

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

Question 11

What would be the major product(s)of the following reaction?

Accepted Answer

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

Question 12

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

Accepted Answer

A)  Cl2,light,and heat 
B)  Cl2,FeCl3 
C)  SOCl2 
D)  C2H5Cl,AlCl3 
E)  HCl,peroxides 
A)  Cl2,light,and heat 
B)  Cl2,FeCl3 
C)  SOCl2 
D)  C2H5Cl,AlCl3 
E)  HCl,peroxides

Question 13

Which of the following reactions would produce isopropylbenzene?

Accepted Answer

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

Question 14

Based on your knowledge of electrophilic aromatic substitution,predict the preferential
position of attack of an electrophile on furan,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 15

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

Accepted Answer

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

Question 16

Which of the following reactions would give the product(s)indicated in substantial amounts (i.e. ,in greater than 50% yield)?

Accepted Answer

A)  I 
B)  II 
C)  III 
D)  All of these 
E)  None of these 
A)  I 
B)  II 
C)  III 
D)  All of these 
E)  None of these

Question 17

Which of the following compounds would be most reactive toward 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 18

Suggest a reasonable synthetic strategy for the synthesis of 3,5-dinitrobenzyl alcohol from benzaldehyde.

Accepted Answer

The answer of Suggest a reasonable synthetic strategy for the...

Question 19

What would be the major product(s)of the following reaction?

Accepted Answer

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

Question 20

Which would be the major product(s)of the following reaction?

Accepted Answer

A)  I 
B)  II 
C)  III 
D)  I and II in roughly equal amounts 
E)  I and III in roughly equal amounts 
A)  I 
B)  II 
C)  III 
D)  I and II in roughly equal amounts 
E)  I and III in roughly equal amounts

Exam 15: Reactions of Aromatic Compounds

Arrange the following compounds in order of decreasing reactivity in electrophilic substitution:

Benzene is susceptible to electrophilic attack primarily because of its _____________.

What would be the product of the following reaction sequence?

Draw a mechanism that explains the formation of the following product in this Friedel-Crafts alkylation:

Acid-catalyzed hydration of 1-phenyl-1-pentene gives 1-phenyl-1-pentanol almost exclusively;the other possible hydration product,1-phenyl-2-pentanol,is not detected at all.Explain clearly.

Which of the following is not a meta-directing substituent when present on the benzene ring?

What is the chief product of the Friedel-Crafts alkylation of benzene with 1-butene and HF?

What is the chief product of the Friedel-Crafts alkylation of benzene with 1-butene and AlCl3?

The major product(s)of the following reaction,

What would be the major product(s)of the following reaction?

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

Which of the following reactions would produce isopropylbenzene?

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

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

Which of the following reactions would give the product(s)indicated in substantial amounts (i.e. ,in greater than 50% yield)?

Which of the following compounds would be most reactive toward ring bromination?

Suggest a reasonable synthetic strategy for the synthesis of 3,5-dinitrobenzyl alcohol from benzaldehyde.

What would be the major product(s)of the following reaction?

Which would be the major product(s)of the following reaction?

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

What is the chief product of the Friedel-Crafts alkylation of benzene with 1-butene and AlCl₃?

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

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