Question 1

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 2

Based on your knowledge of electrophilic aromatic substitution,predict the preferential position of nitration of naphthalene,i.e. ,does the NO2+ attack carbon 1,or 2? Explain your answer.   Which substitution product forms preferentially and why?

Accepted Answer

The 1 substitution product is favored si

Question 3

Using a potential energy diagram,explain/illustrate the preferential formation of the 3 substituted product instead of the 2 product in the electrophilic aromatic substitution of benzo[b] furane (shown).

Accepted Answer

3-substitution is preferred,since this l

Question 4

What would be the major product of 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 5

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 6

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 + SOCl2 --$\rightarrow$ 
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 + SOCl2 --$\rightarrow$ 
D)  C6H5CH=CH2 + HCl,peroxide --$\rightarrow$ 
E)  C6H6 + CH3CH2Cl,AlCl3 --$\rightarrow$

Question 7

This molecule does not normally participate as a reactant in a Friedel-Crafts reaction.

Accepted Answer

A)  Benzene 
B)  Chlorobenzene 
C)  Nitrobenzene 
D)  Toluene 
E)  tert-Butylbenzene 
A)  Benzene 
B)  Chlorobenzene 
C)  Nitrobenzene 
D)  Toluene 
E)  tert-Butylbenzene

Question 8

Which alkyl halide would be most reactive in an SN1 reaction?

Accepted Answer

A)  C6H5CH2CH2CH2Br 
B) 
  
C) 
  
D) 
  
E) 
  
A)  C6H5CH2CH2CH2Br 
B) 
  
C) 
  
D) 
  
E)

Question 9

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

Accepted Answer

A)  i)HNO3,H2SO4;ii)CH3MgBr,Et2O;iii)H2O,NH4Cl 
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)H2O,NH4Cl 
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 10

Which of the following structures contribute(s)to the resonance hybrid of the intermediate formed when acetanilide undergoes para-bromination?

Accepted Answer

A)  I 
B)  II 
C)  III 
D)  IV 
E)  All of the above 
A)  I 
B)  II 
C)  III 
D)  IV 
E)  All of the above

Question 11

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

Accepted Answer

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

Question 12

(Trifluoromethyl)benzene,C6H5CF3,will

Accepted Answer

A)  nitrate rapidly in the ortho-para positions. 
B)  nitrate slowly in the ortho-para positions. 
C)  nitrate rapidly in the meta position. 
D)  nitrate slowly in the meta position. 
E)  fail to nitrate under any conditions. 
A)  nitrate rapidly in the ortho-para positions. 
B)  nitrate slowly in the ortho-para positions. 
C)  nitrate rapidly in the meta position. 
D)  nitrate slowly in the meta position. 
E)  fail to nitrate under any conditions.

Question 13

Based on your knowledge of electrophilic aromatic substitution,predict the position of attack of an electrophile on pyridine,i.e. ,does the electrophile E+ attack carbon 2,3,or 4? Explain your answer.   Which substitution product(s)forms and why?

Accepted Answer

The 3 substitution product is

Question 14

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 15

Which of the following structures does not contribute to the resonance hybrid of the intermediate formed when nitrobenzene undergoes meta-chlorination?

Accepted Answer

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

Question 16

What reagent can effect the following transformation?

Accepted Answer

A)  CO2;then H3O+ 
B)  H3O+,heat 
C)  Mg;then CO2;then H3O+ 
D)  H2O2,heat 
E)  KMnO4,OH-,heat;then H3O+ 
A)  CO2;then H3O+ 
B)  H3O+,heat 
C)  Mg;then CO2;then H3O+ 
D)  H2O2,heat 
E)  KMnO4,OH-,heat;then H3O+

Question 17

Which of the following structures contribute(s)to the resonance hybrid of the intermediate formed when bromobenzene undergoes para-chlorination?

Accepted Answer

A)  I 
B)  II 
C)  III 
D)  IV 
E)  All of the above 
A)  I 
B)  II 
C)  III 
D)  IV 
E)  All of the above

Question 18

Although benzene is susceptible to electrophilic attack,its special stability causes it to undergo ______________ rather than ____________ reactions.

Accepted Answer

substituti

Question 19

What would be the major product of 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

What would be the major product of 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

Exam 15: Reactions of Aromatic Compounds

What product would result from the following series of reactions,

Based on your knowledge of electrophilic aromatic substitution,predict the preferential position of nitration of naphthalene,i.e. ,does the NO2+ attack carbon 1,or 2? Explain your answer. Which substitution product forms preferentially and why?

Using a potential energy diagram,explain/illustrate the preferential formation of the 3 substituted product instead of the 2 product in the electrophilic aromatic substitution of benzo[b] furane (shown).

What would be the major product of the following reaction?

What would be the product of the following reaction sequence?

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

This molecule does not normally participate as a reactant in a Friedel-Crafts reaction.

Which alkyl halide would be most reactive in an SN1 reaction?

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

Which of the following structures contribute(s)to the resonance hybrid of the intermediate formed when acetanilide undergoes para-bromination?

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

(Trifluoromethyl)benzene,C6H5CF3,will

Based on your knowledge of electrophilic aromatic substitution,predict the position of attack of an electrophile on pyridine,i.e. ,does the electrophile E+ attack carbon 2,3,or 4? Explain your answer. Which substitution product(s)forms and why?

What product would result from the following series of reactions,

Which of the following structures does not contribute to the resonance hybrid of the intermediate formed when nitrobenzene undergoes meta-chlorination?

What reagent can effect the following transformation?

Which of the following structures contribute(s)to the resonance hybrid of the intermediate formed when bromobenzene undergoes para-chlorination?

Although benzene is susceptible to electrophilic attack,its special stability causes it to undergo ______________ rather than ____________ reactions.

What would be the major product of the following reaction?

What would be the major product 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

Based on your knowledge of electrophilic aromatic substitution,predict the preferential position of nitration of naphthalene,i.e. ,does the NO₂⁺ attack carbon 1,or 2? Explain your answer. Which substitution product forms preferentially and why?

Which alkyl halide would be most reactive in an S_N1 reaction?

(Trifluoromethyl)benzene,C₆H₅CF₃,will

Based on your knowledge of electrophilic aromatic substitution,predict the position of attack of an electrophile on pyridine,i.e. ,does the electrophile E⁺ attack carbon 2,3,or 4? Explain your answer. Which substitution product(s)forms and why?

Although benzene is susceptible to electrophilic attack,its special stability causes it to undergo __ rather than reactions.