Question 1

Which compound is capable of undergoing both SN1 and SN2 reactions in ordinary nonacidic solvents?

Accepted Answer

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

Question 2

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 A

Question 3

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 C

Question 4

Which reagent(s)would you use to carry out the following transformation? t-butylbenzene --$\rightarrow$p-chloro substitution product

Accepted Answer

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

Question 5

Which reagent would you use as the basis for a simple chemical test that would distinguish between toluene and vinylbenzene (C6H5CH=CH2)?

Accepted Answer

A)  NaOH/H2O 
B)  Br2/CCl4 
C)  NaBH4 
D)  HCl/H2O 
E)  NaI in acetone 
A)  NaOH/H2O 
B)  Br2/CCl4 
C)  NaBH4 
D)  HCl/H2O 
E)  NaI in acetone

Question 6

A good synthesis of   would be:

Accepted Answer

A) 
  
B) 
  
C) 
  
D)  More than one of these 
E)  None of these 
A) 
  
B) 
  
C) 
  
D)  More than one of these 
E)  None of these

Question 7

Which of the following compounds would you expect to be most reactive toward ring nitration?

Accepted Answer

A)  Benzene 
B)  Toluene 
C)  m-Xylene 
D)  p-Xylene 
E)  Benzoic acid 
A)  Benzene 
B)  Toluene 
C)  m-Xylene 
D)  p-Xylene 
E)  Benzoic acid

Question 8

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 9

Which of the following compounds would be most reactive toward 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 10

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

Accepted Answer

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

Question 11

Benzoic acid can be prepared by the oxidation of which of the following compounds:

Accepted Answer

A)  C6H5CH=CH2 
B)  C6H5C$ \equiv$CH 
C)  C6H5COCH3 
D)  C6H5CH2CH2CH3 
E)  All of these 
A)  C6H5CH=CH2 
B)  C6H5C$ \equiv$CH 
C)  C6H5COCH3 
D)  C6H5CH2CH2CH3 
E)  All of these

Question 12

Which of the following compounds would yield 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 13

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 14

Which of these compounds gives essentially a single product on electrophilic substitution of a third group?

Accepted Answer

A)  p-chlorotoluene 
B)  m-ethylanisole 
C)  1-bromo-2-chlorobenzene 
D)  m-xylene 
E)  3-hydroxybenzoic acid 
A)  p-chlorotoluene 
B)  m-ethylanisole 
C)  1-bromo-2-chlorobenzene 
D)  m-xylene 
E)  3-hydroxybenzoic acid

Question 15

Which one of these molecules can be a reactant in a Friedel-Crafts reaction?

Accepted Answer

A)  Aniline 
B)  Nitrobenzene 
C)  Chloroethene 
D)  Bromobenzene 
E)  p-Bromonitrobenzene 
A)  Aniline 
B)  Nitrobenzene 
C)  Chloroethene 
D)  Bromobenzene 
E)  p-Bromonitrobenzene

Question 16

The reaction of benzene with (CH3)3CCH2Cl in the presence of anhydrous aluminum chloride produces principally which of these?

Accepted Answer

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

Question 17

The electrophilic bromination or chlorination of benzene requires,in addition to the halogen:

Accepted Answer

A)  a hydroxide ion. 
B)  a Lewis base. 
C)  a Lewis acid. 
D)  peroxide. 
E)  ultraviolet light. 
A)  a hydroxide ion. 
B)  a Lewis base. 
C)  a Lewis acid. 
D)  peroxide. 
E)  ultraviolet light.

Question 18

Which of the following structures contribute(s)to the resonance hybrid of the intermediate formed when chlorobenzene 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 19

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

Accepted Answer

A)  i)HNO3,H2SO4;ii)2EtMgBr,Et2O;iii)NH4Cl 
B)  i)2EtMgBr,Et2O;ii)H3O+;iii)HNO3,H2SO4 
C)  i)HNO3,H2SO4;ii)NaBH4,H2O;iii)2EtMgBr,Et2O 
D)  i)LAH;ii)2EtLi,Et2O;iii)HNO3,H2SO4,heat 
E)  None of these syntheses is satisfactory. 
A)  i)HNO3,H2SO4;ii)2EtMgBr,Et2O;iii)NH4Cl 
B)  i)2EtMgBr,Et2O;ii)H3O+;iii)HNO3,H2SO4 
C)  i)HNO3,H2SO4;ii)NaBH4,H2O;iii)2EtMgBr,Et2O 
D)  i)LAH;ii)2EtLi,Et2O;iii)HNO3,H2SO4,heat 
E)  None of these syntheses is satisfactory.

Question 20

What might be predicted to happen when the following substance undergoes Friedel-Crafts acylation?

Accepted Answer

A)  Substitution occurs in ring B,p- to the methylene group. 
B)  Substitution occurs in ring A,o- to the nitro group. 
C)  Substitution occurs in ring A,o- to the methylene group. 
D)  Substitution occurs in ring B,m- to the methylene group. 
E)  None of the above.No reaction will occur. 
A)  Substitution occurs in ring B,p- to the methylene group. 
B)  Substitution occurs in ring A,o- to the nitro group. 
C)  Substitution occurs in ring A,o- to the methylene group. 
D)  Substitution occurs in ring B,m- to the methylene group. 
E)  None of the above.No reaction will occur.

Exam 15: Reactions of Aromatic Compounds

Which compound is capable of undergoing both SN1 and SN2 reactions in ordinary nonacidic solvents?

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

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

Which reagent(s)would you use to carry out the following transformation? t-butylbenzene -- →\rightarrow→ p-chloro substitution product

Which reagent would you use as the basis for a simple chemical test that would distinguish between toluene and vinylbenzene (C6H5CH=CH2)?

A good synthesis of would be:

Which of the following compounds would you expect to be most reactive toward ring nitration?

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

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

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

Benzoic acid can be prepared by the oxidation of which of the following compounds:

Which of the following compounds would yield the greatest amount of meta product when subjected to ring nitration?

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

Which of these compounds gives essentially a single product on electrophilic substitution of a third group?

Which one of these molecules can be a reactant in a Friedel-Crafts reaction?

The reaction of benzene with (CH3)3CCH2Cl in the presence of anhydrous aluminum chloride produces principally which of these?

The electrophilic bromination or chlorination of benzene requires,in addition to the halogen:

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

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

What might be predicted to happen when the following substance undergoes Friedel-Crafts acylation?

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 compound is capable of undergoing both S_N1 and S_N2 reactions in ordinary nonacidic solvents?

Which reagent(s)would you use to carry out the following transformation? t-butylbenzene -- $\rightarrow$ p-chloro substitution product

Which reagent would you use as the basis for a simple chemical test that would distinguish between toluene and vinylbenzene (C₆H₅CH=CH₂)?

The reaction of benzene with (CH₃)₃CCH₂Cl in the presence of anhydrous aluminum chloride produces principally which of these?