Question 1

Which reagent(s)would you use to synthesize 2- and 4-bromo-1-cyclopentylbenzene from cyclopentylbenzene?

Accepted Answer

A)  N-Bromosuccinimide (NBS),CCl4,light 
B)  PBr3 
C)  Br2,FeBr3 
D)  CH3CH2Br,AlBr3 
E)  HBr,ROOR 
A)  N-Bromosuccinimide (NBS),CCl4,light 
B)  PBr3 
C)  Br2,FeBr3 
D)  CH3CH2Br,AlBr3 
E)  HBr,ROOR

Question 2

Substituent groups affect both _____________ and _______________ in electrophilic aromatic substitution reactions.

Accepted Answer

reactivity

Question 3

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 4

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

Question 5

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

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 6

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 7

Propose a reasonable synthesis of the following compound from benzene.

Accepted Answer

The answer of Propose a reasonable synthesis of the following...

Question 8

Which reagent(s)would you use to carry out the following transformation? isopropylbenzene --$\rightarrow$ 2- and 4-chloro-1-isopropylbenzene

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 9

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

Accepted Answer

A)  i)SOCl2;ii)C6H6,AlCl3;iii)Zn(Hg),HCl;iv)HNO3,H2SO4 
B)  i)SOCl2;ii)HNO3,H2SO4;iii)C6H6,AlCl3;iv)H2,Ni 
C)  i)HNO3,H2SO4;ii)SOCl2;iii)C6H6,AlCl3;iv)Zn(Hg),HCl 
D)  i)PBr3;ii)HNO3,H2SO4;iii)C6H6,AlCl3;iv)NaBH4,H2O 
E)  Two of these syntheses are satisfactory. 
A)  i)SOCl2;ii)C6H6,AlCl3;iii)Zn(Hg),HCl;iv)HNO3,H2SO4 
B)  i)SOCl2;ii)HNO3,H2SO4;iii)C6H6,AlCl3;iv)H2,Ni 
C)  i)HNO3,H2SO4;ii)SOCl2;iii)C6H6,AlCl3;iv)Zn(Hg),HCl 
D)  i)PBr3;ii)HNO3,H2SO4;iii)C6H6,AlCl3;iv)NaBH4,H2O 
E)  Two of these syntheses are satisfactory.

Question 10

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 11

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 12

Which reagent would you use to carry out the following transformation? tert-butylbenzene
--$\rightarrow$
P-tert-butylbenzenesulfonic acid
+
O-tert-butylbenzenesulfonic acid

Accepted Answer

A)  HNO3/H2SO4 
B)  tert-C4H9Cl/AlCl3 
C)  H2SO3/peroxides 
D)  SO3/H2SO4 
E)  SO2/H2SO3 
A)  HNO3/H2SO4 
B)  tert-C4H9Cl/AlCl3 
C)  H2SO3/peroxides 
D)  SO3/H2SO4 
E)  SO2/H2SO3

Question 13

Which would be a good synthesis of m-nitrobenzoic acid?

Accepted Answer

A) 
  
B) 
  
C) 
  
D)  More than one of the above 
E)  None of the above 
A) 
  
B) 
  
C) 
  
D)  More than one of the above 
E)  None of the above

Question 14

Which 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 15

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

Accepted Answer

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

Question 16

Which alkyl halide would be most reactive in an SN2 reaction?

Accepted Answer

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

Question 17

Which of the following compounds would be most reactive to 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

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 19

Which of the following carbocations would be most stable?

Accepted Answer

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

Question 20

What would you expect to be the major product(s)obtained from the mononitration of m-dichlorobenzene?

Accepted Answer

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

Exam 15: Reactions of Aromatic Compounds

Which reagent(s)would you use to synthesize 2- and 4-bromo-1-cyclopentylbenzene from cyclopentylbenzene?

Substituent groups affect both _____________ and _______________ in electrophilic aromatic substitution reactions.

The major product(s)of the following reaction,

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

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

What would be the major product of the following reaction?

Propose a reasonable synthesis of the following compound from benzene.

Which reagent(s)would you use to carry out the following transformation? isopropylbenzene -- →\rightarrow→ 2- and 4-chloro-1-isopropylbenzene

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

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

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

Which reagent would you use to carry out the following transformation? tert-butylbenzene -- →\rightarrow→ P-tert-butylbenzenesulfonic acid + O-tert-butylbenzenesulfonic acid

Which would be a good synthesis of m-nitrobenzoic acid?

Which would be the product of the following reaction sequence?

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

Which alkyl halide would be most reactive in an SN2 reaction?

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

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

Which of the following carbocations would be most stable?

What would you expect to be the major product(s)obtained from the mononitration of m-dichlorobenzene?

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

Substituent groups affect both _ and ___ in electrophilic aromatic substitution reactions.

Which reagent(s)would you use to carry out the following transformation? isopropylbenzene -- $\rightarrow$ 2- and 4-chloro-1-isopropylbenzene

Which reagent would you use to carry out the following transformation? tert-butylbenzene -- $\rightarrow$ P-tert-butylbenzenesulfonic acid + O-tert-butylbenzenesulfonic acid

Which alkyl halide would be most reactive in an S_N2 reaction?