Question 1

Which of these species is/are proposed as intermediate(s)in the mechanism for the Birch reduction?

Accepted Answer

A) Radical 
B) Carbanion 
C) Radical anion 
D) Two of these choices. 
E) All of these choices. 
A) Radical 
B) Carbanion 
C) Radical anion 
D) Two of these choices. 
E) All of these choices.

Question 2

What product would result from the following series of reactions:

Accepted Answer

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

Question 3

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 furan.

Accepted Answer

The 2 substitution product is favored si

Question 4

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

Question 5

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 6

Which of these is the rate-determining step in the sulfonation of benzene?

Accepted Answer

A) Formation of SO3 from sulfuric acid 
B) Protonation of SO3 sulfuric acid 
C) Addition of SO3H+ to benzene to form the arenium ion 
D) Loss of a proton from the arenium ion to form benzenesulfonic acid 
E) None of these choices. 
A) Formation of SO3 from sulfuric acid 
B) Protonation of SO3 sulfuric acid 
C) Addition of SO3H+ to benzene to form the arenium ion 
D) Loss of a proton from the arenium ion to form benzenesulfonic acid 
E) None of these choices.

Question 7

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 8

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 9

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 thiophene.

Accepted Answer

The 2 substitution product is favored si

Question 10

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 11

Which of the following would be the best synthesis of 1,4-dimethyl-2-nitrobenzene?

Accepted Answer

A)    
B)    
C)    
D)    
E) All of these choices are equally good. 
A)    
B)    
C)    
D)    
E) All of these choices are equally good.

Question 12

Suggest a reasonable synthetic strategy for the synthesis of 6-methyl-3-phenyl-3-heptanol from 4-methylpentanoyl chloride,(CH3)2CHCH2CH2COCl

Accepted Answer

Question 13

The major product(s),A,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 14

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

Question 15

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

Accepted Answer

A)    
B)    
C)    
D) All of these choices. 
E) None of these choices. 
A)    
B)    
C)    
D) All of these choices. 
E) None of these choices.

Question 16

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 17

Which would be the product,X,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 18

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 19

Which reagent(s)would you use to carry out the following transformation? ethylbenzene $\to$  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 20

Which reagent(s)would you use to carry out the following transformation? ethylbenzene $\to$ 1-chloro-1-phenylethane

Accepted Answer

A) Cl2,light,or heat 
B) Cl2,FeCl3 
C) SOCl2 
D) C2H5Cl,AlCl3 
E) HCl,O2 
A) Cl2,light,or heat 
B) Cl2,FeCl3 
C) SOCl2 
D) C2H5Cl,AlCl3 
E) HCl,O2

Exam 15: Reactions of Aromatic Compounds

Which of these species is/are proposed as intermediate(s)in the mechanism for the Birch reduction?

What product would result from the following series of reactions:

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 furan.

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

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

Which of these is the rate-determining step in the sulfonation of benzene?

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

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

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 thiophene.

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

Which of the following would be the best synthesis of 1,4-dimethyl-2-nitrobenzene?

Suggest a reasonable synthetic strategy for the synthesis of 6-methyl-3-phenyl-3-heptanol from 4-methylpentanoyl chloride,(CH3)2CHCH2CH2COCl

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

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

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

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

Which would be the product,X,of the following reaction sequence?

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? ethylbenzene →\to→ benzoic acid

Which reagent(s)would you use to carry out the following transformation? ethylbenzene →\to→ 1-chloro-1-phenylethane

The Basics

Families of Carbon

Acids and Bases

Nomenclature and Conformations of Alkanes and Cycloalkanes

Stereochemistry

Nucleophilic Reactions

Alkenes and Alkynes I

Alkenes and Alkynes II

Nuclear Magnetic Resonance and Mass Spectrometry

Radical Reactions

Alcohols and Ethers

Alcohols From Carbonyl Compounds

Conjugated Unsaturated Systems

Aromatic Compounds

Aldehydes and Ketones

Carboxylic Acids and Their Derivatives

Reactions at the Α Carbon of Carbonyl Compounds

Condensation and Conjugate Addition Reactions of Carbonyl Compounds

Amines

Transition Metal Complexes

Carbohydrates

Lipids

Amino Acids and Proteins

Nucleic Acids and Protein Synthesis

Filters

Suggest a reasonable synthetic strategy for the synthesis of 6-methyl-3-phenyl-3-heptanol from 4-methylpentanoyl chloride,(CH₃)₂CHCH₂CH₂COCl

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

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

Which reagent(s)would you use to carry out the following transformation? ethylbenzene $\to$ 1-chloro-1-phenylethane