Question 1

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 2

Based on your knowledge of electrophilic aromatic substitution,and assuming the thiophene ring of benzo[b]thiophene (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 3

Which reagent(s)would you use to carry out the following transformation? toluene --$\rightarrow$benzyl bromide

Accepted Answer

A)  Br2,FeBr3 
B)  N-Bromosuccinimide,ROOR,h$\nu$ 
C)  HBr 
D)  Br2/CCl4 
E)  NaBr,H2SO4 
A)  Br2,FeBr3 
B)  N-Bromosuccinimide,ROOR,h$\nu$ 
C)  HBr 
D)  Br2/CCl4 
E)  NaBr,H2SO4

Question 4

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 5

Electron-withdrawing groups decrease the electron density on the aromatic ring,causing it to be less reactive than benzene itself towards EAS.These types of groups are called _____________ groups.

Accepted Answer

The answer of Electron-withdrawing groups decrease the electron density on...

Question 6

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

Accepted Answer

Question 7

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 8

Starting with benzene,the best method for preparing m-nitrobenzoic acid is:

Accepted Answer

A)  HNO3/H2SO4;then CH3Cl/AlCl3;then separation of isomers;then KMnO4/
-OH/heat,followed by H3O+. 
B)  CH3Cl/AlCl3;then HNO3/H2SO4;then separation of isomers;then KMnO4/
-OH/heat,followed by H3O+. 
C)  CH3Cl/AlCl3;then KMnO4/-OH/heat,followed by H3O+;then HNO3/H2SO4. 
D)  HNO3/H2SO4;then KMnO4/-OH/heat,followed by H3O+;then CH3Cl/AlCl3. 
E)  HNO3/H2SO4;then CO2,followed by H3O+. 
A)  HNO3/H2SO4;then CH3Cl/AlCl3;then separation of isomers;then KMnO4/
-OH/heat,followed by H3O+. 
B)  CH3Cl/AlCl3;then HNO3/H2SO4;then separation of isomers;then KMnO4/
-OH/heat,followed by H3O+. 
C)  CH3Cl/AlCl3;then KMnO4/-OH/heat,followed by H3O+;then HNO3/H2SO4. 
D)  HNO3/H2SO4;then KMnO4/-OH/heat,followed by H3O+;then CH3Cl/AlCl3. 
E)  HNO3/H2SO4;then CO2,followed by H3O+.

Question 9

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

Accepted Answer

A)  Br2,heat,and light 
B)  Cl2,FeCl3 
C)  KMnO4,OH-,heat (then H3O+) 
D)  HNO3/H2SO4 
E)  SO3/H2SO4 
A)  Br2,heat,and light 
B)  Cl2,FeCl3 
C)  KMnO4,OH-,heat (then H3O+) 
D)  HNO3/H2SO4 
E)  SO3/H2SO4

Question 10

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

Question 11

Which of the following compounds would be least reactive toward electrophilic substitution?

Accepted Answer

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

Question 12

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 13

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

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

Which reagent(s)would you use to carry out the following transformation? toluene -- $\rightarrow$ benzyl bromide

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

Electron-withdrawing groups decrease the electron density on the aromatic ring,causing it to be less reactive than benzene itself towards EAS.These types of groups are called _____________ groups.

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

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

Starting with benzene,the best method for preparing m-nitrobenzoic acid is:

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

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

Which of the following compounds would be least reactive toward electrophilic substitution?

What would you expect to be the major product obtained from 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

Exam 15: Reactions of Aromatic Compounds

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

Which reagent(s)would you use to carry out the following transformation? toluene -- →\rightarrow→ benzyl bromide

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

Electron-withdrawing groups decrease the electron density on the aromatic ring,causing it to be less reactive than benzene itself towards EAS.These types of groups are called _____________ groups.

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

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

Starting with benzene,the best method for preparing m-nitrobenzoic acid is:

Which reagent(s)would you use to carry out the following transformation? toluene -- →\rightarrow→ benzoic acid

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

Which of the following compounds would be least reactive toward electrophilic substitution?

What would you expect to be the major product obtained from 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

Which reagent(s)would you use to carry out the following transformation? toluene -- $\rightarrow$ benzyl bromide

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

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