Question 1

When two different groups are present on a benzene ring,the ____________ generally determines the outcome of an EAS reaction.

Accepted Answer

more power

Question 2

Using a potential energy diagram,explain/illustrate the preferential formation of the 3 substituted product instead of the 2 or 4 product in the electrophilic aromatic substitution of pyridine.

Accepted Answer

The 3 substitution product is

Question 3

When toluene reacts with Cl2,the identity of the major product(s)obtained depends on whether the reaction is carried out in the presence of catalytic amounts of FeCl3,or without catalyst,at high temp.Explain clearly.

Accepted Answer

Reaction with Cl₂/FeCl₃ results in electro

Question 4

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

Accepted Answer

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

Question 5

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

Question 6

Which of the following compounds would be most 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 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

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

The reaction of benzene with   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 10

The rate of solvolysis in ethanol is least for which of these compounds?

Accepted Answer

A)  C6H5CH2Cl 
B) 
  
C)  (C6H5)2CHCl 
D) 
  
E)  (C6H5)3CCl 
A)  C6H5CH2Cl 
B) 
  
C)  (C6H5)2CHCl 
D) 
  
E)  (C6H5)3CCl

Question 11

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 12

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 indole (shown).

Accepted Answer

3-substitution is preferred,since this l

Question 13

With the exception of halogens,activating groups are ____________ directors and deactivating groups are _________ directors.

Accepted Answer

The answer of With the exception of halogens,activating groups are...

Question 14

Which reagent or test could you use to distinguish between phenylacetylene and vinylbenzene?

Accepted Answer

A)  NaOH/H2O 
B)  Br2/CCl4 
C)  IR Spectroscopy 
D)  CrO3/H2SO4 
E)  Concd.H2SO4 
A)  NaOH/H2O 
B)  Br2/CCl4 
C)  IR Spectroscopy 
D)  CrO3/H2SO4 
E)  Concd.H2SO4

Question 15

Which of the following compounds would be most 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 16

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

Accepted Answer

The 2 substitution product is favored si

Question 17

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

Question 18

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 19

Toluene is subjected to the action of the following reagents in the order given: (1)KMnO4,OH-,heat;then H3O+ (2)HNO3,H2SO4 (3)Br2,FeBr3 What is the final product of this sequence?

Accepted Answer

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

Question 20

Toluene is subjected to the action of the following reagents in the order given: (1)KMnO4,OH-,heat;then H3O+ (2)HNO3,H2SO4 (3)Cl2,FeCl3 What is the final product of this sequence?

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

When two different groups are present on a benzene ring,the ____________ generally determines the outcome of an EAS reaction.

Using a potential energy diagram,explain/illustrate the preferential formation of the 3 substituted product instead of the 2 or 4 product in the electrophilic aromatic substitution of pyridine.

When toluene reacts with Cl2,the identity of the major product(s)obtained depends on whether the reaction is carried out in the presence of catalytic amounts of FeCl3,or without catalyst,at high temp.Explain clearly.

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

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

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

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?

The reaction of benzene with in the presence of anhydrous aluminum chloride produces principally which of these?

The rate of solvolysis in ethanol is least for which of these compounds?

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

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 indole (shown).

With the exception of halogens,activating groups are ____________ directors and deactivating groups are _________ directors.

Which reagent or test could you use to distinguish between phenylacetylene and vinylbenzene?

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

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

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

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.

Toluene is subjected to the action of the following reagents in the order given: (1)KMnO4,OH-,heat;then H3O+ (2)HNO3,H2SO4 (3)Br2,FeBr3 What is the final product of this sequence?

Toluene is subjected to the action of the following reagents in the order given: (1)KMnO4,OH-,heat;then H3O+ (2)HNO3,H2SO4 (3)Cl2,FeCl3 What is the final product of this sequence?

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

When toluene reacts with Cl₂,the identity of the major product(s)obtained depends on whether the reaction is carried out in the presence of catalytic amounts of FeCl₃,or without catalyst,at high temp.Explain clearly.

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

With the exception of halogens,activating groups are ____ directors and deactivating groups are _ directors.

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

Toluene is subjected to the action of the following reagents in the order given: (1)KMnO₄,OH^-,heat;then H₃O⁺ (2)HNO₃,H₂SO₄ (3)Br₂,FeBr₃ What is the final product of this sequence?

Toluene is subjected to the action of the following reagents in the order given: (1)KMnO₄,OH^-,heat;then H₃O⁺ (2)HNO₃,H₂SO₄ (3)Cl₂,FeCl₃ What is the final product of this sequence?