Question 1

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 2

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 3

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 4

Which of the following reactions would yield isopropylbenzene as the major product?

Accepted Answer

A)    
B)    
C)    
D)    
E) All of these choices. 
A)    
B)    
C)    
D)    
E) All of these choices.

Question 5

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 6

Which reagent(s)would you use to carry out the following transformation? isopropylbenzene $\to$ 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 7

What product would result from the following series of reactions,

Accepted Answer

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

Question 8

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 9

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 10

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 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

The major product,D,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 13

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 14

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 15

What reagent can effect the following transformation?

Accepted Answer

A) CO2; then H3O+ 
B) H3O+,heat 
C) Mg; then CO2; then H3O+ 
D) H2O2,heat 
E) KMnO4,OH-,heat; then H3O+ 
A) CO2; then H3O+ 
B) H3O+,heat 
C) Mg; then CO2; then H3O+ 
D) H2O2,heat 
E) KMnO4,OH-,heat; then H3O+

Question 16

Suggest a reasonable synthetic strategy for the synthesis of 4-methyl-1-phenyl-1-pentanol from 4-methylpentanoyl chloride,(CH3)2CHCH2CH2COCl

Accepted Answer

Question 17

When toluene is reacted in turn with 1)Cl2 (large excess),heat,and light and 2)Br2,FeBr3,the chief product is:

Accepted Answer

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

Question 18

Which reagent(s)would you use to carry out the following transformation? t-butylbenzene $\to$ 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 19

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 20

Based on your knowledge of electrophilic aromatic substitution,predict the position of attack of an electrophile on pyridine,i.e.,does the electrophile E+ attack carbon 2,3,or 4? Explain your answer.   Which substitution product(s)forms and why?

Accepted Answer

The 3 substitution product is

Exam 15: Reactions of Aromatic Compounds

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

What would be the major product of the following reaction?

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).

Which of the following reactions would yield isopropylbenzene as the major product?

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

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

What product would result from the following series of reactions,

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

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

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

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

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

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

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?

What reagent can effect the following transformation?

Suggest a reasonable synthetic strategy for the synthesis of 4-methyl-1-phenyl-1-pentanol from 4-methylpentanoyl chloride,(CH3)2CHCH2CH2COCl

When toluene is reacted in turn with 1)Cl2 (large excess),heat,and light and 2)Br2,FeBr3,the chief product is:

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

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

Based on your knowledge of electrophilic aromatic substitution,predict the position of attack of an electrophile on pyridine,i.e.,does the electrophile E+ attack carbon 2,3,or 4? Explain your answer. Which substitution product(s)forms and why?

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

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

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

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

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?

Suggest a reasonable synthetic strategy for the synthesis of 4-methyl-1-phenyl-1-pentanol from 4-methylpentanoyl chloride,(CH₃)₂CHCH₂CH₂COCl

When toluene is reacted in turn with 1)Cl₂ (large excess),heat,and light and 2)Br₂,FeBr₃,the chief product is:

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

Based on your knowledge of electrophilic aromatic substitution,predict the position of attack of an electrophile on pyridine,i.e.,does the electrophile E⁺ attack carbon 2,3,or 4? Explain your answer. Which substitution product(s)forms and why?