Deck 18: Reactions of Benzene and Substituted Benzenes

Question 1

Which of the following reactions of benzene does not proceed by electrophilic aromatic substitution?

A) halogenation
B) nitration
C) sulfonation
D) Friedel-Crafts alkylation and acylation
E) All of these are electrophilic aromatic substitution reactions.

Answer 1

All of these are electrophilic aromatic substitution reactions.

Question 2

Which of the following statements is not true about the sulfonation of benzene?

A) Heating sulfuric acid leads to formation of the ⁺SO₃H electrophile.
B) Sulfonation is irreversible.
C) Sulfonation occurs through an electrophilic aromatic substitution mechanism.
D) The rate limiting step is formation of a resonance stabilized carbocation intermediate.
E) All of these statements are true.

Answer 2

Sulfonation is irreversible.

Question 3

Which set of reagents should be used to prepare n-propylbenzene?

A) benzene, CH₃CH₂CH₂Cl, AlCl₃
B) benzene, CH₃CH?CH₂, HF
C) benzene,1.CH₃CH₂COCl/AlCl₃ 2.H₂O 3.NH₂NH₂/HO^-/?
D) benzene, CH₃CH₂CH₂OH, H₂SO₄
E) chlorobenzene, CH₃CH?CH₂, AlCl₃

Answer 3

benzene,1.CH₃CH₂COCl/AlCl₃ 2.H₂O 3.NH₂NH₂/HO^-/?

Question 4

Which is the preferred method for the synthesis of biphenyl?

A) a Gilman reaction
B) a Heck reaction
C) a Friedel-Crafts acylation reaction
D) a Suzuki reaction
E) all of the above

Question 5

Which set of reagents should be used to prepare benzaldehyde?

A) toluene, 1. H₂CrO₄ 2. LiAlH₄ 3. H₂O
B) toluene, 1. H₂CrO₄ 2. NaBH₄ 3. H₂O
C) toluene, 1. H₂CrO₄ 2. NaBH₄ 3. PCC
D) toluene, 1. H₂CrO₄ 2. LiAlH₄ 3. PCC
E) toluene, PCC

Question 6

What is the name of the compound shown here?

A) 1-fluoro-3-methyl-6-nitrobenzene
B) 3-fluoro-4-nitro-1-methylbenzene
C) 3-fluoro-1-methyl-1-nitrobenzene
D) 2-fluoro-1-nitro-4-methylbenzene
E) 2-fluoro-4-methyl-1-nitrobenzene

Question 7

Which of the following activates a benzene ring toward electrophilic aromatic substitution?

A)
B)
C)
D)
E)

Question 8

Which of the following is an ortho-para director?

A) ?Cl
B) ?CHO
C) ?CN
D) ?NO₂
E) none of the above

Question 9

Which compound is the major product of the following reaction?

A)
B)
C)
D)
E)

Question 10

Which of the following groups most strongly activates an aromatic ring toward Friedel-Crafts acylation?

A) ?NH₂
B) ?OCH₃
C) ?O-C(?O)CH₃
D) NO₂
E) H

Question 11

Which of the following series of reactions will give the desired product?

A)
B)
C)
D)
E)