Question 1

Aromatic rings only undergo reactions by ___ . The mechanism of this reaction produces an intermediate similar to the one found in the ___ mechanism from Chapter 8. The carbocation is then removed through elimination to reform the aromatic ring.

A) S_N2, S_N1
B) EAS, S_N2
C) S_N2, addition
D) EAS, addition

EAS, addition

Accepted Answer

Aromatic rings undergo Electrophilic Aromatic Substitution (EAS) reactions, which involve an addition intermediate similar to those in addition reactions.

Question 2

What is the product of the following reaction?  &#10;A) I&#10;B) II&#10;C) III&#10;D) IV

Accepted Answer

Halogenation of the benzene occurs through electrophilic aromatic substitution

Question 3

What is the product of the following reaction?  &#10;A) I&#10;B) II&#10;C) III&#10;D) IV

Accepted Answer

Nitration of the benzene ring through electrophilic aromatic substitution.

Question 4

What is the product of the following reaction (assume no rearrangements)?  &#10;A) I&#10;B) II&#10;C) III&#10;D) IV

Accepted Answer

This is a Friedel-Crafts alkylation.

Question 5

What is the product of the following reaction?  &#10;A) I&#10;B) II&#10;C) III&#10;D) IV

Accepted Answer

Para position is blocked. This is a Friedel-Crafts acylation followed by a Clemmensen Reduction at the ortho position.

Question 6

What is the product of the following reaction?  &#10;A) I&#10;B) II&#10;C) III&#10;D) IV

Accepted Answer

Polynitration leads to trinitrotoluene, TNT.

Question 7

What is the major product of the following reaction?  &#10;A) I&#10;B) II&#10;C) III&#10;D) IV

Accepted Answer

Para bromination favored.

Question 8

What is the correct order of reagents to achieve the following synthesis? A) NBS, light, CCl₄ B) 1) Zn(Hg), HCl reflux 2) NBS, light, CCl₄ C) CH₃MgBr D) HBr

Accepted Answer

The ketone is first reduced with the Clemmensen reduction, then the side chain is halogenated through radical halogenation.

Question 9

What is the correct order of reagents to achieve the following synthesis? A) 1) HNO₃/H₂SO₄ 2) Zn(Hg), HCl reflux 3) KMnO₄, OH^-, heat 4) H⁺ B) 1) KMnO₄, OH^-, heat 2) H⁺2) HNO₃/H₂SO₄ C) 1) LiAlH₄ 2) H⁺ 3) NaH, Ts-Cl 3) Sodium Methoxide, methanol 5) KMnO₄, OH^-, heat 6) H⁺2) HNO₃/H₂SO₄ D) all of the above

Accepted Answer

All three give the correct answer.

Question 10

What is the correct order of reagents to achieve the following synthesis? A) 1) Br₂/FeBr₃ (twice) 2) HNO₃/H₂SO₄ B) 1) CH₃COCl, NaOH 2) H₂SO₄(conc.) 3) Br₂/FeBr₃ (twice) 4) H₂SO₄, H₂O, heat 5) OH^- 6) HNO₃/H₂SO₄ C) 1) CH₃COCl, NaOH 2) Br₂/FeBr₃ (twice) 3) H₂SO₄(conc.) 4) HNO₃/H₂SO₄5) H₂SO₄, H₂O, heat 6) OH^- D) 1) CH₃COCl, NaOH 2) Br₂/FeBr₃ (twice) 3) HNO₃/H₂SO₄

Accepted Answer

Response A: Polybrominations at all three positions are possible. Para bromination will occur before ortho. This will leave only an ortho position available for the nitro group. Response B: CORRECT! Response C: 1^st step is correct. But bromine will go para in the second step and not give the proper product. Response D: 1^st step is correct. But bromine will go para in the second step and not give the proper product.

Deck 15: Reactions of Aromatic Compounds