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Question 1

Benzene ->
Reagent: bromonium ion Br+
[Br2, FeBr3]

Answer 1

Benzene-Br

Question 2

Benzene ->
Reagent: O = N+ = O Nitronium ion
[HNO3, H2SO4]

Answer 2

Benzene-NO2

Question 3

Benzene ->
Reagent: S+ bound to 2 =O and 1 -OH (sulfonium ion)
[H2SO4, SO3]

Answer 3

Benzene-SO3H

Question 4

Benzene ->
Reagents: Cl2, FeCl3

Answer 4

Benzene-Cl

Question 5

What does benzene act as in Electrophilic Aromatic Substitution Reaction?

Answer 5

Nucleophile

Question 6

Benzene ->
Reagents: CH3Cl, AlCl3
[CH3+]
What is the product? What is this reaction called? Which side is more nucleophilic?

Answer 6

Benzene-CH3
Friedel-Crafts Alkylation
Products more nucleophilic, more reaction

Question 7

Disadvantages of Friedel-Crafts alkylation

Answer 7

1) multiple alkylation (ignore in exam or HW)
2) does not work on benzene-Y where Y is an EWG
3) Carbocation Rearrangement

Question 8

Benzene + isobutyl-Cl ->
Reagent: AlCl3

Answer 8

1,2 hydrogen shift of carbocation on isobutyl to center carbon
Product: benzene—tert-butyl

Question 9

What does Friedel-Crafts Alkylation work on?

Answer 9

Any Haloalkane 1°, 2°, 3°