Ch. 18: Aromatic Substitution Rxns

Question 1

Bromination reagent (Electrophilic)

Answer 1

Br2, AlBr3

Question 2

What does bromination do?

Answer 2

Adds -Br to benzene

Question 3

Chlorination reagent

Answer 3

Cl2, AlCl3

Question 4

What does chlorination do?

Answer 4

Adds -Cl to benzene

Question 5

Nitration reagent

Answer 5

HNO3, H2SO4

Question 6

What does nitration do?

Answer 6

Adds -NO2 to benzene

Question 7

Sulfonation reagent

Answer 7

Fuming H2SO4

Question 8

Desulfonation reagent

Answer 8

Dilute H2SO4

Question 9

What does sulfonation do?

Answer 9

Adds -SO3H to benzene

Question 10

FC Alkylation reagent

Answer 10

R-Cl, AlCl3

Question 11

What does alkylation do?

Answer 11

Adds R group to benzene

Question 12

FC Acylation reagent

Answer 12

Acyl-Cl, AlCl3

Question 13

What does acylation do?

Answer 13

Adds Acyl group (R-C=O) to benzene

Question 14

Nitration reduction reagent

Answer 14

1. Fe or Zn, HCl
2. NaOH

Question 15

What does nitration reduction do?

Answer 15

Reduces -NO2 to -NH2

Question 16

Benzylic bromination reagent

Answer 16

XS NBS

Question 17

What does benzylic bromination do?

Answer 17

Brominates -CH3 to -CBr3 (all available H change to Br)

Question 18

Oxidation reagent

Answer 18

1. KMnO4, H2O, heat
2. H3O+

Question 19

What does oxidation do?

Answer 19

Replaces -CH3 with -COOH (carboxylic acid)

Question 20

Clemmensen reduction reagent

Answer 20

Zn(Hg), HCl, heat

Question 21

What does clemmensen reduction do?

Answer 21

Reduces O= to H (double bond oxygen)

Question 22

Nucleophilic aromatic substitution reagent

Answer 22

1. NaOH, 70C
2. H3O+

Question 23

What does nucleophilic aromatic substitution do?

Answer 23

replaces -Br (X) with -OH

Question 24

Elimination addition reagents (2)

Answer 24

1. NaOH, 350C 2. H3O+
   or 1. NaNH2, NH3 2. H3O+

Question 25

What does elimination addition do?

Answer 25

Replaces -Cl with -OH or -NH2 (whichever is after Na in the reagent)

Question 26

Strong activators

Answer 26

Characterized by the presence of l.p. immediate adjacent to the aromatic ring; O/P directing

Question 27

Moderate activators

Answer 27

Exhibit l.p. that is already delocalized outside of the ring

Question 28

Activators examples

Answer 28

Alkyl, OH/R, CH3, ester, amide

Question 29

Moderate deactivator

Answer 29

Exhibit a conjugated pi bond to an electronegative atom

Question 30

Strong deactivator

Answer 30

Powerfully electron withdrawing via resonance/induction

Question 31

Deactivators examples

Answer 31

Halogens (direct O/P); NO2, NR3, CN, SO4H, other carboxylic acid derivatives

Question 32

Ortho

Answer 32

1,2 (minor)

Question 33

Meta

Answer 33

1,3

Question 34

Para

Answer 34

1,4 (major)