Ch 16 Benzene Derivatives

Question 1

electrophilic aromatic substitution

Fluorination

Answer 1

F–N–N–CH2Cl, (F-TEDA-BF4)

(6 sided ring with the nitrogens)

Adds F group on the ring

Question 2

electrophilic aromatic substitution

bromination

Answer 2

Br2, FeBr3

Adds Br to the ring

HBr = byproduct

Question 3

electrophilic aromatic substitution

Chlorination

Answer 3

Cl2, FeCl3

Adds Cl to the ring

HCl = byproduct

Question 4

electrophilic aromatic substitution

Iodination

Answer 4

I2, CuCl2

Adds an I to the ring

HI = byproduct

Question 5

electrophilic aromatic substitution

Nitration

Answer 5

HNO3, H2SO4

Adds NO2 to the ring

H2O is the byproduct

Question 6

electrophilic aromatic substitution

Sulfonation

Answer 6

SO3,H2SO4

Adds an SO3 to the ring

Question 7

electrophilic aromatic substitution

Friedel-Crafts alkylation

Answer 7

CH3Cl, AlCl3

Add an alkyl group (R) to the ring

The aromatic ring must be at least as reactive as a halobenzene. The alkyl halide must be a primary alkyl halide to undergo carbocation rearrangement.

Question 8

electrophilic aromatic substitution

Friedel-Crafts acylation

Answer 8

CH3C=OCl, AlCl3

*Cl bonded to the C

Adds C dbl bnd O CH3

HCl is the byproduct

Question 9

Reduction of aromatic nitro groups

Answer 9

1) Fe, H2SO4/ 2) NaOH

NO2 – NH2

Question 10

Nucleophillic aromatic substitution by addition to activated aryl halides

Answer 10

NaOH, H2O

Question 11

Oxidation of alkylbenzene side chain

Answer 11

KMnO4, H2O

Question 12

Benzylic bromination of alkylbenzene side chain

Answer 12

See Handout (5-sided ring N bonded Br, 2 dbl bond O)/BzO2, CCl4

Question 13

Catalytic hydrogenation of aromatic ring

Answer 13

H2, Rh/C catalyst

Question 14

Reduction of aryl alkyl ketones

Answer 14

h2/Pd, ethanol