Ch. 17: Aromatic Compounds

Question 1

Oxidation Reagents (2)

Answer 1

Na2Cr2O7, H2SO4, H2O
Or 1. KMnO4, H2O, heat 2. H3O+

Question 2

What does oxidation do?

Answer 2

Substitutes carboxylic acid at benzylic position

Question 3

Substitution Reagents (2)

Answer 3

H2O, SN1 (tertiary) or NaOH, SN2 (primary)

Question 4

What does substitution do?

Answer 4

Replaces X with OH (by product of H-X)

Question 5

Free-Radical Bromination Reagent

Answer 5

NBS, heat

Question 6

What does free-radical bromination do?

Answer 6

Adds Br to alpha-hydrogens

Question 7

Elimination Reagents (2)

Answer 7

Conc. H2SO4, E1 (for OH)
or NaOEt, E2 (for Br)

Question 8

What does elimination reaction do?

Answer 8

Eliminates the “R” group and CH3, replaces with a double C-C bond

Question 9

Catalytic Hydrogenation Reagent

Answer 9

Ni, 100 atm, 150C

Question 10

What does catalytic hydrogenation do?

Answer 10

Removes all double bonds from benzene ring, leaving a cyclohexane

Question 11

Birch Reduction Reagent

Answer 11

Na, CH3OH, NH3

Question 12

What does birch reduction do?

Answer 12

Reduces benzene ring to two parallel double bonds (non-conjugated diene)

Question 13

Aromatic compounds

Answer 13

Are derivatives of benzene

Question 14

Phenyl group

Answer 14

When a benzene ring is a substituent

Question 15

Requirements for aromaticity

Answer 15

• Cyclic & Planar
• Continuous p-system (conjugated)
• 4n + 2 (Huckel’s rule)

Question 16

Annulene exception to aromaticity

Answer 16

Annuleren is fully conjugated but steric interaction makes it nonaromatic

Question 17

Heterocycles

Answer 17

Cyclic compounds containing heteroatom (S, N, O)

Question 18

How do you name a poly-substituted benzene?

Answer 18

Use common names for parent chain, and make others substituents

Question 19

Common name: Toluene

Answer 19

Benzene ring with CH3

Question 20

Common name: Phenol

Answer 20

Benzene ring with -OH

Question 21

Common name: Benzoic Acid

Answer 21

Benzene ring with carboxylic acid

Question 22

Common name: Benzaldehyde

Answer 22

Benzene ring with aldehyde

Question 23

Common name: Anisole

Answer 23

Benzene ring with OCH3

Question 24

Common name: Benzenesulfonic acid

Answer 24

Benzene ring with SO3H

Question 25

Common name: Acetophenone

Answer 25

Benzene ring with ketone

Question 26

Common name: Styrene

Answer 26

Benzene ring with CH=CH2 (double bond)