Substituted Effects in Electrophilic Substitution

Question 1

Ortho- and para-directing deactivators

Answer 1

EDG: Substituents causing electron to be pulled out of the benzene ring

Ex: Halogen

Question 2

Meta Directing

Answer 2

EWG: Substituents that pull electron away from the benzene ring
Ex: nitro, carbonyl compounds,

Question 3

What happens when a substituted aromatic react with KMnO4?

Answer 3

The alkyl side chain will be converted to carboxylic acid.

This will only work if side chain has a benzyllic C-H
(tert-butylbenzene will not react to KMnO4)

Question 4

What happens when a substituted aromatic react with NBS?

Answer 4

ONLY the benzylic H on the the benzylic C will be converted to a bromine.

Question 5

What happens when an aromatic is hydrogenated?

Answer 5

1. If substituted, the benzylic alkene will be reduced to a alkane

Question 6

What must be used to hydrogenate an aromatic ring?

Answer 6

1. H2, Pt/C with high pressure
2. H2, Pd/C

Question 7

What happens to the benzylic oxygen if an aromatic undergoes hydrogenation?

Answer 7

Oxygen turns into hydrogen