Chapter 5

Question 1

phenols

Answer 1

alcohol in aromatic ring

very acidic due to lp on oxygen and resonance

Question 2

phenol orientation

Answer 2

Ortho- adjacent
meta- 1 C in between
para- opposite

Question 3

Hydrogen bond

Answer 3

hydrogen on very EN atom (F,O,N)

extreme polarity

Question 4

EWG and EDG affect on acidity

Answer 4

EWG increases, EDG decreases acidity by destabilizing negative charge

Question 5

oxidation

Answer 5

PCC

Chromium (Na/KCrO7) is stronger (C. ACID)

Question 6

Jones oxidation

Answer 6

CrO3, H2SO4, acetone

forms carboxylic acid and ketones

Question 7

mestylate and tosylate

Answer 7

pronates hydroxyl to make good LG for nucleophilic attack

can also protect hydroxyl from reacting with oxidation agent

Question 8

protecting groups

Answer 8

ald/ketone can react with diol to form acetal or ketal

acetals and ketals dont react with reducing agents, use aqueous acid to deprotect

Question 9

acetal vs. ketal

Answer 9

acetals is primary carbon with 2 OR, R and H

ketal is secondary carbon with 2 OR and 2R

Question 10

quinone

Answer 10

oxidized hydroquinone

resonance stabilized electrophile and electron acceptor in ETC

Question 11

hydroquinione vs. hydroxyquinone

Answer 11

benzene with 2 OH

hydroxy has 2 carbonyls and no OH

Question 12

ubiquinone

Answer 12

coenzyme Q, electron carrier in ETC