Organic Chemistry Ch 5. Alcohols

Question 1

Alcohols

Answer 1

Have the general form ROH and are named with the suffix -ol, if they are not the highest priority they were given the prefix hydroxy-, can hydrogen bond raising their boiling in mint melting points relative to corresponding alkanes, hydrogen bonding also increases solubility of alcohols

Question 2

Phenols

Answer 2

Benzene rings with a hydroxyl groups, named for the relative positions of the hydroxyl groups: ortho (adjacent carbons), meta (separated by one carbon) or para (opposite side of ring), more acidic than alcohols because the aromatic ring can delocalize the charge of the conjugate base

Question 3

Electron donating groups

Answer 3

Decrease acidity because the destabilize negative charges, include alkyl groups

Question 4

Electron withdrawing groups

Answer 4

Increase acidity because they stabilize negative charges, include electronegative atoms and aromatic rings

Question 5

Primary alcohol oxidation

Answer 5

Can be oxidized to aldehydes only by pyridinium chorochoromate (PCC), will be oxidized all the way to carboxylic acids with stronger oxidizing agents

Question 6

Pyridinium chlorochromate

Answer 6

PCC - oxidizes primary alcohols to aldehydes

Question 7

Secondary alcohol oxidation

Answer 7

Secondary alcohols can be oxidized to ketones by any common oxidizing agent

Question 8

Alcohol conversions to mesylates or tosylates

Answer 8

Alcohol can be converted to mesylates or tosylates to make them better leaving groups for nucleophilic substitution reactions

Question 9

Mesylates

Answer 9

Contain the functional group -SO3CH3, which is derived from methanesulfonic acid

Question 10

Tosylates

Answer 10

Contain the functional group -SO3C6H4CH3, which is derived from toluenesulfonic acid

Question 11

Aldehyde or ketone protection via acetals or ketals

Answer 11

Two equivalents of alcohol or a dialcohol are reacted with the carbonyl to form an acetal or ketal, allows for other functional groups to be reacted (esp by reduction) without effect on the newly formed acetal or metal), can be converted ack to the carbonyl via catalytic acid

Question 12

Acetal

Answer 12

A primary carbon with two -OR groups and a hydrogen atom

Question 13

Ketal

Answer 13

Secondary carbon with two -OR groups

Question 14

Deprotection

Answer 14

When an acetal or ketal is converted back to a carbonyl using catalytic acid

Question 15

Quinones

Answer 15

Synthesized through oxidation of phenols, are resonance stabilized electrophiles, include vitamin K1 and K2

Question 16

Phylloquinone

Answer 16

Vitamin K1

Question 17

Menaquinone

Answer 17

Vitamin K2

Question 18

Hydroxyquinones

Answer 18

Produced by oxidation of quinones, adding a variable number of hydroxyl groups

Question 19

Ubiquinone

Answer 19

aka coenzyme Q - another biologically active quinone that acts as an electron accept in complexes I, II, and II of the ETC, reduced to ubiquinol