5 Alcohols

Question 1

IUPAC nomenclature

when alcohol is the highest priority group

Answer 1

“-ol”

Question 2

IUPAC nomenclature

when alcohol is not the highest priority group

Answer 2

“hydroxy-“

Question 3

common name

Answer 3

alkyl group + “alcohol”

Question 4

IUPAC nomenclature for aromatic alcohols

Answer 4

“phenols”

Question 5

intermolecular hydrogen bonding

Answer 5

increases solubility in water
increases melting point
increases boiling point

increasing hydroxyl groups increases degrees of hydrogen bonding

Question 6

electron-donating groups

Answer 6

destablizes alkoxide anion
e.g. alkyl groups
decrease acidity

Question 7

resonance/electron-withdrawing groups

Answer 7

stabilizes alkoxide anion

increases acidity

Question 8

oxidation of primary alcohol to aldehyde

Answer 8

PCC

Question 9

oxidation of secondary alcohol to ketone

Answer 9

dichromate salt

Na2Cr2O7
H2SO4

Question 10

Jones oxidation (primary alcohol –> CO2)

Answer 10

CrO3, H2SO4

acetone

Question 11

(-SO3CH3)

Answer 11

mesylate

methylsulfonil chloride + alcohol in presence of base

Question 12

(-SO3C6H4CH3)

Answer 12

tosylate

alcohol + p-toluenesulfonic acid

Question 13

protecting groups for aldehydes and ketones

Answer 13

aldehyde/ketone + 2 eq. of alcohol OR diol

–> acetal/ketal

Question 14

acetals

Answer 14

primary carbons with two -OR groups and a hydrogen atom

Question 15

ketals

Answer 15

secondary carbon with two -OR groups

Question 16

deprotection

Answer 16

acetal/ketal + aq. acid –> carbonyl (unprotected)

Question 17

quinones

Answer 17

treatment of phenols with oxidizing agents

Question 18

hydroxyquinones

Answer 18

same ring and carbonyl backbone structure of quinones

ADD >= 1 hydroxyl group

Question 19

ubiquinone

Answer 19

“coenzyme Q”

biologically active quinone
electron carrier (Complex I, II, III of ETC)
lipid soluble (long alkyl chain) within phospholipid bilayer

reduces to ubiquinol upon electron acceptance