Alcohols

Question 1

have the general formula ROH, with the functional group -OH referred to as a hydroxyl group; named with suffix -ol, if not highest priority named as substituent with prefix hydroxy-

Answer 1

alcohol

Question 2

benzene ring with hydroxyl groups; named for relative position of hydroxyl group: ortho- (adjacent carbons), meta- (one carbon in between), or para- (opposite sides of ring); more acidic than other alcohols because aromatic ring can delocalize the charge of the conjugate base

Answer 2

phenol

Question 3

ability raises boiling and melting points of alcohols relative to corresponding alkanes, and increases solubility of alcohols

Answer 3

hydrogen bonding

Question 4

groups that decrease acidity because they destabilize negative charges, such as alkyl groups

Answer 4

EDG (electron donating group)

Question 5

groups that increase acidity because they stabilize negative charges, such as electronegative atoms and aromatic rings

Answer 5

EWG (electron withdrawing group)

Question 6

only reagent that can oxidize primary alcohols only to aldehydes, would be oxidized to carboxylic acids by any stronger oxidizing agents

Answer 6

PCC (pyridinium chlorochromate)

Question 7

oxidize primary alcohols to carboxylic acids and secondary alcohols to ketones

Answer 7

CrO3, Na2Cr2O7, or K2Cr2O7 ( chromium trioxide, sodium dichromate, or potassium dichromate)

Question 8

can be oxidized to ketones by any common oxidizing agents

Answer 8

secondary alcohols

Question 9

other forms alcohols can be converted to to make them better leaving groups for nucleophilic substitution reactions

Answer 9

mesylates and tosylates

Question 10

contain functional group -SO3CH3, derived from methanesulfonic acid

Answer 10

mesylates

Question 11

structure of a mesylate anion

Answer 11

Question 12

contain functional group -SO3C6H4CH3, derived from toluenesulfonic acid

Answer 12

tosylate

Question 13

structure of a tosylate

Answer 13

Question 14

aldehydes and ketones can be protected by being converted to ____ and ____; formed by reacting two equivalents of an alcohol or a diol with a carbonyl

Answer 14

acetals and ketals

Question 15

a primary carbon with two -OR groups and a H atom

Answer 15

acetal

Question 16

a secondary carbon with two -OR groups

Answer 16

ketal

Question 17

conversion of an acetal or ketal back to a carbonyl by catalytic acid

Answer 17

deprotection

Question 18

what is happening in the reaction towards the right

Answer 18

protection of a ketone by ketal formation using a dialcohol

Question 19

synthesized through oxidation of phenols; resonance stabilized nucleophiles

Answer 19

quinones

Question 20

vitamin K(1); biochemically relevant quinone important for photosynthesis and carboxylation of some clotting factors in the blood

Answer 20

phylloquinone

Question 21

vitamin K(2); biochemically relevant quinone

Answer 21

menaquinone

Question 22

a benzene ring with two hydroxyl groups

Answer 22

hydroquinone

Question 23

contains two carbonyls and a variable number of hydroxyl groups produced by oxidation of quinones, adding a variable number of hydroxyl groups

Answer 23

hydroxyquinone

Question 24

coenzyme Q; a biologically active quinone that acts as an electron acceptor in Complexes I, II, and III of the electron transport chain

Answer 24

ubiquinone

Question 25

ubiquinone is reduced to ____

Answer 25

ubiquinol