Chapter #5

Question 1

antiseptic

Answer 1

relating to or denoting substances that prevent the growth of disease-causing microorganisms.

Question 2

what functional groups do alcohols have?

Answer 2

hydroxy (OH-)

Question 3

phenol

Answer 3

aromatic 6 carbon ring with hydroxyl group attached to it

Question 4

ortho-, meta-, para-

Answer 4

ortho: two groups on adjacent carbons
meta: two groups separated by one carbon
para: two groups on opposite sides of the ring

Question 5

what makes phenols so acidic?

Answer 5

the resonance between the ring and the lone pairs on the oxygen of the hydroxyl group

Question 6

boiling point _____ with more hydroxyl groups due to ____

Answer 6

increases

increased hydrogen bonding

Question 7

describe the hydrogen bond

Answer 7

extreme polarity in bonds leads to partial positive and partial negative charges on atoms that then electrostatically attract other atoms from different molecules (going through the same thing)

Question 8

strong acids have ___ Ka values and ____ pKa values

Answer 8

large Ka

small pKa

Question 9

electron donating groups ____ acidity while electron withdrawing groups ____ acidity

Answer 9

decrease

increase

Question 10

discuss acidity and more alkyl groups

Answer 10

more alkyl groups decrease acidity because they increase electron density which destabilizes the negative charge that comes with hydrogen leaving.

Question 11

does 1-hexanol or 1-pentanol have a higher boiling point?

Answer 11

1-hexonol due to increase van der waals forces

Question 12

what is the reagent used to oxidize primary alcohols to aldehydes (and stop there)

Answer 12

PCC

CrO3/Pyridine

Question 13

what does PCC stand for?

Answer 13

pyridinium cholorochromate

Question 14

can all alcohols be oxidized?

Answer 14

no, tertiary alcohols cannot be oxidized because they are already as oxidized as they can be without breaking a carbon-carbon bond.

Question 15

what is involved in the jones oxidation?

Answer 15

CrO3, H2SO4, and acetone
primary alcohols to carboxylic acids
secondary alcohols to ketones

Question 16

how can hydroxyl groups be reacted to form better leaving groups?

Answer 16

can be protonated or reacted to from better leaving groups called mesylates and tosylates

Question 17

what does a mesylate contain?

Answer 17

-SO3CH3

Question 18

what is mesylate derived from and how is it prepared?

Answer 18

derived from methanesulfonic acid

prepared using methylsulfonyl chloride and an alcohol in the presence of a base

Question 19

what does tosylate contain?

Answer 19

-SO3C6H4CH3

Question 20

what is tosylate derived from?

Answer 20

toluenesulfonic acid

Question 21

in addition to making -OH a better leaving group, what else do mesylates and tosylates do?

Answer 21

they can protect the alcohol from being reacted with.

Question 22

what are diols used to protect?

Answer 22

use to protect ketone or aldehyde carbonyl carbon from attack

Question 23

how do you remove protection via acetal or ketal group?

Answer 23

aqueous acid

Question 24

what is another alternative to using a diol to protect a ketone or aldehyde?

Answer 24

using 2 equivalents of alcohols

Question 25

how do mesylates and tosylates protect alcohols from being reacted with?

Answer 25

many of the oxidizing agents that react with alcohols do not react with mesylates and tosylates

Question 26

why does formation of acetal or ketal protect aldehydes and ketones?

Answer 26

they are less reactive

Question 27

how do you name quinones?

Answer 27

indicating the position of the carbonyls numerically and adding quinone to the name of the parent phenol

Question 28

what is another name for phylloquinone

Answer 28

vitamin K1

Question 29

what class of molecules is vitamin K2 a part of?

Answer 29

menaquinones

Question 30

compare hydroquinones and hydroxyquinones

Answer 30

hydroquinone is a benzene ring with two hydroxyl groups | hydroxyquinone contains two carbonyls and a variable number of hydroxyl groups.

Question 31

what is another name for ubiquinone

Answer 31

coenzyme Q

Question 32

what happens when ubiquinone is reduced?

Answer 32

turns into ubiquinol

Question 33

what are the vitamin Ks invovled in

Answer 33

blood coagulation

Question 34

what is ubiquinone involved in?

Answer 34

electron transport chain

Question 35

what allows ubiquinone to function?

Answer 35

it has a long alkyl chain which allows it to move throughout the phospholipid bilayer, carrying electrons. able to carry the electrons by distributing the charge throughout its conjugated ring.

Question 36

how do hydroxyquinones and quinones differ?

Answer 36

hydroxyquinones have a variable addition of -OH groups.

Question 37

discuss hydrogen bonding and solubility

Answer 37

hydrogen bonding increases the solubility of molecules

Question 38

Is the H in hexanol or cyclohexanol more acidic?

Answer 38

hexanol because the ring structure of cyclohexanol is slightly more electron donating

Question 39

can tertiary alcohols be oxidized?

Answer 39

yes, but only under extreme conditions

Question 40

how to name diols

Answer 40

parent name, location of hydroxyls indiacted, ends with "-diol"

Question 41

why do phenols have more acidic hydroxyl hydrogens?

Answer 41

resonance stabilization of the conjugate base.

Question 42

is jones oxidation performed in aqueous or anhydrous conditions?

Answer 42

aqueous

Question 43

how to go from acetal to carbonyl and dialcohol?

Answer 43

aqueous acid | deprotection

Question 44

how many oxidation steps to go from phenol to hydroxyquinone?

Answer 44

2 phenol ==> quinone quinone==> hydroxyquinone