Alcohols

Question 1

Describe the structure of a phenol

Answer 1

A benzene ring with hydroxyl groups

Question 2

Alcohols have high boiling points due to

Answer 2

the ability to hydrogen bond

Question 3

Because alcohols can hydrogen bond it increases their

Answer 3

solubility and boiling points

Question 4

Alcohols can dissociate into

Answer 4

protons (H+) and alkoxides (RO-)

Question 5

Phenols are the most acidic alcohols because

Answer 5

the aromatic ring can delocalize the charge of the conjugate base

Question 6

Primary alcohols can be oxidized to aldehydes by

Answer 6

Pyridinium Chlorochromate (PCC)

Question 7

Primary alcohols can be fully oxidized to ________ by ________

Answer 7

Carboxylic Acids, strong oxidizing agents

Question 8

Strong oxidizing agents include what ?

Answer 8

A metal bound to a lot of oxygens

Question 9

Describe a Jones Oxidation

Answer 9

When chromium trioxide is dissolved with dilute sulfuric acid in acetone to oxidize primary alcohols to carboxylic acids and secondary alcohols to ketones

Question 10

What are the functions of mesylates and tolsylates?

Answer 10

To make alcohol into a better leaving group

To protect alcohol from reacting

Question 11

Aldehydes and ketones can be protected by converting them into ______ or ______ using________

Answer 11

acetals or ketals, diols

Question 12

One equivalent of alcohol reacting with an aldehyde forms a

Answer 12

hemiacetal

Question 13

One equivalent of alcohol reacting with a ketone forms a

Answer 13

hemiketal

Question 14

An acetal or ketal can be reverted back to an aldehyde or ketone (carbonyl) by

Answer 14

an aqueous acid, deprotection

Question 15

In the presence of water and oxidizing agents, aldehydes and ketones form

Answer 15

geminal diols

Question 16

What is a geminal diol

Answer 16

a molecule that is two parts alcohol

Question 17

Describe the structure of a phenol

Answer 17

An aromatic ring with hydroxyl groups attached

Question 18

What increases the boiling point of alcohols

Answer 18

More hydroxyl groups which are capable of hydrogen bonding

Question 19

Why does p-ethylphenol have a lower pKa than ethanol?

Answer 19

p-ethylphenol has a ring structure making it resonance stabilized so its a stronger acid

Question 20

What is PCC in organic chemistry? What is it used for?

Answer 20

Pyridinium Chlorochromate, oxidizes alcohols

Question 21

Aldehydes are rapidly hydrated to form______ that can be oxidized to carboxylic acids?

Answer 21

Geminal Diols

Question 22

How are mesylates formed?

Answer 22

Using methylsplfonyl chloride and alcohol in the presence of a base

Question 23

T/F Hydroxyl groups of alcohols are poor leaving groups for nucleophilic substitution reactions

Answer 23

True

Question 24

Acetals and Ketals protect aldehydes and ketones from reacting because they do not react with

Answer 24

Lithium Aluminum Hydride

Question 25

Carbonyls react strongly with _______ agents like LiAlH4

Answer 25

Reducing

Question 26

By reacting a ______ with a ketone or aldehyde it protects that group from reacting with a reducing agent because LiAlH4 reacts strongly with _____

Answer 26

Diol, Carbonyl

Question 27

Treatment of phenols with oxidizing agents produces

Answer 27

Quinones

Question 28

Describe the structure of a quinone

Answer 28

A conjugated ring with carbonyls

Question 29

What is the difference in structure between a phenol and a hydroquinone

Answer 29

Phenols have one OH group | Hydroquinone have two OH groups

Question 30

Are quinones electrophiles or nucleophiles?

Answer 30

Electrophiles

Question 31

Quinones act as electron ________-

Answer 31

acceptors

Question 32

Oxidation of phenols forms

Answer 32

quinones

Question 33

Oxidation of Quinones forms

Answer 33

Hydroxyquinones

Question 34

Quinone structures are characterized by

Answer 34

An aromatic ring with Carbonyl groups attached

Question 35

Hydroquinones can be oxidized to_____ which can be further oxidized to________

Answer 35

Quinones, Hydroxyquinones

Question 36

How do quinones and hydroxyquinones differ?

Answer 36

The presence of a hydroxyl group on a ring

Question 37

Are electron donating molecules are electrophilic or nucleophilic?

Answer 37

Nucleophilic

Question 38

If a molecule is electron donating is it a nucleophile or electrophile?

Answer 38

Nucleophile

Question 39

The resonance stabilization of quinones makes it an electron _______

Answer 39

donator

Question 40

What charge do nucleophiles have ?

Answer 40

Positive

Question 41

Are quinones electrophiles or nucleophiles?

Answer 41

Electrophiles

Question 42

Are quinones aromatic?

Answer 42

No

Question 43

What makes a structure aromatic?

Answer 43

1. all atoms must be sp2 hybridized 2. an odd number of pi electrons 3. Planar-overlapping of pi orbitals

Question 44

For a structure to be aromatic it must have an ____ number of pi electrons

Answer 44

Odd

Question 45

What forms a hydroxyquinone?

Answer 45

Oxidation of a Quinone, adding a hydroxyl group | ---remember oxidation increases the number of bonds to oxygen, an OH group is added

Question 46

Oxidation of a quinone forms

Answer 46

a hydroxyquinone

Question 47

Oxidation of ubiquinone forms

Answer 47

Ubiquinol

Question 48

What characteristic of ubiquinol and ubiquininone allows it to act as an electron carrier in the phospholipid bilayer?

Answer 48

The long alkyl chain which is lipid soluble and hydrophobic like the FA tails

Question 49

What are the Huckel's Rule 'magic numbers'

Answer 49

2,6,10,14

Question 50

An aromatic compound has a(n) _____ number of double bonds

Answer 50

even

Question 51

Are phenols aromatic ?

Answer 51

Yes

Question 52

Describe how deprotection of a ketone or aldehyde occurs?

Answer 52

Acidic workup using a catalytic acid with water

Question 53

Tertiary alcohols are oxidized with difficulty because

Answer 53

there is no Hydrogen on the carbon containing the alcohol to be oxidized

Question 54

Why are the hydroxyl hydrogens on phenol acidic?

Answer 54

The resonance in the ring makes the Hydrogen acidic, if you move the double bonds around to the OH group the H can dissociate

Question 55

What is used to remove a protecting group

Answer 55

A strong acid

Question 56

Why are bases good leaving groups?

Answer 56

Because they are more stable with an extra set of electrons

Question 57

What is a leaving group?

Answer 57

The molecule that keeps the electrons after heterolysis