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MCAT Ochem > Alcohols > Flashcards

Alcohols Flashcards

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MCAT flashcards
1
Q

Describe the structure of a phenol

A

A benzene ring with hydroxyl groups

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2
Q

Alcohols have high boiling points due to

A

the ability to hydrogen bond

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3
Q

Because alcohols can hydrogen bond it increases their

A

solubility and boiling points

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4
Q

Alcohols can dissociate into

A

protons (H+) and alkoxides (RO-)

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5
Q

Phenols are the most acidic alcohols because

A

the aromatic ring can delocalize the charge of the conjugate base

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6
Q

Primary alcohols can be oxidized to aldehydes by

A

Pyridinium Chlorochromate (PCC)

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7
Q

Primary alcohols can be fully oxidized to ________ by ________

A

Carboxylic Acids, strong oxidizing agents

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8
Q

Strong oxidizing agents include what ?

A

A metal bound to a lot of oxygens

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9
Q

Describe a Jones Oxidation

A

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

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10
Q

What are the functions of mesylates and tolsylates?

A

To make alcohol into a better leaving group

To protect alcohol from reacting

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11
Q

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

A

acetals or ketals, diols

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12
Q

One equivalent of alcohol reacting with an aldehyde forms a

A

hemiacetal

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13
Q

One equivalent of alcohol reacting with a ketone forms a

A

hemiketal

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14
Q

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

A

an aqueous acid, deprotection

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15
Q

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

A

geminal diols

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16
Q

What is a geminal diol

A

a molecule that is two parts alcohol

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17
Q

Describe the structure of a phenol

A

An aromatic ring with hydroxyl groups attached

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18
Q

What increases the boiling point of alcohols

A

More hydroxyl groups which are capable of hydrogen bonding

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19
Q

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

A

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

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20
Q

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

A

Pyridinium Chlorochromate, oxidizes alcohols

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21
Q

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

A

Geminal Diols

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22
Q

How are mesylates formed?

A

Using methylsplfonyl chloride and alcohol in the presence of a base

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23
Q

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

A

True

24
Q

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

A

Lithium Aluminum Hydride

25
Q

Carbonyls react strongly with _______ agents like LiAlH4

A

Reducing

26
Q

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

A

Diol, Carbonyl

27
Q

Treatment of phenols with oxidizing agents produces

A

Quinones

28
Q

Describe the structure of a quinone

A

A conjugated ring with carbonyls

29
Q

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

A

Phenols have one OH group

Hydroquinone have two OH groups

30
Q

Are quinones electrophiles or nucleophiles?

A

Electrophiles

31
Q

Quinones act as electron ________-

A

acceptors

32
Q

Oxidation of phenols forms

A

quinones

33
Q

Oxidation of Quinones forms

A

Hydroxyquinones

34
Q

Quinone structures are characterized by

A

An aromatic ring with Carbonyl groups attached

35
Q

Hydroquinones can be oxidized to_____ which can be further oxidized to________

A

Quinones, Hydroxyquinones

36
Q

How do quinones and hydroxyquinones differ?

A

The presence of a hydroxyl group on a ring

37
Q

Are electron donating molecules are electrophilic or nucleophilic?

A

Nucleophilic

38
Q

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

A

Nucleophile

39
Q

The resonance stabilization of quinones makes it an electron _______

A

donator

40
Q

What charge do nucleophiles have ?

A

Positive

41
Q

Are quinones electrophiles or nucleophiles?

A

Electrophiles

42
Q

Are quinones aromatic?

A

No

43
Q

What makes a structure aromatic?

A
  1. all atoms must be sp2 hybridized
  2. an odd number of pi electrons
  3. Planar-overlapping of pi orbitals
44
Q

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

A

Odd

45
Q

What forms a hydroxyquinone?

A

Oxidation of a Quinone, adding a hydroxyl group

—remember oxidation increases the number of bonds to oxygen, an OH group is added

46
Q

Oxidation of a quinone forms

A

a hydroxyquinone

47
Q

Oxidation of ubiquinone forms

A

Ubiquinol

48
Q

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

A

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

49
Q

What are the Huckel’s Rule ‘magic numbers’

A

2,6,10,14

50
Q

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

A

even

51
Q

Are phenols aromatic ?

A

Yes

52
Q

Describe how deprotection of a ketone or aldehyde occurs?

A

Acidic workup using a catalytic acid with water

53
Q

Tertiary alcohols are oxidized with difficulty because

A

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

54
Q

Why are the hydroxyl hydrogens on phenol acidic?

A

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

55
Q

What is used to remove a protecting group

A

A strong acid

56
Q

Why are bases good leaving groups?

A

Because they are more stable with an extra set of electrons

57
Q

What is a leaving group?

A

The molecule that keeps the electrons after heterolysis

MCAT Ochem (4 decks)

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