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Organic Chemistry Il > Alcohols, Diols, Thiols > Flashcards

Alcohols, Diols, Thiols Flashcards

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1
Q

What are alcohols ?

A

Organic compounds containing hydroxyl groups

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2
Q

What is the most common and useful compound in nature, in industry, and around the house ?

A

Alcohol

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3
Q

Ethyl alcohol was considered to be what?

A

The essence of wine

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4
Q

Where is ethyl alcohol found in?

A

Alcoholic beverages, cosmetics, and drug preparations

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5
Q

What is methyl alcohol used as ?

A

A fuel and solvent

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6
Q

What is isopropyl alcohol use for ?

A

As a skin cleanser for injections and minor cuts

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7
Q

What are alcohols with two OH groups called ?

A

Diols or glycols

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8
Q

What does the term glycol generally mean ?

A

1,2 - diol or vicinal diol

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9
Q

How are glycols usually synthesized ?

A

By the hydroxylation of alkenes, using peroxyacids, osmium tetroxide, or potassium permanganate

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10
Q

What are phenols ?

A

Compounds in which an OH group is directly attached to an aromatic ring

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11
Q

How do phenols differ from alcohols ?

A

Phenols are more acidic in water

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12
Q

What alcohols are liquid at room temperature ?

A

11 to 12 carbon atoms

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13
Q

Which alcohols are heavier but still fruity odors ?

A

Higher alcohols

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14
Q

What are the two important intermolecular forces es responsible for the boiling point of alcohols ?

A

Hydrogen bonding
Dipole-dipole attractions

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15
Q

Which is the major intermolecular attraction responsible for ethanols high boiling point ?

A

Hydrogen bonding

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16
Q

Dipole-dipole attractions also contribute to what ?

A

To the relatively high boiling points of alcohols and ethers

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17
Q

Explain the solubility of alcohols in water

A

Alcohols form hydrogen bonds with water, and several of the lower-molecular-weight alcohols are miscible with water

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18
Q

When does the water solubility of alcohol decrease?

A

When the alkyl group becomes larger

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19
Q

What is the use of methanol ?

A

Industrial solvent
Preparation of methyl ethers, methyl esters and other compounds used in plastic, medicine, fuels and solvents

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20
Q

Why is methanol most common industrial solvent ?

A

Cheap
Relatively less toxic
Dissolves a wide variety of polar and non polar substances

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21
Q

What is ethanol used for ?

A

Excellent solvent of low toxicity that is cheap to produce
Good motor fuel
Ingredient in many mouthwashes

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22
Q

What are both ethanol and propane-2-ol used for?

A

Topical antiseptic

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23
Q

How is alkoxide ion formed ?

A

By removing the hydroxyl proton from alcohol by reduction with active metal such as sodium or potassium

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24
Q

The reactivity of alcohols towards sodium and potassium decreases in what order ?

A

Methyl
Primary
Secondary
Tertiary

25
Q

Sodium reacts quickly with what ?

A

Primary alcohols and some secondary alcohols

26
Q

What reacts quickly with tertiary alcohols and some secondary?

A

Potassium, as it is more reactive than sodium

27
Q

What is more acidic phenol or cyclohexanol ?

A

Phenol

28
Q

Why is phenol acidic ?

A
29
Q

What was phenol once called “

A

Carbolic acid because of its stability to neutralize common bases

30
Q

What is phenol used as ?

A

Antiseptic agent

31
Q

What are grignards reagents ?

A

Strong nucleophiles and strong bases

32
Q

What is the most useful nucleophilic reaction of Grignard reagents ?

A

Additions to carbonyl groups

33
Q

Grignards reagents first adds to what ?

A

Ketones, aldehydes, formaldehyde to form an alkoxide ion

34
Q

How is alkoxide ion turned into alcohol ?

A

Additional of dilute acid

35
Q

How is primary alcohol formed ?

A

By addition of Grignard reagent to a formaldehyde, followed by protonation

36
Q
A

Formation of primary alcohols

37
Q

How are secondary alcohols formed ?

A

By addition of Grignard reagent to an aldehyde in ether, followed by protonation

38
Q
A

Formation of secondary alcohols

39
Q

How are tertiary alcohols formed ?

A

By addition of Grignard reagent to ketones, followed by protonation

40
Q
A

Formation of tertiary alcohol

41
Q

Oxidation of primary alcohols leads to what ?

A

Aldehyde and further oxidation leads to acid

42
Q

Secondary alcohols are oxidized to what ?

A

Ketones

43
Q

Tertiary alcohols are oxidized to what “

A

They can’t be oxidized

44
Q
A

Oxidation of primary alcohols

45
Q

What acid is used for oxidation if secondary alcohols ?

A

Chromic acid reagent

46
Q
A

Oxidation of secondary alcohols

47
Q

Why are tertiary alcohols resistant to oxidation ?

A

Tertiary alcohols don’t have hydrogen atoms so a carbon-carbon bond needs to be broken which requires severe conditions

48
Q

Alcohols are reduced to what ?

A

Alkanes

49
Q

Why is reduction of alcohols rare?

A

Because it removes a functional group, leaving fewer options for further reactions

50
Q

What are the steps to reduce alcohol ?

A

By dehydration to an Alkene, then hydrogenating the Alkene

51
Q
A

Reduction of alcohols

52
Q

What is bimolecular dehydration of alcohols?

A

Type of condensation that joins two or more molecules often with the loss of a small molecule like water

53
Q

What is bimolecular dehydration of alcohol used for ?

A

For the industrial synthesis of diethyl ether and dimethyl ether

54
Q

What are the two reactions included in bimolecular dehydration ?

A

Elimination, substitution

55
Q

How to get a carboxylic ester ?

A

Replacing the OH group of a carboxylic acid with the OR group of an alcohol

56
Q
A

Fischer esterification

57
Q

What is the application of ester as drugs ?

A
58
Q

What is the application of alcohols in metabolism of drugs ?

A

Organic Chemistry Il (12 decks)

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