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Medical Chem (Organic chemistry) > 31. Alcohols, enols, phenols > Flashcards

31. Alcohols, enols, phenols Flashcards

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1
Q

Name of this compound

A

Alcohol

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2
Q

Name of this compound

A

Phenols

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3
Q

Name

A

enol

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4
Q

Examples of 3 hydroxyl compounds

A

Alcohols
Phenols
Enol

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5
Q

Name

A

Ethers

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6
Q

name

A

Aldehydes

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7
Q

name

A

ketones

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8
Q

How can we classify alcohols?

A
  1. Number of OH-group

2. according to the carbon harbouring the hydroxyl group

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9
Q

Classification of alcohols according to number of OH

A
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10
Q

Classify these alcohols according to number of OH- group

A

Monohydric

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11
Q

Classify these alcohols according to number of OH- group

A

Dihydric

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12
Q

Classify these alcohols according to number of OH- group

A

trihydric

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13
Q

Classify these alcohols according to number of OH- group

A

polyhydric

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14
Q

Classify these alcohols according to the carbon harbouring the hydroxyl group

A

Primary

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15
Q

Classify these alcohols according to the carbon harbouring the hydroxyl group

A

tertiary

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16
Q

2 examples of Biologically important alcohols

A
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17
Q

Physico-chemical properties of alcohols

A

Due to H-bonds, alcohols have far higher boiling points than the corresponding alkanes and alkyl halides

Alcohols form aggregates stabilized by multiple H-bonds -> Di- and polyhydric alcohols are even better soluble and have higher boiling points

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18
Q

Acid-base properties of alcohols

A

Alcohols are very weak acids (weaker than water)

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19
Q

Name of this reaction? What does it use for?

A

Water addition onto alkenes (AE)

-> synthesis of alcohol

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20
Q

Name of this reaction? What does it use for?

A

Catalytic reduction of oxo compounds

aldehydes -> primary alcohols

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21
Q

Name of this reaction? What does it use for?

A

Catalytic reduction of oxo compounds

ketones -> secondary alcohols

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22
Q

Name of this reaction? What does it use for?

A

Synthesis of alcohols by hydrolysis of esters

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23
Q

Name of this reaction? What does it use for?

A

Synthesis of alcohols by hydrolysis of ethers

24
Q

Name of this reaction? What does it use for?

A

Synthesis of alcohols by nucleophilic substitution of alkyl halides with hydroxide ions

25
Q

5 reactions that can be use to synthesize alcohols

A
  1. Water addition onto alkenes (AE)
  2. Catalytic reduction of oxo compounds
    (aldehydes -> primary alcohols; ketones -> secondary alcohols)
  3. by hydrolysis of esters
  4. by hydrolysis of ethers
  5. by nucleophilic substitution of alkyl halides with hydroxide ions
26
Q

Name of t his reaction

A

Alcoholic fermentation (alcoholic spirits)

27
Q

5 chemical reactions with starting materials are alcohols

A

• Combustion – yields CO2 and H2O
• Oxidation – produces aldehyde or ketone and carboxylic
acid
• Dehydration (elimination of water – intramolecular) – yields an alkene
• Dehydration (loss of water – intermolecular) – makes an ether
• Formation of esters, hemiacetales and acetales

28
Q

What is Combustion of alcohols?

A

Any organic molecule – including alcohols - can undergo a combustion (full oxidation) reaction, producing CO2 and H2O as common oxidation end products:

29
Q

What does oxidation of primary alcohol yield?

A
30
Q

What does oxidation of secondary alcohol yield?

A
31
Q

What does oxidation of tertiary alcohol yield?

A
32
Q

How to form formic acid?

A
33
Q

What is Intramolecular dehydration?

A

a water molecule is eliminated
from a single alcohol molecule
-> Loss of the OH group and a H-atom from the adjacent C- atom

34
Q

What is Zaitsev’s rule?

A

Zaitsev’s rule for alcohol dehydrations:

for cases where more than one alkene product might be formed from an elimination reaction
-> the hydrogen atom tends to be removed from the carbon that already possesses the fewest hydrogens

35
Q

Describe Dehydration of alcohols – synthesis of ethers

A

When lower temperatures are used than those that yield alkenes, intermolecular loss of water occurs, producing ethers

36
Q

Name of this reaction

A

keto-enol-tautomerism

37
Q

Purpose of keto-enol-tautomerism

A

Keto form is far more stable than its enol counterpart

38
Q

What are phenols?

A

The carbon atom harbouring the OH-group is part of an aromatic ring (sp2 hybridized)

39
Q

Classify these alcohols according to the number of OH- group

A

monohydric

40
Q

Classify these alcohols according to the number of OH- group

A

di- and polyhydric

41
Q

Some naturally occurring phenols

A

tyrosine - an amino acid

epinephrine - a stress hormone

42
Q

Is alcohols a stronger acid than phenol? Why?

A

NO!
Phenols are stronger acids than alcohols
-> dueto resonance stabilization of the phenoxide (phenolate) anion

43
Q

NAME OF THIS REACTION

A

Reversible oxidation of hydroquinone yields 1,4- benzoquinone, a non-aromatic compound

44
Q

What are ethers?

A

organic compounds in which two saturated carbon atoms are bound through a single oxygen atom

45
Q

name

A

diethyl ether

46
Q

NAME

A

ethyl isopropyl ether

47
Q

Name

A

methyl propyl ether

48
Q

Physico-chemical properties of ethers

-> Compare the boiling points of ethers to alkanes and alcohols

A

Compared with alkanes of similar molar mass, ethers have a similar boiling point.

Compared to an alcohol of the same molar mass, the ether will have a much lower boiling point

49
Q

Physico-chemical properties of ethers

-> compare solubility of ethers to alkanes

A

Ethers are more water-soluble than alkanes, because water molecules can H-bond with them

50
Q

Physico-chemical properties of ethers

-> compare solubility of ethers to alcohols

A

An ether and an alcohol of the same molar mass have about the same solubility in water.

51
Q

Some important chemical properties of ethers

A
  1. Highly flammable
  2. High vapor pressure
  3. Reacts with O2 to form hydroperoxides and peroxides (unstable compounds which can explode)
52
Q

Name

A

a hydroperoxide

53
Q

Name

A

a peroxide

54
Q

What are cyclic ethers?

A

The oxygen atom is part of a non-aromatic ring backbone

55
Q

name

A

Ethylene oxide

-> an epoxide

56
Q

The role of Lipid epoxides and peroxides?

A

Lipid epoxides and peroxides emerge upon exposition of plasma membranes to oxidative stress

Medical Chem (Organic chemistry) (7 decks)

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