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

31. Alcohols, enols, phenols Flashcards

(56 cards)

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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?

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A

Synthesis of alcohols by hydrolysis of ethers

24
Q

Name of this reaction? What does it use for?

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A

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

25
5 reactions that can be use to synthesize alcohols
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
Name of t his reaction
Alcoholic fermentation (alcoholic spirits)
27
5 chemical reactions with starting materials are alcohols
• 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
What is Combustion of alcohols?
Any organic molecule – including alcohols - can undergo a combustion (full oxidation) reaction, producing CO2 and H2O as common oxidation end products:
29
What does oxidation of primary alcohol yield?
30
What does oxidation of secondary alcohol yield?
31
What does oxidation of tertiary alcohol yield?
32
How to form formic acid?
33
What is Intramolecular dehydration?
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
What is Zaitsev’s rule?
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
Describe Dehydration of alcohols – synthesis of ethers
When lower temperatures are used than those that yield alkenes, intermolecular loss of water occurs, producing ethers
36
Name of this reaction
keto-enol-tautomerism
37
Purpose of keto-enol-tautomerism
Keto form is far more stable than its enol counterpart
38
What are phenols?
The carbon atom harbouring the OH-group is part of an aromatic ring (sp2 hybridized)
39
Classify these alcohols according to the number of OH- group
monohydric
40
Classify these alcohols according to the number of OH- group
di- and polyhydric
41
Some naturally occurring phenols
tyrosine - an amino acid | epinephrine - a stress hormone
42
Is alcohols a stronger acid than phenol? Why?
NO! Phenols are stronger acids than alcohols -> dueto resonance stabilization of the phenoxide (phenolate) anion
43
NAME OF THIS REACTION
Reversible oxidation of hydroquinone yields 1,4- benzoquinone, a non-aromatic compound
44
What are ethers?
organic compounds in which two saturated carbon atoms are bound through a single oxygen atom
45
name
diethyl ether
46
NAME
ethyl isopropyl ether
47
Name
methyl propyl ether
48
Physico-chemical properties of ethers | -> Compare the boiling points of ethers to alkanes and alcohols
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
Physico-chemical properties of ethers | -> compare solubility of ethers to alkanes
Ethers are more water-soluble than alkanes, because water molecules can H-bond with them
50
Physico-chemical properties of ethers | -> compare solubility of ethers to alcohols
An ether and an alcohol of the same molar mass have about the same solubility in water.
51
Some important chemical properties of ethers
1. Highly flammable 2. High vapor pressure 3. Reacts with O2 to form hydroperoxides and peroxides (unstable compounds which can explode)
52
Name
a hydroperoxide
53
Name
a peroxide
54
What are cyclic ethers?
The oxygen atom is part of a non-aromatic ring backbone
55
name
Ethylene oxide | -> an epoxide
56
The role of Lipid epoxides and peroxides?
Lipid epoxides and peroxides emerge upon exposition of plasma membranes to oxidative stress

Medical Chem (Organic chemistry) (7 decks)

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