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Org Mol > Alcohols, Phenols, and Ethers > Flashcards

Alcohols, Phenols, and Ethers Flashcards

1
Q
  • one of the most prevalent chemical molecules
  • widely produced organic chemicals
  • utilized as sweeteners and in creation of perfumes
A

alcohol

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2
Q

any one of a group of organic compounds that has a saturated carbon atom bonded to at least one OH functional group

A

alcohol

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3
Q

general formula of alcohol

A

R-OH

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4
Q

suffix molecule of alcohol

A

ol

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5
Q

Naming alcohol

A
  1. count longest chain
  2. look where OH is
    3 name it
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6
Q

organic compound that contains an OH group attached to a carbon atom in a benzene ring

A

phenol

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7
Q

common naming of phenols

A
  • ortho
  • meta
  • para
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8
Q

Naming phenol

A
  1. identify parent compound and substituent
  2. locate and number places of parent compound and substituent
  3. name
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9
Q

phenols are always the parent compound, except if there is an exemption rule, such as the prescence of __ __

A

benzoic acid

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10
Q

Naming phenols with benzoic acid

A
  1. make benzoic acid parent compound and phenol substituent
  2. label locations
  3. name
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11
Q

group of chemical substances that contain oxygen placed between two alkyl groups

A

ethers

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12
Q

ethers ___ designated suffix

A

do not have

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13
Q

Naming ethers

A
  1. alkoxy group with shorter chain is the substituent
  2. longest chain is parent chain
  3. substituents are placed alphabetically
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14
Q

alcohols have __ boiling points than molecules of the same molecular mass because of the hydroxyl group

A

higher

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15
Q

longer-chain alcohols have higher boiling points due to increased surface area, which enables stronger __ __ interactions

A

London dispersion

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16
Q

why do alcohols have higher boiling points

A

due to hydroxyl group which allows hydrogen bonding

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17
Q

why are alcohols soluble in water

A

due to ability to form hydrogen bonds with more water molecules

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18
Q

longer-chain alcohols is less soluble than smaller alcohol molecules due to __ __

A

steric hindrance

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19
Q

why do ethers have lower boiling points than alcohol

A

due to absence of H atom attached to O atom which makes hydrogen bonding difficult

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20
Q

solubility of ethers in water

A

sparingly soluble due to absence of H attached to O atom

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21
Q

ethers dissolve in organic solvents such as __ and __

A
  • benzene
  • chloroform
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22
Q

boiling point and solubility of phenol

A

have higher boiling point compared to similar molecules and are slightly soluble due to presence of -OH which enables hydrogen bonding

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23
Q

alcohols are produced through the __ and/or __ process of organic materials

A
  • fermentation
  • distillation
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24
Q

source of ethers

A

williamson ether synthesis

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25
Q

Williamson ether synthesis is a chemical reaction that combines an __ and an __ __, with the help of a __

A
  • alcohol
  • alkyl halide
  • base
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26
Q

product of Williamson ether synthesis

A

ether by replacing halogen atom with alkoxide group

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27
Q

source of phenols

A

Cumene hydroperoxide reaction

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28
Q

Cumene hydroxide reaction is the process of converting __ __ into __ and __

A
  • cumene hydroperoxide
  • phenol
  • acetone
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29
Q

Cumene hydroperoxide reaction converts cumene hydroperoxide to phenol and acetone through a chemical decomposition known as __ __

A

Hock rearrangement

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30
Q

uses of alcohols

A
  1. beverages
  2. solvents
  3. disinfectants and antiseptics
  4. fuel
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31
Q

uses of ethers

A
  1. solvents
  2. fuel additives
  3. laboratory reagents
  4. industrial applications
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32
Q

uses of phenols

A
  1. preservatives
  2. fragrances and flavors
  3. pharmaceuticals
  4. dyes and pigments
33
Q

reaction of alcohols

A
  1. acids and bases
  2. oxidation
  3. dehydration
34
Q

alcohols are __; they can act as both acid or base

A

amphoteric

35
Q

alcohols are __ acids and __ bases

A
  • mild (acids)
  • weak (bases)
36
Q

better leaving group

A

conjugate acid

37
Q

better nucleophile

A

conjugate base

38
Q

every acid-base reaction has 4 components. what are these?

A
  • acid
  • base
  • conjugate acid
  • conjugate base
39
Q

the equilibrium will favor the direction where a __ acid and __ base produce a __ acid and __ base

A

stronger to weaker

40
Q

measure acidity of alcohol using term called __

A

pKa

41
Q

measure of equilibrium constant for a species giving up a proton to form its conjugate base

A

pKa

42
Q

stronger acid + stronger base –> weaker acid + weaker base:
form break

A

form N-H
break O-H

43
Q

favorable acid-base reaction of alcohols

A

stronger acid + stronger base –> weaker acid + weaker base

44
Q

the __ the acid, the weaker the conjugate base

A

stronger

45
Q

weaker acid + weaker base –> stronger acid + stronger base:
form break

A

form O-H
break N-H

46
Q

the __ the acid, the stronger the conjugate base

A

weaker

47
Q

a (very) unfavorable acid-base reaction of alcohols

A

weaker acid + weaker base –> stronger acid + stronger base

48
Q

the lower pKa will be the __ acid

A

stronger

49
Q

the higher pKa will be the __ acid

A

weaker

50
Q

primary alcohols can be oxidized to form __ and __ __

A
  • aldehydes
  • carboxylic acids
51
Q

secondary alcohols can be oxidzed to give __

A

ketones

52
Q

tertiary alcohols cannot be oxidized without breaking the __ bonds

A

C-C

53
Q

carbon loses __ __ as it becomes more oxidized

A

electron density

54
Q

when a carbon atom in an organic compounds loses a bond to __ and gains a new bond to __, it has been oxidized

A
  • hydrogen (lose)
  • oxygen (gain)
55
Q

Three-step mechanism of dehydration of alcohols to alkenes

A
  1. formation of protonated alcohol
  2. formation of carbocation
  3. formation of alkenes
56
Q
  • the alcohol is acted upon by a protic acid
  • reversible step which takes place very quickly
A

formation of protonated alcohol

57
Q
  • C-O bond breaks
  • slowest step
  • considered as rate-determining step
A

carbocation formation

58
Q
  • protonation generated is eliminated with help of base
  • caron atom adjacent to carbocation breaks the existing C-H bond
A

alkene formation

59
Q

acidic nature of phenols is dictated on its reaction with activie metals like __ and __ where __ is formed

A
  • sodium
  • potassium
  • phenoxide
60
Q

acidity has to do with the __ of the phenol

A

resonance

61
Q

spreading of electrons in the molecule leading to an increased stability

A

resonance

62
Q

stability further __ acidity of phenols

A

increases

63
Q

phenols are highly prone to EAS due to __ __ __

A

rich electron density

64
Q

Five stages of EAS in phenols

A
  1. activation
  2. attack of electrophiles
  3. sigma formation
  4. rearrange
  5. final product
65
Q

phenols start EAS when activated through the donation of electrons from lone pairs on oxygen atom to the ring

A

activation

66
Q

electrophile approaches and attacks the now electron-rich ring

A

attack of electrophiles

67
Q

electrophile replaces ane of hydrogen ions in aromatic ring resulting in formation of sigma complex

A

sigma formation

68
Q

electrophile attaches to the ring and disrupts aromaticity temporarily

A

sigma complex

69
Q

sigma complex is rearranged for aromaticity to be regained

A

rearrange

70
Q

electrophile is bonded covalently and substituent phenol product is formed

A

final product

71
Q

phenols that are treated with dilute nitric acid undergoes __ at low temperature to give mixture of ortho and para nitrophenols

A

nitration

72
Q

occurs when hydroxyl group and nitro group is attached to the 1 and 2 position of the ring

A

ortho nitrophenol

73
Q

occurs when hydroxyl and nitro group is attached at 1 and 4 positions of the ring

A

para nitrophenol

74
Q

Types of halogenation of ethers

A
  1. chlorination of ethers
  2. bromination
75
Q

common organic chemical reaction in which an ehter is hydrolyzed by an acid to form an alcohol and a protonated alcohol

A

cleavage of ethers by acids

76
Q

cleavage of ethers by acids form __ and __ __

A
  • alcohol
  • protonated alcohol
77
Q

Two forms of nucleophilic substitution

A
  1. SN1
  2. SN2
78
Q

nucleophilic substitution reaction:
SN1 involves __ __

A

one molecule

79
Q

nucleophilic substitution reaction:
Sn2 involves __ __

A

two molecules

Org Mol (12 decks)

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