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Org Mol > Alcohols, Phenols, and Ethers > Flashcards

Alcohols, Phenols, and Ethers Flashcards

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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
Williamson ether synthesis is a chemical reaction that combines an __ and an __ __, with the help of a __
- alcohol - alkyl halide - base
26
product of Williamson ether synthesis
ether by replacing halogen atom with alkoxide group
27
source of phenols
Cumene hydroperoxide reaction
28
Cumene hydroxide reaction is the process of converting __ __ into __ and __
- cumene hydroperoxide - phenol - acetone
29
Cumene hydroperoxide reaction converts cumene hydroperoxide to phenol and acetone through a chemical decomposition known as __ __
Hock rearrangement
30
uses of alcohols
1. beverages 2. solvents 3. disinfectants and antiseptics 4. fuel
31
uses of ethers
1. solvents 2. fuel additives 3. laboratory reagents 4. industrial applications
32
uses of phenols
1. preservatives 2. fragrances and flavors 3. pharmaceuticals 4. dyes and pigments
33
reaction of alcohols
1. acids and bases 2. oxidation 3. dehydration
34
alcohols are __; they can act as both acid or base
amphoteric
35
alcohols are __ acids and __ bases
- mild (acids) - weak (bases)
36
better leaving group
conjugate acid
37
better nucleophile
conjugate base
38
every acid-base reaction has 4 components. what are these?
- acid - base - conjugate acid - conjugate base
39
the equilibrium will favor the direction where a __ acid and __ base produce a __ acid and __ base
stronger to weaker
40
measure acidity of alcohol using term called __
pKa
41
measure of equilibrium constant for a species giving up a proton to form its conjugate base
pKa
42
stronger acid + stronger base --> weaker acid + weaker base: form break
form N-H break O-H
43
favorable acid-base reaction of alcohols
stronger acid + stronger base --> weaker acid + weaker base
44
the __ the acid, the weaker the conjugate base
stronger
45
weaker acid + weaker base --> stronger acid + stronger base: form break
form O-H break N-H
46
the __ the acid, the stronger the conjugate base
weaker
47
a (very) unfavorable acid-base reaction of alcohols
weaker acid + weaker base --> stronger acid + stronger base
48
the lower pKa will be the __ acid
stronger
49
the higher pKa will be the __ acid
weaker
50
primary alcohols can be oxidized to form __ and __ __
- aldehydes - carboxylic acids
51
secondary alcohols can be oxidzed to give __
ketones
52
tertiary alcohols cannot be oxidized without breaking the __ bonds
C-C
53
carbon loses __ __ as it becomes more oxidized
electron density
54
when a carbon atom in an organic compounds loses a bond to __ and gains a new bond to __, it has been oxidized
- hydrogen (lose) - oxygen (gain)
55
Three-step mechanism of dehydration of alcohols to alkenes
1. formation of protonated alcohol 2. formation of carbocation 3. formation of alkenes
56
- the alcohol is acted upon by a protic acid - reversible step which takes place very quickly
formation of protonated alcohol
57
- C-O bond breaks - slowest step - considered as rate-determining step
carbocation formation
58
- protonation generated is eliminated with help of base - caron atom adjacent to carbocation breaks the existing C-H bond
alkene formation
59
acidic nature of phenols is dictated on its reaction with activie metals like __ and __ where __ is formed
- sodium - potassium - phenoxide
60
acidity has to do with the __ of the phenol
resonance
61
spreading of electrons in the molecule leading to an increased stability
resonance
62
stability further __ acidity of phenols
increases
63
phenols are highly prone to EAS due to __ __ __
rich electron density
64
Five stages of EAS in phenols
1. activation 2. attack of electrophiles 3. sigma formation 4. rearrange 5. final product
65
phenols start EAS when activated through the donation of electrons from lone pairs on oxygen atom to the ring
activation
66
electrophile approaches and attacks the now electron-rich ring
attack of electrophiles
67
electrophile replaces ane of hydrogen ions in aromatic ring resulting in formation of sigma complex
sigma formation
68
electrophile attaches to the ring and disrupts aromaticity temporarily
sigma complex
69
sigma complex is rearranged for aromaticity to be regained
rearrange
70
electrophile is bonded covalently and substituent phenol product is formed
final product
71
phenols that are treated with dilute nitric acid undergoes __ at low temperature to give mixture of ortho and para nitrophenols
nitration
72
occurs when hydroxyl group and nitro group is attached to the 1 and 2 position of the ring
ortho nitrophenol
73
occurs when hydroxyl and nitro group is attached at 1 and 4 positions of the ring
para nitrophenol
74
Types of halogenation of ethers
1. chlorination of ethers 2. bromination
75
common organic chemical reaction in which an ehter is hydrolyzed by an acid to form an alcohol and a protonated alcohol
cleavage of ethers by acids
76
cleavage of ethers by acids form __ and __ __
- alcohol - protonated alcohol
77
Two forms of nucleophilic substitution
1. SN1 2. SN2
78
nucleophilic substitution reaction: SN1 involves __ __
one molecule
79
nucleophilic substitution reaction: Sn2 involves __ __
two molecules

Org Mol (12 decks)

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