Chapter 5 Alcohols, Phenols, Ethers, and their Sulfur Analogues

1
Chapter 5Alcohols, Phenols, Ethers, and their
Sulfur Analogues
2
(No Transcript)
3
5.1 Structural Relations

• Alcohol Phenol Ether

4
5.1 Structural Relations
5
Constitutional Isomerism

• Build 2-propanol, 1-propanol, t-butyl alcohol
  (2-methyl-2-hydroxypropane), 2-butanol
• Results from
• 1)
• 2)

Different carbon skeletons
Different OH group placement
6
5.3 Classifying Naming Alcohols

• 1º Alcohol 2º Alcohol 3º Alcohol

7
5.3 Classifying Naming Alcohols
8
Naming Alcohols

• ltltsee separate Naming handoutgtgt
• ending e ? -ol
• number nearest OH group
• polyfunctional alcohols (gt 1 OH) are called
  diols, triols

9
Naming Alcohols-Answers

• 1-propanol
• 2-chloro-2-fluoro-5,5-dimethyl-3-heptanol
• 1,2,3-propanetriol or glycerol glycerin
• 2,4-hexanediol
• 2-propen-1-ol
• tert-butyl alcohol or 2- methyl-2-propanol

10
Naming Ethers

• methylethylether
• dipropyl ether
• ethyl2-methylbutylether
• isopropylphenylether
• dibenzylether

11
Box 5.1 Alcohols

• Methanol
• Ethanol

Manufacture of formaldehyde
sterno
Industrially, medically, production of plastics,
drugs and other chemicals Solvent, perfumes,
varnishes, antiseptics
12
Box 5.1 Alcohols

• Propanol
• Ethylene glycol (1,2-ethandiol)
• Propylene glycol (1,2-propanetriol)

Rubbing alcohol
solvent
Manufacture of acetone
Antifreeze (diol and water)
13
Box 5.1 Alcohols

• 1,2,3-propanetriol
• Menthol

glycerin or glycerol
Product in digestion of fats/oils
Only non-toxic alcohol
Increases secretions from mucous membranes ?
cough drops
14
Box 5.1 Alcohols

• Menthol

(peppermint oil) cough drops cigarettes Toothpaste
Shaving cream
15
(No Transcript)
16
(No Transcript)
17
Box 5.2 Types Alcoholic Beverages

• Ethanol can be produced by
• 1)
• 2)

Hydration of ethylene
Fermentation of grains, fruits, veggies
18
(No Transcript)
19
Box 5.2 Consumable Alcohol

• Starch ? ?

Ethanol CO2
glucose/fructose
Most alcohols gt 99 ethanol (tasteless) Rest
congeners
20
Box 5.2 Consumable Alcohol
Wines 10-14 Beer 3-8 Liquors gt50
light beer vs. dark beer
Low T High Temp (grain dried)
21
Box 5.3 Health Aspects Alcohol Consumption
Deleterious effects of drinking alcohol come
from your liver attempting to detoxify your body
of ethanol
Ethanol ? acetaldehyde
22
Box 5.3 Health Aspects Alcohol Consumption
Other alcohols are more toxic.
methanol ? ????
23
5.4 Physical Properties of Alcohols
KEY Alcohols have ___________
forces Properties 1) 2)
_______ m.p./b.p. than corresponding HCs
Soluble in ___________
24
Hydrogen bonding
25
(No Transcript)
26
5.7 The Oxidation of Alcohols
Oxidation can occur by 1) 2)
Combustion (? CO2)
Selective oxidation
Ox. Occurs at ____________
Reagents used ________________
27
5.7 The Oxidation of Alcohols
Primary ? ___________ ?___________ alcohol
28
(No Transcript)
29
5.7 The Oxidation of Alcohols
Secondary ? ___________ alcohol
30
(No Transcript)
31
5.7 The Oxidation of Alcohols
tertiary ? ___________ alcohol
32
(No Transcript)
33
MnO4- and Cr2O72- Diagnostic Tests
Alcohols 1 2 3
Alkanes, cyclos, aromatics, ethers
(pos)
- (neg)
(pos)
Alkenes,kynes,phenols
(pos)
- (neg)
Cr2O72- is used for BALs
34
5.8 Phenols - OMIT
35
(No Transcript)
36
5.9 Ethers

• Structure
• ltltsee separate Naming handoutgtgt
• Well name simple ones only
• Name each group separately (in alpha order)

37
(No Transcript)
38
(No Transcript)
39
5.9 Ethers

• Properties
• Ethers have ______________ forces.
• 1) m.p./b.p.
• 2) solubility

dipole-dipole
alkanes lt ethers lt alcohols
alkanes lt ethers lt alcohols
Note This effect ______ as chain lengthens.
40
5.9 Ethers

• Hydrogen bonding with water

41
5.9 Ethers (Reactivity)

• Unreactive towards
• Reactions
• 1)
• 2)

acids/bases/ox. agent
combustion
Halogenation (omit)
42
5.9 Ethers - Uses

• Uses
• Halogenated ethers are ______________ than ethers.

anesthetic
solvent
less volatile/flammable
(also have milder side effects)
43
5.6 5.10 Dehydration of Alcohols

• CH3CH2CH2-OH

CH3CHCH2
H2SO4
Major _at_ 180º C
H2SO4
CH3CH2CH2-O-CH2CH2CH3
Major _at_ 140º C
44
(No Transcript)
45
5.6 5.10 Dehydration of Alcohols

• CH3CH2-OH

CH2CH2
H2SO4
Major _at_ 180º C
H2SO4
CH3CH2-O-CH2CH3
Major _at_ 140º C
46
5.11 Thiols Sulfur Analogues of alcohols

• Alcohol Thiol
• -SH group mercapto or sulfhydryl group
• Omit Naming, properties etc.

47
(No Transcript)
48
(No Transcript)
49
5.11 Thiols Sulfur Analogues of alcohols

• Disulfides
• 2 R-S-H ?
• 2 R-SH M2 ?

CH2CH2
50
(No Transcript)