2. ALCOHOL
a compound that contains an -OH
(hydroxyl) group bonded to a
tetrahedral carbon.
Methanol (CH3OH): simplest alcohol
3. CHEMICAL PROPERTIES
An alcohol is made up of a chain of carbons
and hydrogen, where an –OH molecule
attaches to where a Hydrogen molecule is
supposed to be attached to a Carbon.
The position of the OH group has little effect
on the chemical properties except in their
response to mild oxidizing agents.
4. USES OF ALCOHOLS
Disinfectants
Solvents
Liquor
High efficiency fuels
Used to synthesize
other organic
compounds
Fungicides
Cosmetics
Used to make
vinegar
Used in the
manufacturing of
plastics
5. USES (CONTINUED)
Methanol- Solvent for fats, oils, and resins.
Manufacture of dyes, antifreeze, and
plastics.
Ethanol- Solvent for paints, glues,
pharmaceuticals, and explosives.
Cyclohexanol-Intermediate in making
chemicals used in nylon manufacture.
6. DANGEROUS PROPERTIES
Very combustible
Poisonous to an extent
Addiction
Bodily damage caused by exposure
8. Ethanol
Toxic to humans
Acute poisoning kills several hundred a
year (drinking contests)
Long term poisioning
Most serious drug problem in US
40 times more addicts than heroin
9. Isopropyl Alcohol
Rubbing alcohol
Rapid evaporation
Antiseptic
More toxic than ethanol, but induces
vomitting
Used for the manufacture of acetone
10. PHYSICAL PROPERTIES
Boiling point increases as MW increases.
Solubility in water decreases as MW (due to
increase in C-H) increases.
Alcohols are semi-polar molecules
C-O and O-H bonds: polar covalent
C-H bonds: non-polar covalent
11. Phenol
The antiseptic property of phenol was discovered
in 1865 by Joseph Lister, a physician in Scotland.
Listerine, named after him, contains phenol as the
active ingredient.
Today, over two million tons of phenol are made
each year in the US alone.
Phenol is used for resins, glue to make plywood,
plastics, and pharmaceuticals.
OH
12. Phenols Ar-OH
Phenols are compounds with an –OH
group attached to an aromatic carbon.
Although they share the same functional
group with alcohols, where the –OH
group is attached to an aliphatic carbon,
the chemistry of phenols is very different
from that of alcohols.
13. Experimental Result
1 ml water + Solubility pH
Methanol Miscible Basic
Ethanol Miscible Basic
Propanol Miscible Basic
N-butyl Immiscible Basic
N-amyl Immiscible Basic
Phenol Immiscible Acidic
14. CHEMICAL PROPERTIES
Reaction with Lucas Reagent
Lucas reagent: ZnCl2 in HCl
Positive result: formation of turbidity or
two layers
General equation:
R - OH R - Cl + H2O
ZnCl2,HCl
16. Lucas Test
Alcohols: 2 layers formed, 2nd layer
turbidity
Phenol: 1st layer turbidity
17. Lucas Test
Used to classify low
molecular weight
alcohols
no visible reaction at room
temperature and cloudy
only on heating: primary
solution turns cloudy in 3–5
minutes: secondary
solution turns cloudy
immediately, and/or phases
separate: tertiary
18. Oxidation
Oxidation by KMnO4
(dehydrogenation)
Oxidizing agent:
KMnO4
Positive result:
Decolorization
with brown
precipitation
19. Oxidation
Primary
Produces an aldehyde
Then goes through further oxidation to produce a
carboxylic acid
Secondary
Produces a ketone
Tertiary
No reaction
Can’t break the carbon-carbon bond
Phenol
Produces quinones
20. R - C - H + KM4
OH
H
heat
R - C - OH2 +
O
R - C - R' R - C - R'
OH O
H
[O]
R - C - R'
OH
[O]
R''
NO REAC
21. Experimental Result
compound
was not
oxidized
compound
was oxidized
compound
was oxidized
Interpretation
none
Negative
result
3o-butyl alcohol
decolorization
with brown
precipitation
2o-butyl alcohol
decolorization
with brown
precipitation
n-butyl alcohol
Product Formed
Visible (+)
Result
Compound
Ethanol
(Ethyl alcohol)
1-Propanol
(Propyl alcohol)
2-Propanol
(Isopropyl alcohol)
1-Butanol
(Butyl alcohol)
OH
OH
OH
OH
2-Butanol
(sec-Butyl alcohol)
2-Methyl-1-propanol
(Isobutyl alcohol)
2-Methyl-2-propanol
(tert-Butyl alcohol)
OH
Cyclohexanol
(Cyclohexyl alcohol)
OH
OH
OH
1-Propanol
(Propyl alcohol)
2-Propanol
(Isopropyl alcohol)
OH
OH
2-Butanol
(sec-Butyl alcohol)
2-Methyl-1-propanol
(Isobutyl alcohol)
-propanol
l alcohol)
OH
Cyclohexanol
(Cyclohexyl alcohol)
OH
OH
OH
anol
alcohol)
1-Propanol
(Propyl alcohol)
2-Propanol
(Isopropyl alcohol)
tanol
alcohol)
OH
OH
OH
OH
2-Butanol
(sec-Butyl alcohol)
2-Methyl-1-propanol
(Isobutyl alcohol)
2-Methyl-2-propanol
(tert-Butyl alcohol)
OH
Cyclohexanol
(Cyclohexyl alcohol)
OH
OH
OH
3-MHexanal
4
H
O
1
2
3
4
5
6
butanal
O
CH3CH
O
CH3COH
Acetaldehyde Acetic acid Methyl ethyl ketone
O
butanone
22. Iron chloride test
Used to detect
phenols
The formation of a
red, blue, green, or
purple coloration
indicates the
presence of phenols
The ferric chloride
test can be used to
detect metabolites in
urine in case of
congenital metabolic
problems or genetic
diseases
