1. Alcohols and
Phenols

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

7. Alcohol products
Product % of Ethyl Alcohol
BEER 3.5-9
WINE 12
BRANDY 40-45
WHISKEY 45-55
RUM 45

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

15. Experimental Result
most
reactive
more
reactive
least
reactive
Reactivity
turbidity
3o-butyl alcohol
turbidity
2o-butyl alcohol
turbidity
n-butyl alcohol
Product/s 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)
yl-2-propanol
OH
Cyclohexanol
OH
OH
OH
Ethanol
yl alcohol)
1-Propanol
(Propyl alcohol)
2-Propanol
(Isopropyl alcohol)
-Butanol
tyl 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
Ethanol
(Ethyl alcohol) (Pr
1-Butanol
(Butyl alcohol)
OH
OH
(sec-
2-Methyl-2-prop
(tert-Butyl alco
OH
Ethanol
(Ethyl alcohol)
1-Propanol
(Propyl alcohol) (Iso
1-Butanol
(Butyl alcohol)
OH
OH OH
2-Butanol
(sec-Butyl alcohol)
2-Me
(Iso
2-Methyl-2-propanol
(tert-Butyl alcohol)
O
Cyclohexan
(Cyclohexyl al
OH
OH
Ethanol
(Ethyl alcohol)
1-Propanol
(Propyl alcoh
1-Butanol
(Butyl alcohol)
OH
OH OH
2-Butanol
(sec-Butyl alco
2-Methyl-2-propanol
(tert-Butyl alcohol) (Cy
OH
OH
2-chloro-2-methylpropane
2-chlorobutane
I-chlorobutane

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

23. Results
Sample Color Indication
N-butyl Yellow Negative
Phenol Blue Positive

24.  Esterification
 Reactants: alcohol + carboxylic acid
 Product formed: ESTER
 Positive result: distinct fragrant odor
 General equation:
O O
ιι ιι
R-OH + R-C-OH  R-C-O-R + H2O
Alcohol Carboxylic acid Ester
CH3 C-OH
O
H-OCH2 CH3
H2 SO4
CH3 COCH2 CH3
O
H2 O
Ethanoicacid
(Aceticacid)
++
Ethyl ethanoate
(Ethyl acetate)
Ethanol
(Ethyl alcohol)

26. Experimental Result
Mint odor
Methanol
Paste
glue odor
Phenol
ProductOdorAcid ReactantCompound
Methyl salicylate

27. END!!!