Alcohols and Phenols
ALCOHOLa compound that contains an -OH
(hydroxyl) group bonded to a tetrahedral carbon.
Methanol (CH3OH): simplest alcohol
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.
USES OF ALCOHOLS
Disinfectants Solvents Liquor High efficiency fuels Used to synthesize
other organic compounds
FungicidesCosmeticsUsed to make vinegarUsed in the manufacturing of plastics
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.
DANGEROUS PROPERTIES
Very combustible Poisonous to an extent Addiction Bodily damage caused by exposure
Alcohol products
Product % of Ethyl Alcohol
BEER 3.5-9
WINE 12
BRANDY 40-45
WHISKEY 45-55
RUM 45
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
Isopropyl Alcohol
Rubbing alcohol Rapid evaporation Antiseptic More toxic than ethanol, but induces
vomitting Used for the manufacture of acetone
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
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
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.
Experimental Result1 ml water + Solubility pHMethanol Miscible BasicEthanol Miscible Basic
Propanol Miscible BasicN-butyl Immiscible BasicN-amyl Immiscible BasicPhenol Immiscible Acidic
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 + H2OZnCl2 ,HCl
Experimental Result
most reactive
more reactive
least reactive
Reactivity
turbidity
3o-butyl alcohol
turbidity
2o-butyl alcohol
turbidity
n-butyl alcohol
Product/s formedVisible
(+) ResultCompound
Ethanol(Ethyl alcohol)
1-Propanol(Propyl alcohol)
2-Propanol(Isopropyl alcohol)
1-Butanol(Butyl alcohol)
OH
OH
OHOH
2-Butanol(sec-Butyl alcohol)
2-Methyl-1-propanol(Isobutyl alcohol)
2-Methyl-2-propanol(tert-Butyl alcohol)
OH
Cyclohexanol(Cyclohexyl alcohol)
OHOH
OH
Ethanol(Ethyl alcohol)
1-Propanol(Propyl alcohol)
2-Propanol(Isopropyl alcohol)
1-Butanol(Butyl alcohol)
OH
OH
OHOH
2-Butanol(sec-Butyl alcohol)
2-Methyl-1-propanol(Isobutyl alcohol)
2-Methyl-2-propanol(tert-Butyl alcohol)
OH
Cyclohexanol(Cyclohexyl alcohol)
OHOH
OH
Ethanol(Ethyl alcohol)
1-Propanol(Propyl alcohol)
2-Propanol(Isopropyl alcohol)
1-Butanol(Butyl alcohol)
OH
OH
OHOH
2-Butanol(sec-Butyl alcohol)
2-Methyl-1-propanol(Isobutyl alcohol)
2-Methyl-2-propanol(tert-Butyl alcohol)
OH
Cyclohexanol(Cyclohexyl alcohol)
OHOH
OH
Ethanol(Ethyl alcohol)
1-Propanol(Propyl alcohol)
2-Propanol(Isopropyl alcohol)
1-Butanol(Butyl alcohol)
OH
OH
OHOH
2-Butanol(sec-Butyl alcohol)
2-Methyl-1-propanol(Isobutyl alcohol)
2-Methyl-2-propanol(tert-Butyl alcohol)
OH
Cyclohexanol(Cyclohexyl alcohol)
OHOH
OH
Ethanol(Ethyl alcohol)
1-Propanol(Propyl alcohol)
2-Propanol(Isopropyl alcohol)
1-Butanol(Butyl alcohol)
OH
OH
OHOH
2-Butanol(sec-Butyl alcohol)
2-Methyl-1-propanol(Isobutyl alcohol)
2-Methyl-2-propanol(tert-Butyl alcohol)
OH
Cyclohexanol(Cyclohexyl alcohol)
OHOH
OH
Ethanol(Ethyl alcohol)
1-Propanol(Propyl alcohol)
2-Propanol(Isopropyl alcohol)
1-Butanol(Butyl alcohol)
OH
OH
OHOH
2-Butanol(sec-Butyl alcohol)
2-Methyl-1-propanol(Isobutyl alcohol)
2-Methyl-2-propanol(tert-Butyl alcohol)
OH
Cyclohexanol(Cyclohexyl alcohol)
OHOH
OH
2-chloro-2-methylpropane
2-chlorobutane
I-chlorobutane
Lucas Test
Alcohols: 2 layers formed, 2nd layer turbidity
Phenol: 1st layer turbidity
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
Oxidation
Oxidation by KMnO4
(dehydrogenation) Oxidizing agent:
KMnO4
Positive result: Decolorization with brown precipitation
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
R - C - H + KMnO4
OH
H
heatR - C - OH + MnO2 + KOH
O
R - C - R' R - C - R'
OH O
H
[O] R - C - R'
OH
[O]
R''
NO REACTION
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 FormedVisible (+)
ResultCompound
Ethanol(Ethyl alcohol)
1-Propanol(Propyl alcohol)
2-Propanol(Isopropyl alcohol)
1-Butanol(Butyl alcohol)
OH
OH
OHOH
2-Butanol(sec-Butyl alcohol)
2-Methyl-1-propanol(Isobutyl alcohol)
2-Methyl-2-propanol(tert-Butyl alcohol)
OH
Cyclohexanol(Cyclohexyl alcohol)
OHOH
OH
Ethanol(Ethyl alcohol)
1-Propanol(Propyl alcohol)
2-Propanol(Isopropyl alcohol)
1-Butanol(Butyl alcohol)
OH
OH
OHOH
2-Butanol(sec-Butyl alcohol)
2-Methyl-1-propanol(Isobutyl alcohol)
2-Methyl-2-propanol(tert-Butyl alcohol)
OH
Cyclohexanol(Cyclohexyl alcohol)
OHOH
OH
Ethanol(Ethyl alcohol)
1-Propanol(Propyl alcohol)
2-Propanol(Isopropyl alcohol)
1-Butanol(Butyl alcohol)
OH
OH
OHOH
2-Butanol(sec-Butyl alcohol)
2-Methyl-1-propanol(Isobutyl alcohol)
2-Methyl-2-propanol(tert-Butyl alcohol)
OH
Cyclohexanol(Cyclohexyl alcohol)
OHOH
OH
3-Methylbutanal 2-Propenal(Acrolein)
Hexanal
12
34H
O
H
O1
23
45
6
123
H
O
butanalO
CH3CH
O
CH3COH
Acetaldehyde Acetic acid Ethyl isopropyl ketoneMethyl ethyl ketone
OO
butanone
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
Results
Sample Color Indication N-butyl Yellow Negative Phenol Blue Positive
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
CH3C-OHO
H-OCH2CH3H2SO4
CH3COCH2CH3
OH2O
Ethanoic acid(Acetic acid)
++
Ethyl ethanoate(Ethyl acetate)
Ethanol(Ethyl alcohol)
Experimental Result
Mint odor
Methanol
Paste glue odor
Phenol
ProductOdorAcid ReactantCompound
Methyl salicylate
END!!!