Alcohols and Phenols

General Formulas and

Functional
Groups
Two of the three families contain a hydroxyl group
(OH)

Alcohols
Phenols

Ethers

Often made from alcohols and phenols

All are considered organic derivatives of water.

General Formulas

Bent molecule

Central oxygen atom

Hydrogen and alkyl group attached (R) or an aryl
group (Ar)

General Formulas Cont

Alcohols

Phenols

R-O-H
Ar-OH
Benzene ring with an OH

Ethers

R-O-R

Classification and Nomenclature

of Alcohols

Properties of alcohols depend on the

arrangement of the carbon atoms of the
molecule
Primary (1) carbon atom

Secondary (2) carbon atom

Tertiary (3) carbon atom

Classification and Nomenclature

of Alcohols

Primary Alcohol

Secondary Alcohol

RCH2OH
R2CHOH

Tertiary Alcohol

R3COH

IUPAC Naming

Name the longest continous chain of carbons

containing the OH group
Number which carbon the OH is attached to
End name in ol
If more than one hydroxyl group, use suffixes
diol, -triol, etc.

Physical Properties of
Alcohols

Replacement of hydrogen with a hydroxyl

group greatly changes properties
Not as homologous as alkanes
Higher boiling points

Due to strong intermolecular attractions

Solubility

The more compact the molecule is, the more

soluble it is
4-5 carbons or lesssoluble in water

Preparation of Alcohols

Hydration Reactions

Markovnikovs Rule

The hydroxyl group goes on the carbon with

fewer hydrogens

Production of alcohols

Methanol

1.7 billion gallons produced a year

Used in formaldehyde, acetic acid, fuels
(MTBE), silicones, refrigerants

Production of Alcohols

Ethanol

Produced from sugars or starches by fermentation

C6H10O5 C6H12O6 2CH3CH2OH + 2CO2

(Enzymes as catalysts)
Its the alcohol thats found in those certain
beverages that people shouldnt drink

Production of Alcohols Cont

Wines

Champagnes

14-20% ethanol

Beers

12% ethanol

4% ethanol

Whiskey

50% ethanol

Proof spirit: alcoholic content of a beverage, twice that of the

alcohol content by volume (whiskey: 100 proof)

Physiological Effects of Alcohols

LD50 (Lethal dose to 50% of a population)

Tested on animals
Varies per species though

Methanol

Can cause permanent blindness or death in

high amounts
Vapors are very dangerous as well

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

Chemical Properties of Alcohols

Reactions

Occur on the functional groups

May involve hydrogen atoms as well
Dehydration
Oxidation

Dehydration

Removal of water
Sulfuric acid as a catalyst
Produces:

Ether (excess ROH) + water

Alkene (excess H2SO4) + water

Oxidation

Result depends on if alcohol is primary, secondary,

or tertiary
Primary

Secondary

Produces an aldehyde
Then goes through further oxidation to produce a
carboxylic acid
Produces a ketone

Tertiary

No reaction
Cant break the carbon-carbon bond

Oxidation Cont

Multifunctional Alcohols:
Glycols and Glycerol

More than one hydroxyl group

Polyhydric groups
Dihydric alcohols
Trihydric alcohols

Glycols

Dihydric alcohols
1,2 ethanediol (ethylene glycol)
HOCH2CH2OH

Two hydroxyl groupsextensive

intermolecular hydrogen bonding

Higher boiling point

Used as anti-freeze

Glycerol

Most important trihydric alcohol

Syrupy liquid
Nontoxic, product of the hydrolysis of fats and
oils
Nitroglycerin

Detonates on slight impact

Reaction produces temps of 3000 C and
pressures above 2000 atm

Phenols

Slightly acidic
Neutralized by strong bases

Phenols

Used as:

Antiseptic
Disinfectants

First used was pure phenolproved to be too toxic

Methyl derivatives

Cresols

Creosote

Phenols

Dihydroxybenzenes

Components of biochemical molecules

Ethers

Derivatives of water
Both hydrogen atoms are replaced

Naming

Symmetrical
Name groups attached and add ether

Properties

Quite inert
Although react violently in the air
Low boiling pointsno hydrogen bonds
Diethyl ether

Forms a peroxide in air

First general anesthetic