Alcohols, Phenols, and

Ethers

Revised By :Dr. Marham Sitorus, M. Si

Chapter Objectives

 1.What is the general structure for an alcohol? A

phenol? An ether?
 2.What are functional groups? Why are they useful
in the study of organic chemistry?
 3.What structural feature is used to classify alcohols
as primary, secondary, or tertiary?
 4.How are alcohols named by the common and
IUPAC systems?
 5.Why are the boiling points of alcohols higher than
those of ethers and alkanes of similar molar
masses?
Objectives Con’t

 6.Why are alcohols and ethers of four carbons or

less soluble in water while comparable alkanes are
not?
 7.How are alcohols prepared from alkenes? What is
Markovnikov's rule?
 8.How do various alcohols affect the human body?
 9.What are the major reactions of alcohols?
 10.What product is formed by the oxidation of a
primary alcohol? A secondary alcohol? A tertiary
alcohol?
Objectives Con’t

 11.Describe the structure and uses of some

common polyhydric alcohols.
 12.Describe the structure and uses of some
phenols.
 13.How does the structural difference between
alcohols and ethers affect their physical
characteristics and reactivity?
 14.How are simple ethers named? Describe the
structure and uses of some ethers.
Sec. 14.1
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 Con’t

 Alcohols
 R-O-H
 Phenols
 Ar-OH
 Benzene ring with an OH
 Ethers
 R-O-R
Functional Groups

 Group of atoms which confers characteristic

properties on a family of organic compounds
 OH
 COOH
 Alkanes: none
Sec. 14.2 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
 RCH2OH
 Secondary Alcohol
 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 less—soluble in water
Sec. 14.4
Preparation of Alcohols
 Hydration Reactions
Markovnikov’s 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)

It’s the alcohol that’s found in those certain

beverages that people shouldn’t drink
Production of Alcohols Con’t

 Wines
 12% ethanol
 Champagnes
 14-20% ethanol
 Beers
 4% ethanol
 Whiskey
 50% ethanol

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

alcohol content by volume (whiskey: 100 proof)
Sec. 14.5
Physiological Effects of Alcohols
 LD50 (Lethal dose to 50% of a population)
 Tested on animals
 Varies per species though
 See table 14.5
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
Sec. 14.6
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
 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
Oxidation Con’t
Sec. 14.7 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 groups—extensive
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
Sec. 14.8
Phenols
 Slightly acidic
 Neutralized by strong bases
Phenols

 Used as:
 Antiseptic
 Disinfectants

First used was pure phenol—proved to be too toxic

 Methyl derivatives
 Cresols
 Creosote
Phenols

 Dihydroxybenzenes

 Components of biochemical molecules

Sec. 14.9
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 points—no hydrogen bonds
 Diethyl ether
 Forms a peroxide in air
 First general anesthetic