Alcohols, Phenols, and Ethers
ZAYANB ABD ELHAMED
Sec. 14.1
General Formulas and Functional Groups

Two of the three families contain a hydroxyl group
(OH)
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Alcohols
Phenols
Ethers

Often made from alcohols and phenols
All are considered organic derivatives of water.
General Formulas

Bent molecule
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Central oxygen atom
Hydrogen and alkyl group attached (R) alcohol or
an aryl group (Ar ) phenol
Classification of Alcohols

How many carbon attached to carbon with OH?
Classification of Alcohols
General Formulas

Alcohols
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
Phenols
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R-O-H
Ar-OH
Benzene ring with an OH
Ethers

R-O-R
NOMENCLUTURE OF ALCOHOLS
COMMON NAME:
ALKYL GROUP + WORD ALCOHOL
ETHYL ALCOHOL
CH3-CH2-OH
Isopropyl alcohol
CH3-CHOH-CH3
Nomenclature:
 Count the number of carbon atoms in the longest continuous
carbon chain containing the OH GROUP
 Change the ending from e by OH
 Indicate the position of OH GROUP by the lowest possible
number
CH3 OH
Methanol
CH3CH2CH2 OH
1- Propanol
Physical Properties of Alcohols


Replacement of hydrogen with a hydroxyl
group greatly changes properties
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
Production of Alcohols

Ethanol

Produced from sugars or starches by fermentation

C6H10O5  C6H12O6 2CH3CH2OH + 2CO2
It’s the alcohol that’s found in those certain beverages that people
shouldn’t drink


Toxic to humans
Acute poisoning kills several hundred a year (drinking
contests)
Isopropyl Alcohol




Rubbing alcohol
Rapid evaporation
Antiseptic
Used for the manufacture of acetone
Sec. 14.6
Chemical Properties of Alcohols

Reactions

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Occur on the functional groups
May involve hydrogen atoms as well
Dehydration
Oxidation
Dehydration


Removal of water
Sulfuric acid as a catalyst
Oxidation


Result depends on if alcohol is primary, secondary,
or tertiary
Primary
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
Secondary


Produces an aldehyde
Then goes through further oxidation to produce a
carboxylic acid
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
Dihydric alcohols
Trihydric alcohols
ethylene glycol



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
Sec. 14.8
Phenols

Neutralized by strong bases
Phenols
• Ingredients in cloves, vanillia, nutmeg, mint
Phenols

Dihydroxybenzenes
Sec. 14.9
Ethers

Derivatives of water
Both hydrogen atoms are replaced

Naming



Symmetrical
Name groups attached and add ether
Properties



Quite inert
Low boiling points—no hydrogen bonds
Diethyl ether


Forms a peroxide in air
First general anesthetic
Conversion of Alcohols into Esters
28