Ethers: Dr. Naureen Shehzadi

ETHERS
DR. NAUREEN SHEHZADI

DEFINITION
• Ether comes from the Latin aether, means “to ignite”.

• Ethers have high vapor pressure at room temperature, which makes them
very flammable.
All ethers are compounds in which two organic groups are connected to
a single oxygen atom.
FORMULA
- The general formula for an ether is R-O-R’, where R and R’ may be identical or
different, and they may be alkyl or aryl groups
TYPES
Ethers
Symmetrical Unsymmetrical
When the organic

When the organic
groups attached to
groups attached to the
the oxygen are
oxygen are different.
identical.
NOMENCLATURE
Common names:
Ethers are usually named by giving

the name of each alkyl or aryl
group, in alphabetical order,
followed by the word ether.
IUPAC system:
For ethers with more complex structures, it may be necessary to name the
-OR group as an alkoxy group. In the IUPAC system, the smaller alkoxy
group is named as a substituent.
PHYSICAL PROPERTIES
Physical state
Ethers are colorless compounds with characteristic, relatively pleasant odors.
Boiling point
They have lower boiling points than alcohols with an equal number of carbon
atoms. In fact, an ether has nearly the same boiling point as the corresponding
hydrocarbon in which a -CH2- group replaces the ether’s oxygen. Because of
their structures (no O-H bonds), ether molecules cannot form hydrogen
bonds with one another.
Water solubility
Low-molecular-weight ethers, such as dimethyl ether, are quite soluble in
water. Ether molecules can form hydrogen bonds to water.
PREPARATION
There are two general methods for synthesizing ethers.
Dehydration of alcohols
It is used commercially and in the laboratory to make certain symmetrical
ethers.
Williamson synthesis
General laboratory method used to prepare all kinds of ethers, symmetrical
and unsymmetrical.
1- DEHYDRATION OF ALCOHOLS
It takes place in the presence of acid catalysts (H2SO4, H3PO4)

(intermolecular reaction).
Example:
The most important commercial ether is diethyl ether. It is prepared from
ethanol and sulfuric acid.
2- WILLIAMSON SYNTHESIS
An alcohol is converted to its alkoxide by treatment with a reactive metal

(sodium or potassium). Displacement is carried out between the alkoxide and
an alkyl halide (primary rather than a secondary or tertiary)
CHEMICAL PROPERTIES
Ethers are quite stable compounds.
The ether linkage does not react with bases, reducing agents, oxidizing agents,
or active metals.
Ethers react only under strongly acidic conditions.
Cleavage of Ethers by Hot Concentrated Acids

When ethers are heated in concentrated acid solutions, the ether linkage is
broken. The acids most often used in this reaction are HI, HBr, and HCl.
If an excess of acid is present, the alcohol initially produced is converted into
an alkyl halide by the reaction.
CYCLIC ETHERS
Cyclic ethers whose rings are larger than the three-membered epoxides are
known. The most common are five- or six-membered rings.
Epoxides are cyclic ethers in which the ether oxygen is part of a three
membered ring.
PREPARATION
• The most important commercial epoxide is ethylene oxide, produced by

the silver-catalyzed air oxidation of ethene.
• Other epoxides are usually prepared by the reaction of an alkene with an
organic peracid.
REACTIONS
Reaction with water

They undergo acid-catalyzed ring opening to give glycols.
Reaction with alcohols and hydrohalic acid
Reaction with Grignard's reagent
They undergo acid-catalyzed ring opening to give alcohols.
Reaction with amines
They undergo acid-catalyzed ring opening to give hydroxy amines.
IMPORTANCE
1. Solvent (non-polar)
2. Partitioning of herbal extracts
3. Preparation of herbal extraction
4. Diethyl ether was the first general anesthetic used in surgeries (now its
use in clinical setting is prohibited, only used to induce anesthesia in
laboratory animals)
ETHEREAL GENERAL ANESTHETICS
CROWN ETHERS
A number of crown ethers have anti-microbial properties

ETHER VOLATILE OIL
Anethol is a phenolic ether obtained from fennel (Saunf) and is used in

aromatherapy

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ETHERS

DR. NAUREEN SHEHZADI

• Ether comes from the Latin aether, means “to ignite”.

When the organic

Ethers are usually named by giving

There are two general methods for synthesizing ethers.

It takes place in the presence of acid catalysts (H2SO4, H3PO4)

An alcohol is converted to its alkoxide by treatment with a reactive metal

Ethers are quite stable compounds.

Ethers react only under strongly acidic conditions.

Cleavage of Ethers by Hot Concentrated Acids

• The most important commercial epoxide is ethylene oxide, produced by

Reaction with water

A number of crown ethers have anti-microbial properties

Anethol is a phenolic ether obtained from fennel (Saunf) and is used in

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