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Ethers

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34 views27 pages

Ethers

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safiabarkat5
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© © All Rights Reserved
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ETHERS

Dr. Zainab Waheed


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
When the organic
organic groups
groups attached
attached to the
to 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 (i.e alkane) in
which a -CH2- group replaces the ether’s oxygen. Because of
their structures (no O-H bonds), ether molecules cannot form
hydrogen
Water bonds with one another.
solubility
Low-molecular-weight ethers, such as dimethyl ether, are quite
soluble in water, as 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). Heating alcohol in acidic medium results in
condensation of two molecules of alcohol with the elimination of water
molecule to form ether.

Example: The most important commercial ether is diethyl ether. It is prepared


from ethanol and sulfuric acid.
Starting alcohol must be primary
Temperature should be kept at 140C
2- Williamson synthesis
This involves the treatment of sodium alkoxide with an alkyl halide. An alcohol
is converted to its alkoxide by treatment with a reactive metal (sodium or
potassium) ROH+Na→RONa+H2. Displacement is carried out between the
alkoxide and an alkyl halide. Both symmetrical and unsymmetrical ethers can
be made by this method.
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.
Reaction at ethereal oxygen
Formation of oxonium salts
Ether react with cold concentrated H2SO4 or HCl to give oxonium salts.
Ethers donate a pair of electrons to a Hydrogen ion to form salts.
Oxonium salts are soluble in acid solution. Ethers can be regenerated
from oxonium salts on treatment with water. This reaction can be used
to distinguish between ethers and alkanes. As alkanes don’t react with
conc. acids.

Reaction involving C-O bonds


Reaction with PCl5
Reaction of sulfuric acid
Ethers react with hot H2SO4 to form alcohol and alkyl hydrogen.

Action of acid derivatives


Ethers reacts with acid chlorides and acid anhydrides in the presence of
catalyst such as anhydrous AlCl3 or ZnCl2 to form esters and haloalkanes
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 at 200- 400C under pressure.
Other epoxides are usually prepared by the reaction of an
alkene with an organic peracid (peracetic acid).

Industrially, ethylene oxide is prepared by the reaction of 2-


chloroethanol with concentrated NaOH solution. The reaction follows
intramolecular synthesis and follows SN2 synthesis
Reactions
a) Hydrolysis in acidic medium- formation of ethylene glycol
b) Reaction with halogen acids- formation of ethylene halohydrins
c) Reaction with Hydrogen cyanide- formation of ethylene
cyanohydrin
d) Reaction with organic acids- formation of glycol monoacetate
e) Reaction with alcohols- formation of glycol monoalkyl ether
f) Reaction with ammonia and its derivatives- formation of
substituted 2- aminoethanol
g) Reaction with Grignard reagent or alkyl lithiums followed by
hydrolysis- formation of 1˚ alcohols
h) Reaction with hydrogen- formation of ethanol
i) Action of heat- formation of ethanal
Rex are summarized as follow:
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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