Ethers: By: DR Saima Najm

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ETHERS

By: Dr Saima Najm


PhD Pharm. Chem.
Assistant Professor
L.C.P.S
NOMENCLATURE COMMON SYSTEM OF
NAMING
◦ In common system of naming ethers (simple and mixed),
ethers are named by naming the two groups bonded to oxygen
followed by the word ether.
For example:
◦ CH3-O-CH3 Dimethyl ether
◦ C2H5-O-CH3 Ethyl methyl ether
◦ C2H5-O-C2H5 Diethyl ether
◦ C6H5-O-CH3 Phenyl methyl ether
NOMENCLATURE IUPAC SYSTEM OF
NAMING
◦ In IUPAC system, large alkyl group is take as parent
molecule and given the last name (suffix) while the smaller
alky group along with oxygen is used as a prefix and given
the name ALKOXY
(e.g methoxy, ethoxy, propoxy etc)
◦ CH3-O-CH3 Methoxy methane
◦ C2H5-O-CH3 Methoxy ethane
◦ C2H5-O-C2H5 Ethoxy ethane
◦ C6H5-O-CH3 Methoxy benzene
PREPARATION OF ETHERS
1. WILLIAMSON’S SYNTHESIS (CONVERSION OF
ALCOHOLS INTO ETHERS)
The reaction of primary alcohol with sodium gives an alkoxide

2CH3CH2OH + 2Na 2CH3CH2O-Na+

Alkoxide when treated with RCl forms ether

CH3CH2O-Na+ + CH3CH2Cl CH3CH2-O-CH3CH2 + NaCl


2. REACTION OF ALKYL HALIDE WITH DRY SILVER
OXIDE
When alkyl halides are heated with dry silver oxide, ethers are
produced.

2C2H5Br + Ag2O C2H5-O-C2H5 + 2AgBr


3. DEHYDRATION OF ALCOHOLS
Ethers can be prepared by heating excess of alcohol with
conc. H2SO4 at 140°C
2CH3CH2OH CH3CH2-O-CH3CH2 + H2O

When alcohols are of different types, then mixed ethers can be


prepared.
𝐶𝑜𝑛𝑐.𝐻2𝑆𝑂4
140 °𝐶

CH3OH + CH3CH2OH CH3-O-CH3CH2 + CH3-O-CH3 +


CH3CH2-O-CH3CH2 + H2O
PHYSICAL PROPERTIES OF ETHERS
1. Ethers are colorless, highly inflammable compounds of low
boiling points
2. Their chemical inactivity and their ability to dissolve fats, oil, gums
and many more other organic compound make them very good
solvent
3. Ethers are soluble in conc. sulfuric acid. This property is used as a
distinguishing test between ethers and saturated hydrocarbons.
4. Lower ethers act as anesthetics
5. Ethers are lighter than water
CHEMICAL PROPERTIES OF ETHERS

The ethereal O atom is a region of high electron density due to


lone pairs
Ether O atom are Lewis bases, like an alcohol –OH group, the
–OR group is a poor leaving group and needs to be converted to a
better leaving group before substitution can occur.
Resistance to Oxidations: Ethers are resistant to attack by the
usual chemical oxidizing agent. Reagents like NH3, Na, alkali and
acids have no action on ethers
REACTION OF ETHER WITH HI AND HBr
The most important reaction of ether is cleavage by acids such
as HI and HBr

Reaction with HBr: The O atom of ether possess an unshared


electron pair which accepts a proton from HBr to form
Oxonium ion. No further reaction takes place.
R2O + HBr  R2O+ -H + Br-

Reaction with HI: The O atom of ether accepts a proton from


HI to form oxonium ion, which reacts with I- to form R-OH and
RI
R2O + HI  R2O+-H + + I- R2O+-H + + I-  R-OH + RI

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