Scribd
Upload
13 views

Introduction-to-Ethers (1)

Ethers are organic compounds characterized by an ether group (R-O-R') and are commonly used as solvents and reagents in various industries, including pharmaceuticals. They exhibit unique physical properties, such as lower boiling points than alcohols, and can undergo reactions like acid cleavage and peroxide formation. Key preparation methods include Williamson ether synthesis and acid-catalyzed dehydration, with safety precautions necessary due to potential peroxide formation.

Uploaded by

sarun.parajuli
Copyright
© © All Rights Reserved
We take content rights seriously. If you suspect this is your content, claim it here.
Available Formats
Download as PDF, TXT or read online on Scribd
13 views

Introduction-to-Ethers (1)

Ethers are organic compounds characterized by an ether group (R-O-R') and are commonly used as solvents and reagents in various industries, including pharmaceuticals. They exhibit unique physical properties, such as lower boiling points than alcohols, and can undergo reactions like acid cleavage and peroxide formation. Key preparation methods include Williamson ether synthesis and acid-catalyzed dehydration, with safety precautions necessary due to potential peroxide formation.

Uploaded by

sarun.parajuli
Copyright
© © All Rights Reserved
We take content rights seriously. If you suspect this is your content, claim it here.
Available Formats
Download as PDF, TXT or read online on Scribd
You are on page 1/ 8

Introduction to Ethers

Ethers are organic compounds with an ether group: an oxygen atom


connected to two alkyl or aryl groups (R-O-R'). The general formula is
R-O-R', where R and R' are alkyl or aryl groups.

They are common solvents and reagents in organic chemistry. Ethers


are also used in pharmaceuticals, polymers, and other industrial
applications. We'll cover nomenclature, physical properties, reactions,
and preparation.

by Sarun Parajuli
Nomenclature of Ethers
IUPAC Nomenclature Common Names Cyclic Ethers
Simple ethers are alkoxyalkanes Symmetrical ethers are dialkyl Cyclic ethers include oxiranes,
(e.g., CH3-O-CH3 is ethers (e.g., CH3-O-CH3 is oxetanes, furans, and pyrans.
methoxymethane). dimethyl ether). Unsymmetrical Examples are ethylene oxide
Unsymmetrical ethers are ethers are alkyl alkyl ether (e.g., (oxirane) and tetrahydrofuran
alkoxy derivatives (e.g., CH3-O- CH3-O-CH2CH3 is ethyl methyl (THF).
CH2CH3 is methoxyethane). ether).
Physical Properties of Ethers
Physical State Solubility

Ethers are typically liquids at room temperature, though Lower molecular weight ethers are slightly soluble in water
simple ethers are gases. due to hydrogen bonding. Solubility decreases with longer
alkyl chains. Diethyl ether has a solubility of ~6.9 g/100 mL
Boiling Points
at 20°C.
They have lower boiling points than alcohols of
Other Properties
comparable weight due to no hydrogen bonding. Similar to
alkanes of comparable weight. Diethyl ether boils at 34.6°C, Ethers are typically less dense than water. They are polar
while Butanol boils at 117.7°C. due to the C-O bond, but less polar than alcohols.
Chemical Reactions of Ethers
Overview
Ethers are generally unreactive due to their strong C-O bonds and
lack of acidic hydrogens.

Cleavage by Acids
Ethers can be cleaved by strong acids (HX, where X = Cl, Br, I).

Peroxide Formation
Ethers can form peroxides through auto-oxidation.

Reactions of Cyclic Ethers


Cyclic ethers, like epoxides, undergo unique reactions.
Cleavage by Acids
Reaction
Ethers react with strong acids (HI, HBr) to form alkyl
1 halides and alcohols: R-O-R' + HX ³ R-X + R'-OH. An
example is CH3-O-CH3 + HBr ³ CH3Br + CH3OH
(occurs at higher temperatures).

Mechanism
2 The acid protonates the oxygen, followed by SN1 or SN2
attack by the halide ion.

Reactivity Order
3 The reactivity order is HI > HBr > HCl.

Aryl Ethers
4 Aryl ethers need more vigorous conditions for cleavage
because of resonance stabilization.
Peroxide Formation

1 Auto-oxidation
Ethers react with oxygen to form explosive organic
peroxides: R-O-R' + O2 ³ R-O-O-H + R'" (radical
mechanism).

Risk
2
Peroxides can detonate when concentrated, distilled, or
subjected to mechanical shock.

3 Prevention
Store ethers with stabilizers (e.g., BHT) in dark bottles. Test
for peroxide presence before distillation.

4 Detection
Use peroxide test strips before distillation and discard old
ether containers.
Preparation of Ethers
Williamson Ether Synthesis Acid-Catalyzed Dehydration Epoxide Synthesis

Alkoxide ion reacts with a primary Heating alcohols with strong acid Epoxides are formed by oxidizing
alkyl halide or sulfonate: R-O- + R'-X (H2SO4) forms symmetrical ethers: 2 alkenes using peroxyacids (e.g.,
³ R-O-R' + X-. For example: R-OH ³ R-O-R + H2O (at 140°C). mCPBA).
CH3CH2-O-Na+ + CH3I ³ CH3CH2- Works best for primary alcohols, but
O-CH3 + NaI. Best for primary alkyl can lead to elimination at higher
halides to avoid elimination. temperatures.
Conclusion
Importance
Ethers are important organic compounds with unique
properties and reactivity.

Applications
They have uses as solvents, reagents, and pharmaceuticals.

Key Takeaways
Ethers have distinct nomenclature, physical properties, cleavage
reactions, and preparation methods (Williamson synthesis,
dehydration).

Safety
Handle ethers with care due to peroxide formation.

You might also like