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Ethers

The document summarizes key information about ethers including their properties, preparation methods, and reactions. It notes that ethers are weakly polar functional isomers of alcohols. Their boiling points are typically lower than similar alcohols and increase with molecular weight but decrease for branched isomers. Common preparation methods include the use of concentrated sulfuric acid to form symmetric ethers via an SN2 reaction, and the Williamson ether synthesis to form unsymmetric ethers using alkoxides in an SN2 reaction. Acidic cleavage and epoxide reactions are also discussed.

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151 views6 pages

Ethers

The document summarizes key information about ethers including their properties, preparation methods, and reactions. It notes that ethers are weakly polar functional isomers of alcohols. Their boiling points are typically lower than similar alcohols and increase with molecular weight but decrease for branched isomers. Common preparation methods include the use of concentrated sulfuric acid to form symmetric ethers via an SN2 reaction, and the Williamson ether synthesis to form unsymmetric ethers using alkoxides in an SN2 reaction. Acidic cleavage and epoxide reactions are also discussed.

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Ethers

functional isomer of alcohol

ELEMENTARY ORGANIC CHEMISTRY

CH2

CH3

ETHERS

H3C

CH2

H2C

LECTURE

C H
H

weakly polar
Boiling point

weakly polar
Boiling point

Ethanol
Dimethyl ether

OH

H3C

C
H
H
C
3
3
O

increases with increasing MW

Molecular weight BP, C

H2
C

Physical Properties

Propane

CH2

Physical Properties

Lower than to alcohols of similar MW

CH3

>

44

-42

46

78.5

46

-24

>

44

21

1-propoxypropane (MW = 46) 2-(propan-2-yloxy)propane (MW = 46)


BP = 90.5C
BP = 68C

methoxymethane (MW = 46)


BP = -24.9C

ethoxyethane (MW = 74)


BP = 34.6C

for isomeric ethers, decreases with branching

Ethanal
H

Physical Properties

Preparation of Ethers

weakly polar
Solubility in water

Formation of symmetric ethers

comparable to alcohols of similar MW


decreases with increasing MW

Reagent: conc. H2SO4


only for 1 ROH (formation of alkenes if 2 or 3 ROH)
Mechanism: SN2

<
methoxymethane (MW = 46)

ethoxyethane (MW = 74)

for isomeric ethers, increases with branching

<
1-propoxypropane (MW = 46) 2-(propan-2-yloxy)propane (MW = 46)

Preparation of Ethers

Preparation of Ethers

Williamson Ether Synthesis

Williamson Ether Synthesis

can be used to form unsymmetric ether


Reagent: alkoxide
Substrate: best for 1 RX (formation of alkenes if 3 RX,
no reaction if ArX)
Mechanism: SN2
Example:

Mechanism: SN2
Example:

Preparation of Ethers

Exercises

Williamson Ether Synthesis


How to produce alkoxide? (RECAP: acidity of ROH and
ArOH
ROH with a metal
ROH with a metal hydride
ArOH with NaOH

1. Draw a functional isomer


with a higher boiling point.

H 3C
O
H 3C

Exercise

Chemical Reactions

Propose a mechanism for the synthesis of the following


molecules.

Acidic cleavage

O
H
CC
H
2
3
O

Reagent: strong acid at elevated temperature


General:
R-O-R + HX R-X + R-OH
Mechanism:
SN1 if R is benzylic, allylic, or 3
SN2 if R is CH3, 1, 2

R-OH cannot react with another mol of HX if R is Ar


R-OH + HX R-X + H2O

Chemical Reactions

Epoxides (oxiranes)

Acidic cleavage

3-membered cyclic ethers


H
C
2

C
H
2

O
ethylene oxide

How to prepare oxiranes?


Reaction of alkene with mCpBA
Halohydrin formation, followed by intramolecular
nucleophilic substitution

Reactions of Epoxides

Reactions

Acid-Catalyzed Ring Opening


follows SN1 mechanism => formation of the more
stable carbocation

Base-Catalyzed Ring Opening

CH3

CH3
H3C

C H

CH3OH
CH2

follows SN2 mechanism => base attacks the less


substituted C

H+

H3C

CH2OH

H 3C

C H
O

OCH3

C H

C H 3O C H 3O H

H 3C

C
O H

C H 3O C H

OH

1.

Exercises

OH

2.

H2SO4, 140

H 3C

C H 2C H 3

K M nO 4

O
C
H
3
C
H
2
O
(
H
C
)
C
3
3

H
+

C
H
2
O
(
H
C
)
C
3
3

N a

3.
O H

H
B
r

C H 3C H 2C H 2C l

C
H
3
C

3 . v ia w h a t m e c h a n is m ?

C
H
3
O
C

CH3

4.

C
H
3

CH3

H2
C

C
H
3
C
H
2
O
-

C
CH3

HCl(in excess)

C
H
3
C
H
2
O
H

C
H
3

OH

1.

H 2 S O 4 , 1 4 0

N a

2.
O H

C H 3C H 2C H 2C l
3 . v ia w h a t m e c h a n is m ?
4. m ost acidic
OCH3

Cl

OH

L ew is

OH

M ike

H arvey

1 . (2 p ts)

H O

K 2C r2O
H

2 . (2 p ts)

H 3C

OH

C H 2C H 3

K M nO 4

3. (3 pts)

HBr (excess)

CH3

4. (4 points)

CH3

H2
C

C
O

CH3

HCl(in excess)

NaOCH3 / CH3OH

1. (3pts)

OCH2CH3

2. (2pts) ?
HO

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