Chapter 1 Alcohols and Ethers

Table of Contents

Introduction
1. Classification of Alcohols
2. Nomenclature of Alcohols
3. Physical Properties of Alcohols
4. Chemical Properties of Alcohols
5. Preparation of Alcohols
6. Some Important Alcohols
 Chapter 1 Alcohols and Ethers

Table of Contents

7. Introduction to Ethers
8. Nomenclature of Ethers
9. Physical Properties of Ethers
10. Chemical Properties of Ethers
11. Preparation of Ethers
12. Diethyl Ether
 Chapter 1 Alcohols and Ethers

Warm Up

• List down some uses of alcohols in your lives.

• What are the benefits and harms of alcohols that you

know.

• In industry how is alcohol produced?

 Chapter 1 Introduction to Alcohols

• Compounds in which the hydroxyl group is bonded to an

alkyl group are called alcohols. They are known as alkyl
derivative of water.
• R–H H – OH R – OH
alkane water alcohol

OH
OH
H2
H3C OH H3C C C CH3
H
Methyl Alcohol Isobutyl Alcohol
cyclopropyl alcohol
 Chapter 1 Introduction to Alcohols
H2 OH
OH OH
C

H2C C CH2
H phenol
propenyl alcohol benzyl alcohol not alcohol

OH OH O
H2C H2 H2
CH C C C R C OH
ethenol not alcohol
not alcohol OH
not alcohol
 Chapter 1 1. Classification of Alcohols

A. According to The number of –OH Groups

1. Monohydric Alcohols
CH3OH CH3CH2OH
methyl alcohol ethyl alcohol

OH

CH3CH2CH2OH
CH
propyl alcohol H3 C CH3
2-propa nol
 Chapter 1 1. Classification of Alcohols

A. According to The number of –OH Groups

2. Polyhydric Alcohols
HO OH OH OH OH

H2 C CH2 H2 C CH CH2

1,2 e tha ne diol 1,2, 3 propa ne triol

glycol glyce rol

OH OH
H2
H2 C CH C CH3
1,2 buta ne diol
 Chapter 1 1. Classification of Alcohols
B. According to The Carbon Atom Having
The –OH Group
1. Primary (1o)Alcohols

H
R C OH
H
H H3C
Primary H 3C C OH

H H2C CH2 OH
Ethyl alcohol
1o Propyl alcohol
 Chapter 1 1. Classification of Alcohols
B. According to The Carbon Atom Having
The –OH Group
2. Secondary (2o)Alcohols
R' CH3
R C OH
H3C C OH
H
Secondary H
2o propyl alcohol
CH3
H2
H 3C C CH OH
2-butanol, 2o butanol
 Chapter 1 1. Classification of Alcohols
B. According to The Carbon Atom Having
The –OH Group
3. Tertiary (3o)Alcohols
R' CH3
R C OH
H3C C OH
R" CH3
Tertiary H3 C
CH3
3o butyl alcohol H2 C C OH

CH3
tertiary pentanol
 Chapter 1 1. Classification of Alcohols
Example 1
Which of the following is an alcohol?
OH
A.
H B.
C
HO O

C. NaOH D. CH3

CH
H3 C OH
 Chapter 1 1. Classification of Alcohols
Solution
Which of the following is an alcohol?
OH
A.
H B.
C
HO O

C. NaOH D. CH3

CH
H3 C OH
 Chapter 1 1. Classification of Alcohols
Example 2
Which of the following is not an alcohol?
OH
OH
A.
B. OH
CH
H3C CH2

OH
OH
C. D. CH3 CH3
C
H3 C CH H3C C CH2

OH OH
 Chapter 1 1. Classification of Alcohols
Solution
Which of the following is not an alcohol?
OH
OH
A.
B. OH
CH
H3C CH2

OH
OH
C. D. CH3 CH3
C
H3C CH H3C C CH2

OH OH
 Chapter 1 1. Classification of Alcohols
Example 3
Which of the following is a monohydric alcohol?
OH
OH
A.
B. OH
CH CH3
H3C CH

OH
OH
C. D. CH3 CH3
CH
H2 C CH2 H3C C CH

OH OH CH3
OH
 Chapter 1 1. Classification of Alcohols
Solution
Which of the following is a monohydric alcohol?
OH
OH
A.
B. OH
CH CH3
H3C CH

OH
OH
C. D. CH3 CH3
CH
H2C CH2 H3C C CH

OH OH CH3
OH
 Chapter 1 1. Classification of Alcohols
Example 4
Which of the following is a polyhydric alcohol?
OH
OH
A.
B.
CH
H3C CH2

OH
OH
C. D. OH CH3
C
H2C CH H3C C CH

OH OH CH3
OH
 Chapter 1 1. Classification of Alcohols
Solution
Which of the following is a polyhydric alcohol?
OH
OH
A.
B.
CH
H3C CH2

OH
OH
C. D. OH CH3
C
H2C CH H3C C CH

OH OH CH3
OH
 Chapter 1 1. Classification of Alcohols
Example 5
Which of the followings are tertiary alcohols?

OH OH CH3 OH
A.
B. C. CH C
CH H2C
H3C CH2 CH2 H2 C CH CH3
CH3
OH CH3 OH OH

OH
D. CH3
E. CH3 F.
OH
C
H2C CH2 H3C CH CH

OH OH CH3
OH
 Chapter 1 1. Classification of Alcohols
Solution
Which of the followings are tertiary alcohols?

OH OH CH3 OH
A. 3o
o B. 1o C. CH 2o C
CH 1 H2C
H3C 2o CH2 CH2 H2 C o CH CH3
1
CH3
OH CH3 OH OH

OH
D. CH3
E. CH3 F.
OH
2o C 1o
2o
H2C o
3 CH2 2o
H3C CH CH

OH OH CH3
OH
 Chapter 1 2. Nomenclature of Alcohols
• Common names are used for simpler alcohols. Common
names are derived by naming the alkyl group attached to
the –OH group and then the word “alcohol” is added.
H3C OH H2 CH3
Methyl Alcohol H 3C C OH
Ethyl Alcohol
H3C CH OH

CH3 Isopropyl Alcohol

H3C C OH

CH3
tert buthyl Alcohol
 Chapter 1 2. Nomenclature of Alcohols
According to IUPAC system;
• Change last letter “–e” with “–ol” in the alkane name of
longest carbon atom chain in which hydroxyl group is
bonded.
• Number the carbon atoms in the chain starting from
nearer to the hydroxyl group. Indicate the position of the
hydroxyl group by using number.
• If there are more than one –OH group, use “di, tri,
tetra…” before –ol . Br OH
CH3 OH
H2C 3 CH
4 CH 2 CH3
CH 3 CH
4 1
H 3C C 2 CH3
5 H2 1 CH3
4-methyl 2-pentanol 4-bromo-3-methyl 2-butanol
 Chapter 1 2. Nomenclature of Alcohols
OH OH
H2
C CH2 H3C CH
C CH CH3
H2
3-cyclopentyl 1-propanol NH2
3-amino 2-butanol

CH3 OH CH3 OH

CH C CH CH Cl
H2 C C CH3 H2C CH CH
H2
CH3
OH
OH OH CH3
2, 4-dimethyl 1, 4-pentanediol 5-chloro-2-methyl 1,3,4-hexanetriol
 Chapter 1 2. Nomenclature of Alcohols
Example 6
Name the following structures according to IUPAC system.

OH
OH B.
A. H3C CH
H2
C CH2 CH CH3
Cl C
H2

OH
C.
OH
H3C CH D.
CH CH3 H2C CH
C CH3
OH H
 Chapter 1 2. Nomenclature of Alcohols
Solution
Name the following structures according to IUPAC system.
OH
B.
OH
A. H2
H3C CH
CH CH3
C CH2
Cl C
H2
3-chloro 1-propanol
3-phenyl 2-butanol
OH
C.
OH
H3C CH D.
CH CH3 H 2C CH
C CH3
OH H
2, 3-butanediol 3-butene-2-ol
 Chapter 1 2. Nomenclature of Alcohols
Example 7
Which of the following structures is named wrongly?

A.
OH B. OH
H2 H2
C CH C CH
H2N C CH3 H3C CH CH3
H2
3-amino 2-butanol

C. OH 3-cyclobutyl 2-pentanol
H2 D.
C CH2
OH
Br CH H3C C
C C
OH H2
2-butene-1-ol
1-bromo 2, 3-propanediol
 Chapter 1 2. Nomenclature of Alcohols
Solution
Which of the following structures is named wrongly?
OH B. OH
A. H2 H2
C CH
C CH H3C CH CH3
H2N C CH3
H2
4-amino 2-butanol
C. OH 3-cyclobutyl 2-pentanol
D.
H2
C CH2 OH
Br CH H3C C
C C
H2
OH 2-butene-1-ol
1-bromo 2, 3-propanediol
 Chapter 1 2. Nomenclature of Alcohols
Example 8
What is the correct name for the following structure?

OH

A. 1-bromo-2-methyl 3-cyclopentanol
H3C
B. 1-bromo-2-methyl 3-pentanol
C. 2-methyl-3-bromo 1-cyclopentanol
Br D. 3-bromo-2-methyl 1-cyclopentanol
 Chapter 1 2. Nomenclature of Alcohols
Solution
What is the correct name for the following structure?

OH
A. 1-bromo-2-methyl 3-cyclopentanol
H3C
B. 1-bromo-2-methyl 3-pentanol
C. 2-methyl-3-bromo 1-cyclopentanol
Br D. 3-bromo-2-methyl 1-cyclopentanol
 Chapter 1 2. Nomenclature of Alcohols
Example 9
Which of the following is 2, 3, 4-trimethyl 1-hexanol?
A. CH3 CH3 B. CH3
H2 H2
HO CH CH CH3 C CH C
C C CH H3C CH CH OH
H2 H2
CH3 CH3 CH3

C. CH3 CH3 D. CH3 CH3

CH CH CH3 CH CH CH3
H3C CH CH H 3C C CH
H2
OH CH3 OH
 Chapter 1 2. Nomenclature of Alcohols
Solution
Which of the following is 2, 3, 4-trimethyl 1-hexanol?
A. CH3 CH3
B. CH3
HO CH CH CH3 H2 H2
C CH C
C C CH
H2 H2 H3C CH CH OH
CH3
CH3 CH3

C. CH3 CH3
D. CH3 CH3
CH CH CH3
H3C CH CH CH CH CH3
H 3C C CH
H2
OH CH3
OH
 Chapter 1 2. Nomenclature of Alcohols
Example 10
Which of the following is the isomer of 2, 3-dimethyl 2-butanol?
A. CH3 B. CH3
OH OH
HO CH CH3 H 3C CH CH3
C C C C
H2 H2
CH3 CH3

C. CH3 D. CH3
OH
OH CH3
C
C CH3 H3C C
H3C C
H H 3C
CH3 CH3
 Chapter 1 2. Nomenclature of Alcohols
Solution
Which of the following is the isomer of 2, 3-dimethyl 2-butanol?
A. CH3 B. CH3
OH OH
HO CH CH3 H 3C CH CH3
C C C C
H2 H2
CH3 CH3

C. CH3 D. CH3
OH OH
C CH3 C CH3
C H3C C
H3C
H H 3C
CH3 CH3
 Chapter 1 3. Physical Properties of
Alcohols

• Alcohols have both polar and non polar parts in their

structures.
• C1 to C11 are colorless and have characteristic smell.
• Water soluble, solubility decreases with increasing chain
length. But increases with branching.
• Boiling points of alcohols increase with increasing
molecular weight and the number of hydroxyl group in
the molecule.
 Chapter 1 4. Chemical Properties of
Alcohols

• In the first group of reactions alcohols may serve as

acids (proton donors) and they dissociate in manner
similar to water.

R O H R O + H
alcohol alkoxide ion

• Salt formation: Alcohols form salts with active metals

such as Na, K,.. etc.
R O H + Na R ONa + 1/2H2
Chapter 1 4. Chemical Properties of
Alcohols
 Chapter 1 4. Chemical Properties of
Alcohols

• Ester formation: In the presence of an acid catalyst,

alcohols react with acids to form esters.
O O
H2SO4
ROH + R' C OH R' C OR + H2O

O O
H2SO4
C2H5OH + OH C CH3 C 2 H 5O C CH3 + H2O
ethanol acetic acid ethyl acetate
 Chapter 1 4. Chemical Properties of
Alcohols
• Inorganic acids also form esters with alcohols. Such as
the esterification of glycerol with HNO3 forms glyceryl
trinitrate, is an explosive ingredient in dynamite.

H 2C OH H 2C ONO2

HC OH + 3HONO2 HC ONO2 + 3H2O

H2C OH H 2C ONO2
1,2,3-propanetriol glyceryl trinitrate
(glycerol) (nitroglycerine)
 Chapter 1 4. Chemical Properties of
Alcohols

• In the second group of reactions hydroxyl group is

replaced. First type is conversion of alcohols to alkyl
halides.
R O H + H-X R X + H2 O

• Second type is dehydration.

H2 H2SO4 H
R C OH R C CH2 + H2O
alkene
 Chapter 1 4. Chemical Properties of
Alcohols

• Third type is oxidation of alcohols. KMnO4 and K2Cr2O7

oxidize 1o and 2o alcohols, 3o alcohols cannot be oxidized.
O
H2SO4
C2H5OH + K2Cr2O7 OH C CH3
acetic acid

OH O
NaOH
CH3CHCH3 + KMnO4 CH3CHCH3
Isopropyl alcohol Acetone
 Whether a thing is a good or bad it
depends upon us. Fire is a good thing
to warm up, but can it be said it is bad
when we put our hands in it?
 Chapter 1 4. Chemical Properties of
Alcohols
Example 11
Arrange the following compounds in order of increasing
solubilities.
OH
A. H2 H2
H3C C CH3 B. H2 C C CH3

OH
C. D. CH3
CH
H2C CH2 H3C CH CH CH3

OH OH OH
 Chapter 1 4. Chemical Properties of
Alcohols
Solution
Arrange the following compounds in order of increasing
solubilities.
OH
A. H2 H2
H3C C CH3 B. H2 C C CH3

OH
C. D. CH3
CH
H2C CH2 H3C CH CH CH3

OH OH OH

A<B<D<C
 Chapter 1 4. Chemical Properties of
Alcohols
Example 12
Which of the following has the highest boiling point?

OH OH
A. H2
H3C C CH3 B. H2 C C CH3
H

C. H2 D.
HO OH OH
H2C C CH2
H2 C C CH2
OH OH H
 Chapter 1 4. Chemical Properties of
Alcohols
Solution
Which of the following has the highest boiling point?

OH OH
A. H2
H3 C C CH3 B. H2C C CH3
H

C. H2 D.
HO OH OH
H2C C CH2
H2C C CH2
OH OH H
 Chapter 1 4. Chemical Properties of
Alcohols
Example 13
Which of the following alcohol has the highest melting point?

HO OH
A. H2 H2 H2
H3 C C CH2 B. H2C C C CH3

H2 H2
C. C C
D. OH
H2C C CH3
H2 H3C CH2
OH
 Chapter 1 4. Chemical Properties of
Alcohols
Solution
Which of the following alcohol has the highest melting point?

HO OH
A. H2 H2 H2
H3C C CH2 B. H2 C C C CH3

H2 H2
C. C C
D. OH
H2C C CH3
H2 H3C CH2
OH
 Chapter 1 4. Chemical Properties of
Alcohols
Example 14
How many liters of hydrogen gas is produced at STP, when
2.3 g of sodium is put into excess ethanol?

A. 1.12 B. 2.24 C. 4.48 D. 8.96

Solution
CH3CH2OH + Na  CH3CH2ONa + ½ H2
 Chapter 1 4. Chemical Properties of
Alcohols
Example 15
Predict the result of following reactions.
HO
A. H2
H3C C CH2 + HCl

OH
B. H2 H2SO4
H3C C CH2
 Chapter 1 4. Chemical Properties of
Alcohols
Solution
Predict the result of following reactions.
HO Cl
A. H2 H2
H3C C CH2 + HCl H3C C CH2
+ H 2O
1-chloro propane

OH
B. H2 H2SO4
H
H3C C CH2 H3 C C CH2
Propene
 Chapter 1 4. Chemical Properties of
Alcohols
Example 16
What are the result of following oxidation reactions.
H2
A. C OH
H3C CH
+ KMnO4 H+
CH3

B. H2 H2
C C
H3 C C OH + K2Cr2O7 H+
H2

C. H2 CH3
C CH3
H3C C + K2Cr2O7 H+

OH
 Chapter 1 4. Chemical Properties of
Alcohols
Solution
What are the result of following oxidation reactions.
H2
A. C OH H2
H3C o CH + KMnO4 H+ C CH3
2 H3C C
CH3
O
Ethyl methyl ketone
B. H2 H2 O
C C H2
H3C C OH + K2Cr2O7 H+ C C
o
H2 1 H3 C C OH
H2
butanoic acid
C. H2 CH3
C CH3
+ K2Cr2O7 H+
H3C C
3 o No reaction
OH
 Chapter 1 4. Chemical Properties of
Alcohols
Example 17
Write the equations for each of the following.

A. n-propyl alcohol to propene

B. n-butyl alcohol to butanoic acid

C. 2-pentanol to diethyl ketone

D. t-butyl alcohol to t-butyl bromide

E. Isobutyl alcohol to methyl ethyl ketone

 Chapter 1 4. Chemical Properties of
Alcohols
Solution
Write the equations for each of the following.
H2 OH
A. C H
H3 C C
H2SO4 C
H2 H3 C CH2
o
n-propyl alcohol 180 C propene

B.
H3C
OH H2
+ H3C O H2 O
H2 H C H3C
H2C C CH2 [O] C
C C C C OH
K2Cr2O7 H2 H H2
n-butyl alcohol butanoic acid
butanal
 Chapter 1 4. Chemical Properties of
Alcohols
Solution
Write the equations for each of the following.
H2 H2 H2 H2
C. C C K2Cr2O7 C C
H3 C CH CH3 H3C C CH3
H2SO4
OH O
2-pentanol diethyl ketone

D. OH Br

H3C C CH3 + HBr H3C C CH3 + H2O

CH3 CH3
t-butyl alcohol t-butyl bromide
 Chapter 1 4. Chemical Properties of
Alcohols
Solution
Write the equations for each of the following.

E. H2
H3C C KMnO4 H2
CH CH3 H3C C
NaOH C CH3
OH
O
isobutyl alcohol methyl ethyl ketone
 Chapter 1 4. Chemical Properties of
Alcohols
Example 18
How many liters of ethylene at STP can be prepared from
40 g of 92% ethyl alcohol by 70% yield?
OH
H2SO4
H3C CH2 H2C CH2 92
mass of ethanol (pure) = x 40
ethyl alcohol 180o ethylene 100
46 g 22.4 L = 36.8 g
only 70% of 36.8 g of ethanol can be converted to ethylene.
70 x 36.8 g = 25.76 g.
Then, mass of ethanol reacted =
100
Since 46 g of ethanol produces 22.4 L of ethylene,
25.76 x 22.4
25.76 g of ethanol produces X =
46
= 12.5 L of ethylene
 Chapter 1 5. Preparation of Alcohols

A. Hydration of Alkenes
OH

Cold
R C CH2 + H2 O CH
H H2SO4
R CH3

B. Hydrolysis of Alkyl Halides

R X + NaOH R OH + NaX
 Chapter 1 5. Preparation of Alcohols

C. Using Grignard reagent

• Preparation of primary alcohols.

H
R MgCl +H C O R C OMgCl
H H
formaldehyde grignard reagent

H H
R C OMgCl + H 2O R C OH + Mg(OH)Cl
H H
primary alcohol
 Chapter 1 5. Preparation of Alcohols

C. Using Grignard reagent

• Preparation of secondary alcohols.

R
R MgCl + R C O R C OMgCl
H H
Aldehyde
R R
R C OMgCl + H2O R C OH + Mg(OH)Cl
H H
secondary alcohol
 Chapter 1 5. Preparation of Alcohols

C. Using Grignard reagent

• Preparation of tertiary alcohols.

R
R MgCl + R C O R C OMgCl
R R
Ketone
R R
R C OMgCl + H 2O R C OH + Mg(OH)Cl
R R
tertiary alcohol
 Chapter 1 5. Preparation of Alcohols

Example 19
Perform the following transformations.

A. ………  1-propanol

B. ………  isobutanol

C. ………  ter-butanol
 Chapter 1 5. Preparation of Alcohols

Solution
Perform the following transformations.
A. H2
H3C C H2
C Cl + NaOH H 3C C
H2 C OH + NaCl
1-chloro propane H2
1-propanol
OH
B. Cold
H
H 3C C CH2 + H2 O H3C CH
C
H2 H2SO4 C CH3
H2
1-butene
isobutanol
 Chapter 1 5. Preparation of Alcohols

Solution
Perform the following transformations.

C. CH3
H3C MgCl + H3C C O H 3C C OMgCl
CH3 CH3
Acetone

CH3 CH3
H 3C C OMgCl + H2O H3C C OH + Mg(OH)Cl
CH3 CH3
ter-butanol
 Chapter 1 5. Preparation of Alcohols

Example 20
What is the result of following reaction?

Chloro cyclobutane + NaOH  ……………

Solution

Cl OH

+ NaOH + NaCl
chloro cyclobutane cyclobutanol
 Chapter 1 5. Preparation of Alcohols

Example 21
Which alcohol and how many grams are produced by the
hydration of 9.6 g of 2-butene?
Solution
H3C CH3
H3C CH3
H2SO4
+ H-OH H2C C OH
HC CH cold H
2-butene 2-butanol

56 g 74 g

If 56 g of 2-butene produces 74 g of 2-butanol

9.6x74
9.6 g of 2-butene produces X=
56
= 12.7 g
 Chapter 1 6. Some Important Alcohols

1. Methyl Alcohol

• It is colorless, flammable, and

has characteristic odor.
• It is highly toxic, can cause blindness, large quantities
cause death. To prevent poisoning pyridine is added.
• It can be used as antifreeze in radiators.
• It is soluble in water and organic solvents, and can also
dissolve fats and resins.
• It is the most acidic member of monohydric alcohols.
 Chapter 1 6. Some Important Alcohols

1. Methyl Alcohol
• It can easily burn with a bluish flame.
• It can be easily oxidized to formaldehyde and CO2.
• It is also called wood alcohol. Because it is first obtained
from the distillation of wood.
• In industry it is produced from water gas (CO + H2) under
high pressure and temperature in the presence of catalyst.
• About 40% of methanol production is converted to
formaldehyde, and from there into products as diverse as
plastics, plywood, paints, explosives, and permanent press
textiles.
ZnO-Cr2O3
CO + 2H2 CH3OH
300-400oC, 200 atm methanol
 Chapter 1 6. Some Important Alcohols

2. Ethyl Alcohol

• It is colorless, soluble in water and

has a characteristic smell, affecting
the central nervous system.
• 95% of its solution is called ethyl alcohol, used in laboratories.
• 100% pure ethyl alcohol is named as absolute alcohol.
• It is a important organic solvent, used in the preparation of
tincture of iodine, paints, essence, perfumes and cosmetics.
• In medicine it is used as disinfectant.
• It is commonly prepared from grape juice by fermentation.
Chapter 1 6. Some Important Alcohols

2. Ethyl Alcohol
Chapter 1 6. Some Important Alcohols

2. Ethyl Alcohol
 Chapter 1 6. Some Important Alcohols

Preparation of Ethyl Alcohol

Yeast
C12H22O11 + H 2O 4CH 3CH2OH + 4CO2
sucrose ethanol
Yeast
C6H12O6 2CH3CH2OH + 2CO2
glucose ethanol

CaC2 + 2H2O Ca(OH)2 + HC CH

H2SO4 acetylene
HC CH + H2O H 3C C O
HgSO4 H
acetaldehyde
Cu or Ni
H 3C C O + H 2 CH3CH2OH
H
ethanol
 Chapter 1 6. Some Important Alcohols

3. Glycol

• Alcohols containing two –OH

groups are called gylcols. The most
common glycol is ethylene glycol, C2H4(OH)2.
• It is colorless, odorless, syrupy liquid, completely miscible in
water. Since it has low melting point it is used as antifreeze in
radiators.
• It is also used in hydraulic brake fluid in cars, as a liquid, oil, ink
and resin solvent.
 Chapter 1 6. Some Important Alcohols

4. Glycerin or Glycerol

• The simplest trihydric alcohol,

C3H5(OH)3.
• It is colorless, odorless, syrupy liquid, soluble in water,
methanol and ethanol. It absorbs moisture well.
• It is used in the production of dynamite, invented by Alfred
Nobel, a Swedish scientist.
• It is also used in tobacco, shaving and toilet soaps, cosmetics,
lotions, ointments, antifreeze, cellophane, printing-press ink.
• It is produced from fats and oils in basic medium.
Chapter 1 6. Some Important Alcohols

4. Glycerin or Glycerol
 Chapter 1 7. Introduction to Ethers

• Ethers are alcohol derivatives resulting from the condensation

of alcohols.
• General formula is CnH2n+2O

O O O
H H R H R R'
water alcohol ether

H3C O CH3 H3C O C 2 H5

simple(symmetric) ether complex(asymmetric) ether
 Chapter 1 8. Nomenclature of Ethers

• First name the groups attached to oxygen atom in

alphabetical order, and then read the word “ether”.
• If the groups are symmetric, use –di before the name of the
group.
Example 22
H3C O C CH2 O
H
CH3 methyl vinyl ether diphenyl ether
C2H5 O CH

CH3 C2H5 O C 2 H5 O CH3

ethyl isopropyl ether diethyl ether
methyl phenyl ether
 Chapter 1 9. Physical Properties of Ethers

• Bond angle is not equal to 180o in R-O-R, they have a limited

polarity.
• They are more volatile than their corresponding alcohols.
• Boiling point increases by the increasing molecular weight.
Branching lowers the boiling point.
• Since ethers are polar they are soluble in many polar and
non polar substances very well.
 Chapter 1 10. Physical Properties of Ethers

• Chemically ethers resemble alkanes rather than alcohols or

water.
• When ethers are heated with concentrated strong acid
halides they undergo decomposition reactions.

R-O-R + H-X → R-O-H + R-X

Example 22

C2H5-O-C2H5 + H-Cl → C2H5-OH + C2H5-Cl

 Chapter 1 11. Preparation of Ethers

1. Dehydration of Alcohols
H2SO4
2R OH o R-O-R + H2O
alcohol 140 C ether

2. The Williamson Synthesis of Ethers

R-X + R-O-Na+ R - O -R + NaX

Example 23
H2SO4
2C2H5-OH → C2H5 -O- C2H5 + H2O
140oC
C2H5-Cl + C2H5-ONa → C2H5 -O- C2H5 + NaCl
 Chapter 1 12. Diethyl Ethers

• The most commonly known ether

• Colorless, volatile, flammable liquid
with characteristic odor.
• Causes fainting when inhaled, used in medicine as an
anesthetic.
• Good solvent for organic substances.

H2SO4
2C2H5-OH → C2H5 -O- C2H5 + H2O
140oC
End of the chapter 1