CHEMISTRY GRADE 11

6.2 

At the end of this section, you will be able to:

) define alcohols
) tell the functional group of alcohols
) classify alcohols based on the number of hydroxyl groups
) write the general formulas of monohydric alcohols
) write the molecular formulas and the names of the first six members of
the monohydric alcohols
) give the IUPAC names for the given alcohols
) classify monohydric alcohols based on the number of alkyl groups
attached to the carbon atom carrying the hydroxyl group
) give some examples for primary, secondary and tertiary alcohols
) describe the physical properties of alcohols
) explain general methods of preparation of alcohols
) explain the industrial preparation of ethanol
) perform an experiment to prepare ethanol from sugar
) explain the chemical reactions of alcohols such as oxidation, reaction
with active metals, esterification and dehydration
) carry out an activity to show chemical reactions of alcohols with active
metals
) write the molecular formulas and names of the first six members of ethers
) give the IUPAC names for given ethers
) describe the physical properties of ethers
) explain the general methods of preparation of ethers
) explain the use of ethers, such as solvent inorganic reactions.

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Activity 6.1
Discuss the following questions in groups, and write a report. Present your
report to the class.
1. List some alcohols you know. Name the alcohol used in alcoholic
beverages. What are the uses of alcohols in industry?
2. Ethiopia uses an alcohol blended with gasoline to drive cars. What is the
name of the alcohol?
3. Hand sanitizers are used as an alternative to washing hands to kill most
bacteria and viruses that spread colds and flu. Which alcohol (s) is
present in hand sanitizers?
4. Explain the effects of using carbon-based fuels on the increase in carbon
dioxide in the atmosphere and its consequences.
What do you think when you hear the word “alcohol”? Can you define alcohol?

Give a few examples of the uses of alcohols. Most people think of two common
alcohols: the substance that intoxicates people, and the one used in clinics and
hospitals. However, there are many types of alcohol. The only alcohol present in all
alcoholic beverages is called ethanol. Other alcohols are used for different purposes.

Alcohols are derivatives of hydrocarbons in which one or more of the hydrogen

atoms in the hydrocarbon have been replaced by a hydroxyl group (–OH). The
functional group in an alcohol is an –OH (hydroxyl) group, which is responsible for
imparting certain chemical and/or physical properties to the compound. In alcohols,
the hydroxyl group is directly attached to carbon atom(s) of an aliphatic system.

Example 6.1

H H H H H H

H C OH H C C OH H C C C OH

H H H H H H

Methanol Ethanol 1-Propanol (Propan-1-ol)

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 CHEMISTRY GRADE 11

 
Alcohols may be classified as mono–, di–, tri- or polyhydric compounds depending
on whether they contain one, two, three or many hydroxyl (–OH) groups respectively
in their structures.
i. Monohydric alcohols are alcohols containing only one hydroxyl group.

Example 6.2

CH3 CH2 OH CH3 CH2 CH2 OH CH3 CH2 CH2 CH2 OH

Ethanol 1-Propanol 1-Butanol (Butan-1-ol)

Which one of the above monohydric alcohols is present in any drinking alcohol?
ii. Dihydric alcohols are those containing two hydroxyl groups per molecule. They are
also named glycols or diols.

Example 6.3

H2C CH2
OH OH
Ethane-1,2-diol (Ethylene glycol)

Can you give more examples of dihydric alcohols?

iii. Trihydric alcohols are those containing three hydroxyl groups in their molecular
structure.

Example 6.4
H2C CH CH2
OH OH OH
Propane-1,2,3-triol (Glycerine or glycerol)

iv. Polyhydric alcohols are those alcohols containing three or more hydroxyl groups
in their molecular structure.

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Can you give examples of polyhydric alcohols?

Classification of Monohydric Alcohols
Monohydric alcohols may be further classified according to the carbon atom to which
the hydroxyl group is attached.
Primary alcohols
In a primary alcohol, the carbon with the hydroxyl group is only attached to one alkyl
group.
H

General structure:
R C OH

H
Primary (1o) alcohol

Example 6.5
CH3
CH3-CH2-OH CH3-CH2-CH2-OH CH3-CH2-CH-CH2-OH
Ethanol 1-Propanol 2-Methyl-1-butanol

Secondary alcohols
In a secondary alcohol, the carbon with the hydroxyl group is attached to two alkyl
groups.

OH

General structure: R C R' Where, R and R' may be the same or dif f erent

Secondary (2o) alcohol

Example 6.6
OH OH OH

CH3-CH-CH3 CH3-CH2-CH-CH3 CH3-CH2-CH-CH2-CH3

2-Propanol 2-Butanol 3-Pentanol

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 CHEMISTRY GRADE 11

Tertiary alcohols
In a tertiary alcohol, the carbon with the hydroxyl group is attached to three other alkyl
groups.
OH

General structure: R C R' Where, R, R' and R'' may be the same or dif f erent

R''

Tertiary (3o) alcohol

Example 6.7
OH OH
CH3 C CH3 CH3CH2 C CH3
CH3 CH3
2-Methyl-2-propanol 2-Methyl-2-butanol

 
The common name of an alcohol is derived from the common name of the alkyl
group and adding the word alcohol to it. In the IUPAC system, an alcohol is named by
replacing the e of the corresponding alkane name with ol.

Example 6.8

CH3 H CH3 OH CH3 CH2 H CH3 CH2 OH

Methane Methanol Ethane Ethanol
(methyl alcohol) (ethyl alcohol)

When an alcohol consists of a chain with three or more carbon atoms, the chain is
numbered to give the position for the –OH group and any substituents on the chain.
For this, the longest carbon chain (parent chain) is numbered starting at the end nearest
to the hydroxyl group. The positions of the –OH group and other substituents are
indicated by using the numbers of carbon atoms to which these are attached.

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Example 6.9
OH

CH3 CH2 CH2 OH CH3 CH CH3

3 2 1 3 2 1
1-Propanol 2-Propanol
(propyl alcohol) (isopropyl alcohol)
Is neopentyl alcohol a 1°, 2°, or 3° alcohol?
For naming polyhydric alcohols, the ‘e’ of alkane is retained and the ending ‘ol’ is
added. The number of –OH groups is indicated by adding the multiplicative prefix, di,
tri, etc., before ‘ol’.

Example 6.10
OH
HO CH2 CH2 OH HO CH2 CH CH2 OH
2 1 3 2 1
1,2-Ethanediol 1,2,3-Propanetriol
(ethylene glycol) (glycerol)

Exercise 6.1
1. Give the general formula for the homologous series of monohydric
alcohols.
2. Classify the following alcohols as monohydric, dihydric and trihydric
alcohols.
a. 2-propanol b. 1,3-propanediol c. 1,2,3-butanetriol
3. Classify the following monohydric alcohols as primary, secondary or
tertiary alcohols.
a. 1-pentanol b. 2-pentanol c. 2-methyl-2-butanol
4. Give the IUPAC name for the following alcohols:
a. OH b. HO OH c. OH

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 CHEMISTRY GRADE 11

   

Activity 6.2
Answer the following questions in groups, and share your answers with the
whole class.
1. Is the bond in −O−H polar or non-polar? Why?
2. Compare the physical state of the first four members of monohydric
alcohols and alkanes.
3. Lower alcohols, like methanol and ethanol, are miscible with water in all
proportions, while lower hydrocarbons are not so. Explain.

The hydroxyl group in an alcohol is polar due to the high electronegativity of oxygen.
As a result, there is significant hydrogen bonding in alcohols (Figure 6.1).

δ δ R
δ H O
H δ δ δ δ δ
O H O H O
R R
Hydrogen R
bonding
       

Due to the hydrogen bonding in alcohols, they have higher melting and boiling
points than hydrocarbons of comparable molecular size (mass). Table 6.1 gives some
physical constants of the first six monohydric alcohols. Hydrogen bonding is also the
cause for even lower members to be liquids at room temperature.

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Group Assignment 6.1

Form a group of five and explain the following facts by
searching information from the internet and any other sources.
Submit your report inWord and PDF formats.
1. Dihydric and the trihydric alcohols have higher boiling
points than monohydric alcohols of similar molecular size
(mass).
2. The solubility of alcohols in water decreases with
increasing carbon number.
3. The water solubilities of dihydric and trihydric alcohols
are higher than those of monohydric alcohols of similar
molecular mass.
4. The boiling point of a branched isomer is lower than that
of its isomeric straight-chain alcohol.
Table 6.1: IUPAC Names, Condensed Structure and Physical Constants of the
First Six Monohydric Alcohol
Structure of monohy- IUPAC name Melting Boiling Density
dric alcohol point (°C) point (°C) (g/mL)
CH3OH Methanol −97 64.7 0.792
CH3CH2OH Ethanol −117 78.3 0.789
CH3CH2CH2OH 1-Propanol −126 97.2 0.804
CH3(CH2)2CH2OH 1-Butanol −90 117.7 0.810
CH3(CH2)3CH2OH 1-Pentanol −78.5 138 0.817
CH3(CH2)4CH2OH 1-Hexanol −52 156.5 0.819

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 CHEMISTRY GRADE 11

  

The general laboratory methods of preparation of alcohols are:

A. Acid-catalyzed hydration of alkenes:
Water is added to the double bond of an alkene in the presence of dilute acid
such as H2SO4 or H3PO4.
General Reaction:
H3O+
C C + HOH C C
H OH
Alkene Alcohol

Example 6.11

CH3
H3C H3O+
C CH2 + HOH H3C C CH2 H
25 °C
H3C
OH
2-Methylpropene
(isobutylene) tert-Butyl alcohol

Note that hydrogen of the water goes to the carbon of the alkene that contains more
hydrogens.
Does addition reaction change the hybridization of the carbon items initially held by
the double bond? Explain.

B. Hydrolysis of alkyl halides:

Warming alkyl halides with sodium hydroxide forms alcohols.
What does hydrolysis mean?
General Reaction:
R CH2X heat R CH2OH + NaX
+ NaOH
(X = Cl, Br, I) Alcohol
Alkyl halide

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 Alcohols and Ethers

Example 6.12

CH3 CH2Cl + heat NaCl

NaOH CH3 CH2OH +
Ethyl chloride Ethanol

C. Hydrolysis of Esters:
Heating esters with potassium hydroxide produces alcohols.
General reaction:
RCOOR' + KOH heat RCOOK + R'OH
Ester Alcohol

Example 6.13
heat
CH3COOCH2CH3 + KOH CH3COOK + CH3CH2OH
Ethyl acetate Ethanol

Methods B and C involve the replacement of other groups by the –OH group. Hence,
they are examples of substitution reactions.

Ethanol (Ethyl Alcohol), CH3CH2OH

Activity 6.3
Answer the following questions individually and share your answers with
others in the class.
1. Why is the shelf-life of some alcoholic beverages low, while for others it
is high?
2. How can you improve the shelf-life of those alcoholic beverages with a
low shelf-life?

Ethanol is the second member of the homologous series of monohydric alcohols.

It is one of the constituents of all alcoholic beverages. ‘Tella’, ‘Tej’, Beer, Wine,
‘Katikalla’, Ouzo, Gin and Whisky contain ethanol. There are a number of methods
for preparing ethanol using different materials.
Can you categorize the alcoholic beverages as distilled and non-distilled?

UNIT 6 275
 CHEMISTRY GRADE 11

Industrial preparation of ethanol

Ethanol is manufactured industrially by:
1. Fermentation of carbohydrates such as sugar. Fermentation is the slow
decomposition of carbohydrates such as sucrose, starch and cellulose in the
presence of a suitable enzyme. It results in the formation of ethanol and carbon
dioxide:

C12H22O11 + invertase C6H12O6 + C6H12O6

H2O
Sucrose Glucose Fructose

C6H12O6 2CH3CH2OH + 2CO2

Glucose Ethanol

Fermentation can produce an alcoholic beverage whose ethanol content is 12–

15% only. Why is it that difficult to produce a higher percentage of alcohols by
fermentation? How can a higher ethanol-containing beverage be produced?
Most liquor factories in Ethiopia use molasses, a by-product of sugar industries,
as a raw material to produce ethanol. In the brewing industry, germinated barley
called malt is used as the starting material. The whole process taking place in
breweries is summarized as follows:

2(C6H10O5)n + nH2O Diastase nC12H22O11 nH2O 2nC6H12O6

Starch Maltose Maltase Glucose

Zymase
C6H12O6 2CH3CH2OH + 2CO2
Glucose Ethanol

2. Catalytic Hydration of Ethene: Most ethanol is manufactured at present by this

method. In this process, ethene is treated with steam at 573 °K and 60 atm pressures
in the presence of phosphoric acid, H3PO4, catalyst.

H3PO4
CH2 CH2 (g) + H2O (g) CH3CH2OH (g)
Ethene 573 K/60 atm Ethanol

276 UNIT 6
 Alcohols and Ethers

Experiment 6.1
Preparation of Ethanol by Fermentation
Objective: To prepare ethanol from sugar.
Materials and chemicals: Conical flask, glass rod, distillation flask, condenser,
spatula, thermometer, watch glass, Bunsen burner, tripod, boiling chips, beaker,
stopper and delivery tube. Sugar, ammonium phosphate or ammonium sulphate,
yeast, Ca(OH)2.
Procedure:
1. Take 50 mL of distilled water in a conical flask, add 15 g of sugar to it and
stir. Add about 1 gram of yeast and a small amount of ammonium phosphate
or ammonium sulphate to the solution. Arrange the setup, as shown in 
 and let the flask stand for three days at a warm place.

     
Observations and analysis:
A. What is the purpose of adding yeast to the solution?
B. Why do we add ammonium phosphate or ammonium sulphate to the sugar
solution?
C. What happened to the calcium hydroxide solution at the end of the first or
second day? Which gas is produced?
D. What is the smell of the solution in the flask after three days?
E. What has happened in the flask containing the sugar solution as it stood for
three days?

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 CHEMISTRY GRADE 11

F. After three days, filter the solution, and arrange the set up as in 
Pour 20 mL of the filtrate in a distilling flask, with a few boiling chips, heat
the solution, and collect the liquid in a receiver.

     

Points to observe:
A. Observe the colour and identify the smell of the distillate.
B. Pour a small amount of the distillate on a watch glass, strike a match and
bring the flame close to the distillate. Does it catch fire?
C. Write a complete laboratory report on this experiment and submit it to your
teacher.

278 UNIT 6
 Alcohols and Ethers

Project 6.1
Form a group of five and do the following activities. Submit Word and PDF
documents to your teacher.
1. Search the preparation of “Katikalla”, “Tela”, “Tej”, and other locally
prepared alcoholic beverages in your community by interviewing
elders. Report your findings to the whole class.
2. Choose one locally prepared non-distilled alcoholic beverage in your
community and illustrate its preparation.
3. Compare the traditional and industrial methods of preparing alcoholic
beverages.
4. Search the internet or any other sources to summarize the properties
and uses of ethanol.

    

Activity 6.4
Discuss the following questions in groups, and write a report. Present
your report to the class.
1. Why do alcoholic beverages such as “Tela”, “Tej”, beer and wine turn
sour if they are not properly stored? Which reaction of alcohols is
responsible for this? Write a chemical equation to support your answer.
2. What types of reactions do alcohols undergo? Alcohols contain
a hydrocarbon group and a functional group (–OH). Which part
of alcohols is responsible for most of their chemical reactions?

Reactions of alcohols may involve the cleavage of the oxygen–hydrogen bond

(– O–H) or the carbon-oxygen bond (–C–O).

1. Reactions of alcohols involving cleavage of –O–H bond

a. Reaction with Active Metals
Alcohols react with Li, Na, K, Mg, and other active metals to liberate hydrogen and
to form metal alkoxides.

UNIT 6 279
 CHEMISTRY GRADE 11

General reaction:
2 R CH2 O H + 2 Na 2 R CH2 O Na + H2
Alcohol Sodium alkoxide

Example 6.14
-
2 CH3 CH2 O H + 2 Na 2 CH3 CH2 O Na
+ + H2
Ethanol Sodium ethoxide

Experiment 6.2
Reactions of Alcohols with Active Metals
Objective: To observe the reaction of alcohols with sodium and magnesium.
Materials required: Ethanol, sodium and magnesium metal. Test tubes, test
tube holder, test tube rack, measuring cylinder, Bunsen burner, scissors or knife.
Procedure:
Take two test tubes and add 2-5 mL of ethanol to each of the test tubes. Cut a
very small piece of sodium with a knife and drop it into the first test tube. Take
magnesium ribbon and drop it in the second test tube.
Observations and analysis:
A. What do you observe
a. in the first test tube? b. in the second test tube?
B. Is there an evolution of gas? How do you check this gas is hydrogen?
C. If no reaction occurs in any of the test tubes, heat the mixture gently using a
Bunsen burner and write your observation.
D. Which bond of the alcohol is broken in the reaction?
E. Write a general reaction for such reactions.
F. What type of metals reacts in this manner?

b. Oxidation of alcohols
The oxidation products of alcohols depend on the type of alcohol and the nature of
oxidizing agents. Oxidation of alcohols is a very important method for the production
of other oxygen-containing organic compounds, such as aldehydes, ketones and
carboxylic acids.

280 UNIT 6
 Alcohols and Ethers

i. Oxidation of primary alcohols

Depending on the oxidizing agent used, a primary alcohol is oxidized to an aldehyde
which in turn is oxidized to a carboxylic acid in the presence of mild oxidizing
agents such as copper metal, primary alcohols yield aldehydes.
General reaction:
O
Cu
R CH2 OH R C H
Primary alcohol 360 °C Aldehyde

Example 6.15
O
Cu
CH3 CH2 OH CH3 C H
Ethanol 360 °C Ethanal

Strong oxidizing agents, such as acidified KMnO4 or K2Cr2O7 or CrO3 in H2SO4,

oxidize primary alcohol first to aldehydes and then to carboxylic acids. It is difficult to
stop the reaction at the aldehyde stage.
General reaction:
O O
KMnO4/ H KMnO4/ H
R CH2 OH R C H R C OH
Primary alcohol Aldehyde Carboxylic acid

Example 6.16
O O
KMnO4/ H KMnO4/ H
CH3 CH2 OH CH3 C H CH3 C OH
Ethanol Ethanal Ethanoic acid

Is there any possibility to prepare aldehydes from primary alcohols?

ii. Oxidation of secondary alcohols yields ketones
General reaction:
OH O
[O]
R C R' R C R'
H
Secondary alcohol Ketone

UNIT 6 281
 CHEMISTRY GRADE 11

Example 6.17

OH O
+
KMnO4/H
H3C C H H3C C CH3

CH3 Propanol
2-Propanol (acetone)

iii. Tertiary alcohols and ketones are generally resistant to oxidation

OH
[O]
R C R' No reaction
under normal conditions
R''

Tertiary alcohol

What happens if 3° alcohols subject to oxidation under drastic conditions?

Group Assignment 6.2

Do the following activity in a group of five and share your
responses with the whole class.
Alcohols A, B, and C all have the composition C4H10O.
Molecules of alcohol A contain a branched carbon chain
and can be oxidized to an aldehyde; molecules of alcohol B
contain a linear carbon chain and can be oxidized to a ketone;
and molecules of alcohol C can be oxidized to neither an
aldehyde nor a ketone. Predict the structural formulas of
these molecules.

2. Reactions involving cleavage of carbon–oxygen (C – O) bond in alcohols

a. Dehydration of alcohols: Alcohols undergo dehydration (removal of a molecule
of water) to form alkenes on treating with an acid such as concentrated H2SO4 or
H3PO4 and heating.

282 UNIT 6
 Alcohols and Ethers

General reaction:
H H
Conc.H2SO4 R H
R C C OH C C + H2O
∆ H H
H H
Alcohol Alkene

In general, dehydration of primary alcohols is difficult and requires concentrated acid

and high temperature.

Example 6. 18
Ethanol dehydrates in the presence of concentrated H2SO4 and heating at 170 °C.
H H
Conc.H2SO4 H H
H C C OH C C + H2O
170 °C H H
H H
Ethanol Ethene

Secondary and tertiary alcohols dehydrate under milder conditions.

Example 6.19
OH
85% H3PO4
CH3 CH CH3 CH3 CH CH2 + H2O
167 °C
2-Propanol Propene

CH3 CH2
20% H3PO4
CH3 C OH CH3 C CH3 + H2O
85 °C
CH3
2-Methyl-2-propanol 2-Methylpropene

Arrange primary, secondary, and tertiary alcohols in the degree of dehydration order.
b. Reactions of alcohols with hydrogen halides: Alcohols react with hydrogen halides
to form alkyl halides.

UNIT 6 283
 CHEMISTRY GRADE 11

General reaction:
R CH2 OH + HX R CH2 X + H2O
Alcohol (X = Cl, Br, I)
Alkyl halide

Example 6.20

CH3 CH2 OH + HBr CH3 CH2 Br + H2O

Ethanol Ethyl bromide
(1-bromoethane)

Is it possible to produce alcohols from alkyl halides?

Exercise 6.2
1. What is the functional group in alcohols?
2. Classify the following alcohols as primary, secondary and tertiary
alcohols:
a. 3-hexanol b. 2-methyl-2-pentanol c. 3-methyl-2-butanol
d. 1-heptanol e. 2-methyl-1-propanol f. 2,3-dimethyl-2-butanol
3. Compare boiling points of alcohols and hydrocarbons of similar
molecular mass. Explain if there is any difference.
4. Complete the following chemical reactions in your exercise book:
CrO3/H2SO4
a. CH3CH2CH2CH2OH
OH
b. H3C CH2 K2Cr2O7/ H
CH CH2CH3

284 UNIT 6
 Alcohols and Ethers

   

Activity 6.5
Try to answer the following questions in groups, and present your
responses to the whole class.
1. Diethyl ether (CH 3CH 2-O-CH 2CH 3) is prepared from ethyl alcohol
(CH 3CH 2-OH). Based on these information and your prior knowledge of
molecular structures, discuss these questions.
a. From CH 3CH 2-OH and CH 3CH 2-O-CH 2CH 3, which one do you
expect to have higher boiling point?
b. Which one of these compounds is more soluble in water? Why?
Ethers are compounds in which an oxygen is bonded to two alkyl substituents (R−
O−R’), where R and R’ may be the same or different. If the alkyl substituents are
identical, the ether is a symmetrical ether. If the substituents are different, the ether is
an unsymmetrical ether.
R −O−R R − O − R'
a symmetrical ether an unsymmetrical ether
The common name of an ether consists of the names of the two alkyl substituents
(in alphabetical order), followed by the word “ether”. The smallest ethers are almost
always named by their common names.

Example: 6.21

CH3
a. CH3 O CH2CH3 b. CH3CH2 O CH2CH3 c. CH3CH O CH2CH3
ethylmethyl ether diethyl ether ethylisopropyl ether

The IUPAC system names ether as an alkane with an RO− substituent. The substituents
are named by replacing the “yl” ending in the name of the alkyl substituent with “oxy”.

CH3O CH3CH2O CH3CHO

methoxy ethoxy CH3

isopropoxy

UNIT 6 285
 CHEMISTRY GRADE 11

Example 6.22

OCH3
a. CH3CHCH2CH3 b. CH3CH2CH2CH2CH2 OCH2CH3
2-methoxybutane 1-ethoxypentane

Exercise 6.3
1. Give the systematic (IUPAC) name for each of the following ethers:

a. CH3CH2CH2OCH2CH2CH2CH3 b. CH3CH2CH2CH2CHCH2CH3
OCH3

2. What are the common names of the compounds given in question 1?

   

Ethers are polar compounds in which oxygen bears a partial negative charge and each
carbon bonded to it bears a partial positive charge (Figure 6.4).
How do ethers differ from alcohols?
The boiling points of ethers are much lower than those of alcohols of comparable
molecular weight. For example, the boiling points of ethanol (78 °C) is much higher
than its constitutional isomer dimethyl ether (-24 °C). The difference in boiling points
between these two compounds is due to the polar O−H group in the alcohol, which
is capable of forming intermolecular hydrogen bonds. How do you rate the boiling
points of ethers and hydrocarbons of comparable molecular weight?
only very weak
dipole-dipole interaction
H
H H
δ H C
H O δ
C C Oδ
δ δ
Cδ H
H H
H H
H H
             
  

286 UNIT 6
 Alcohols and Ethers

Because the oxygen atom of ether carries a partial negative charge, ethers form
hydrogen bonds with water (Figure 6.5) and are more soluble in water than are
hydrocarbons of comparable molecular weight and shape.
H
H
δ C H
δ O δ
δ
H H Oδ
Cδ H

hydrogen bonding H H

      

Exercise 6.4
1. Arrange these compounds in order of increasing solubility in water:
a. CH 3OCH 2CH 2OCH 3 b. CH 3CH 2OCH 2CH 3
c. CH 3CH 2CH 2CH 2CH 2CH 3
2. Arrange these compounds in order of increasing boiling point:
a. CH 3OCH 2CH 2OCH 3 b. HOCH 2CH 2OH c. CH 3OCH 2CH 2OH
3. Write the condensed structures of both isomers with the formula C2H 6O.
Label the functional group of each isomer.

 

1. Dehydration of alcohols
Alcohol undergoes dehydration in the presence of protic acids (sulphuric acid,
phosphoric acid) to produce alkenes and ethers under different conditions. For
example, ethanol is dehydrated to ethene at 170 °C in the presence of sulphuric
acid. On the other hand, ethanol yields ethoxyethane in the presence of sulphuric
acid at 140 °C. The method is limited to use with primary alcohols.
H2SO4
CH3CH2OH CH2 CH2 + H2O
ο
Ethanol 170 C water
Ethene
H2SO4
2CH3CH2OH CH3CH2OCH2CH3 + H2O
Ethanol 140 οC Diethyl ether water

UNIT 6 287
 CHEMISTRY GRADE 11

What is the problem if we use secondary and tertiary alcohols? Does this method work
for the synthesis of both symmetrical and unsymmetrical ethers?
2. Williamson ether synthesis
In this method, an alkyl halide is made to react with an alkoxide which leads to
the formation of ether.

R X + R O R O R + X
Alkyl halide Alkoxide ion Ether

Can this method be used for the preparation of both symmetrical and unsymmetrical
ethers?

Example 6.23

CH3CH2Br + CH3O CH3CH2OCH3 + Br

ethyl bromide methoxide ion ethyl methyl ether

CH3CH2CH2CH2I + CH3CH2O CH3CH2CH2CH2OCH2CH3 + I

butyl iodide ethoxide ion butyl ethyl ether

 
Ethers, R−O−R, resemble hydrocarbons in their resistance to chemical reaction. They
do not react with oxidizing agents, such as K2Cr2O7 or KMnO4. Ethers are not affected
by bases, however, they can react with proton donors to form oxonium salts.

Example 6.24

CH3CH2OCH2CH3 + HBr CH2CH3 O CH2CH3 Br

H
An oxonium salt

Heating dialkyl ethers with very strong acids (HI, HBr, and H2SO4) cleaves the ether
linkage:
∆
CH3CH2OCH2CH3 + 2 HBr 2 CH3CH2Br + H2O

288 UNIT 6
 Aldehydes and Ketones

Ethers are not affected by most reagents at moderate temperatures. Because of their
good solvent properties and general inertness to chemical reaction, ethers are excellent
solvents in which to carry out many organic reactions.

Exercise 6.5
1. What are the common uses of ethers in medicine and industry?
2. Outline how the alkoxide ion is prepared for the Williamson ether
synthesis using a chemical equation.

6.3 

At the end of this section, you will be able to:

) write the general structural formulas of aldehydes and ketones
) give the structures and names of common members of each group
) describe the physical properties of aldehydes and ketones
) explain some methods of preparation of aldehydes and ketones
) explain the chemical reactions of aldehydes and ketones such as addition,
oxidation and reduction
) give some chemical tests that differentiate aldehydes from ketones.

Activity 6.6
Answer the following questions in groups then present your response to
the whole class.
1. What functional group form if one of the carbon in the C=C is
replaced by an oxygen atom?
2. What is the common type of reaction for alkenes?
3. Which type of reaction do you expect for aldehydes and ketones?

The functional group of an aldehyde is a carbonyl group (C=O) bonded to a hydrogen

atom. In methanal (formaldehyde), the carbonyl group is bonded to two hydrogen
atoms. In other aldehydes, it is bonded to one hydrogen atom and one carbon atom.
The functional group of a ketone is a carbonyl group bonded to two carbon atoms.

UNIT 6 289