1

2016/2024 BY: GARAMU NAMARA( MSc)

 INTRODUCTION
2
 Organic compound
3

 The history of organic cpds started from the synthesis of urea in the
lab from NH4CNO by Friedrich Wöhler

 The branch of chemistry that studies organic cpds (carbon cpds ) is

called organic chemistry

 Catenation is the ability of atoms of the same element to join

together forming short or long chains & rings

 The organic compounds that are synthesized by living organisms are

called natural products
 Based on their functional group, organic cpds are classified as
alkanes, alkenes, alkynes, aromatics, alcohols, aldehydes, ketones,
carboxylic acids, esters & ethers
4

 Functional group - part of a molecule or a cpd that determines

the chemical & physical properties of that molecule or cpd
 The functional group of an alkene, for example, is its
carbon-carbon double bond
 Hydrocarbons are class of organic cpds composed of the
carbon & hydrogen atoms only
 alkanes, alkenes, alkynes & aromatics are hydrocarbons
 Organic compound
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6
 Oxygen containing organic compound
7
 Classification of organic compounds
8

Organic Class of
General Molecular Formula
Compounds
Alkane CnH2n + 2
Alkene CnH2n
Alkyne CnH2n − 2
Alcohol CnH2n+1OH
Ether CnH2n+2+1O
Aldehyde CnH2nO
Ketone CnH2nO
Carboxylic acids CnH2n+1CO2H
Esters CnH2n+CO2
 Oxygen containing hydrocarbons
9

 In this presentation we will introduce the major

organic compound that contain oxygen.
This includes:
Alcohols Ethers
Phenols Esters
Carboxylic Aldehyde
acids ketones
10

 Functional group
 Some important oxygen containing
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organic compound
 Are also called hydrocarbon derivatives or

 Includes: alcohols, ethers, aldehydes, ketones,

carboxylic acid and esters
12

Most people think of two common alcohols:

 thesubstance that intoxicates people, and
 The one used in clinics and hospitals.

 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more of the hydrogen atoms in the hydrocarbon have been
replaced by a hydroxyl group (–OH).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.
 In alcohols, the hydroxyl group is directly attached to
carbon atom(s) of an aliphatic system.
 Alcohols…
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14
 Classification of alcohols
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16
 Classification of alcohols
17

Monohydric alcohols are alcohols containing only one

hydroxyl group
CH3 CH2 OH
Ethanol
CH3 CH2 CH2OH
1-Propanol
CH3 CH2 CH2CH2OH
1-Butanol (Butan-1-ol)
 Classification of alcohols
18

Dihydric alcohols:
 are those containing two hydroxyl groups per molecule.
 They are also named glycols or diols.

Ethane-1,2-diol (Ethylene glycol)

 Poly hydroxy alcohol…
19

Trihydric alcohols:
 are those containing three hydroxyl groups in
their molecular structure

Propane-1,2,3-triol(Glycerine or glycerol)
 Poly hydroxyl alcohol
20

 Polyhydric alcohols are those alcohols

containing three or more hydroxyl groups
in their molecular structure.
 activities
21

Classify the following alcohols as monohydric,

dihydric and trihydric alcohols.
a. 2-propanol
b. 1,3-propanediol
c. 1,2,3-butanetriol
22

 There are four possible bonding patterns for alkyl

carbons in hydrocarbons.
are carbons attached to one other
carbon and three hydrogen's. Also known as a methyl
(CH3)
are attached to two other
carbons and two hydrogens. Also known as methylene
(CH2) carbons.
are attached to three other carbons
and one hydrogen. Also known as methine (R3CH) carbons
are attached to four other
carbons.
 Types of alkyl carbon in alkyl
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hydrocarbon
24

Monohydric alcohols may be further classified according to

the carbon atom to which the hydroxyl group is attached
: In a primary alcohol, the carbon with the
hydroxyl group is only attached to one alkyl group
General structure:

Example:
25

In a secondary alcohol, the

carbon with the hydroxyl group is attached to two
alkyl groups.
Where, R and R' may
General be the same or different
structure: Secondary (2o) alcohol
Example :
26

Tertiary alcohols: In a tertiary alcohol, the carbon with

the hydroxyl group is attached to three other alkyl
groups.
Where, R, R' and R'' may be
the same or different
General
structure:
Tertiary (3o) alcohol
Example:
27
28

Classify the following monohydric alcohols as

primary, secondary or tertiary alcohols.
a. 1-pentanol
b. 2-pentanol
c. 2-methyl-2-butanol
d. Ethylalcohol
e. Isopropyl alcohol
f. tert-butyl alcohol
 Nomenclature of Alcohols
29

systems for the nomenclature of Monohydric Alcohol.

Common System:
 Alcohols with one to four carbon atoms are frequently called
by common names,
 In this system, we name the monohydric alcohols as Alkyl
Alcohol.
 We get their names by adding the name alcohol after the
name of the alkyl group present in the molecule.
Example: The compound CH3-OH has one methyl group with an
alcohol group. Hence, we call it Methyl Alcohol.
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31

Table : Classification and Nomenclature of Some Alcohols

Condensed Structural
Class of Alcohol Common Name IUPAC Name
Formula

CH3OH — methyl alcohol methanol

CH3CH2OH primary ethyl alcohol ethanol
CH3CH2CH2OH primary propyl alcohol 1-propanol

(CH3)2CHOH secondary isopropyl alcohol 2-propanol

CH3CH2CH2CH2OH primary butyl alcohol 1-butanol

CH3CH2CHOHCH3 secondary sec-butyl alcohol 2-butanol

(CH3)2CHCH2OH primary isobutyl alcohol 2-methyl-1-propanol

(CH3)3COH tertiary tert-butyl alcohol 2-methyl-2-propanol

secondary cyclohexyl alcohol cyclohexanol

 IUPAC System:
32

 In IUPAC nomenclature, we term the alcohols as

Alkanols.
 We get the name of any alcohol by replacing the last
‗e‘ from the name of the corresponding alkane by the
suffix ‗–ol‘.
33

When an alcohol consists of a chain with three or more carbon

atoms the following rule is applied
The rules are summarized in a three-step procedure:

2. Number the longest carbon chain starting at the end nearest

the ―OH group, and use the appropriate number, if
necessary, to indicate the position of the ―OH group.
34

4. Combine the name and location for other groups, the

hydroxyl group location, and the longest chain into the
final name.
5. If there are more than one –OH group do not remove
the –e from the suffix, but add a di- or tri- prefix to the –
ol suffix.
6. Identify and locate the other branches on the chain so
that they are named alphabetically and their carbon
number is hyphenated onto the front of the name.
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37
38

 When naming a cyclic alcohol, start numbering the

ring beginning with the carbon connected to the OH group. This
rule always puts the OH group at C1therefore, the ―1‖ is usually
omitted from the name:

 When other groups are present on the ring, it is numbered

clockwise or counterclockwise depending on which direction
gives the next substituent the lower number:
39
 Polyhydric alcohol
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 Suffixes like ―diol‖ and ―triol‖ are used when there

are many -OH groups present in a single molecule
(polyhydroxy alcohols).
 When naming polyhydroxy alcohols, the parent
alkane‘s final ‗-e‘ is maintained (retained).
Example:
 Nomenclature of diols
41

Two OH
42

common name

)
 phenols
43
 phenols
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 Naming of alkenols
45
 Alcohols and carboxylic acid
46
 Priority in naming
47
 Physical properties of alcohols…
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 Explain the physical properties of alcohols

 explain the chemical reactions of alcohols
such as oxidation, reaction with active
metals,esterification and dehydration
 Physical properties of alcohols
49

 The physical and chemical properties of alcohols are

mainly due to the presence of hydroxyl group.

ALCOHOLS:
HAS TWO PARTS

• Alkyl group
• Hydrophobic: water fear
or hate
• Non polar

- • Functional group(hydroxyl
group
• Hydrophilic: water loving
• Polar
 Physical properties of alcohols…
50

: lower alcohols are colorless liquid at

room temperature
 Higher molecular weight alcohols are solid at room
temperature
 They have characteristic sweet smell

Melting and boiling point of alcohols much higher than

corresponding alkanes.
 Physical properties of alcohols
51

 Inter molecular hydrogen bonding in alcohols

Hydrogen
bonding
 Physical properties of alcohols…
52

 Melting and boiling point of alcohols generally increase

with the size of alkyl groups(number of carbon)
Melting Boiling
Structure of monohy Density
IUPAC name point point
dric alcohol (g/mL)
(°C) (°C)
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
 Physical and chemical properties of
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alcohols…

 Boiling point increase with number of carbon

 Physical properties of alcohols…
54

2.
The melting point and boiling point increase with
number of hydroxyl(-OH) groups
 i.e Dihydric and the trihydric alcohols have higher boiling
points than monohydric alcohols of similar molecular size
(mass).
Boiling points
London forces
Ethane: -89oC
London + H-bonding
Methanol: 65oC
London + H-bonding
Ethanol: 78oC
1,2-Ethane diol: 197oC London + more
H-bonding
1,2,3propane triol:290oC
 Physical properties of alcohols…
55

 Straight chain alcohols have higher boiling point than

branched chain
Example:
n-butyl alcohol
CH3CH2CH2CH2OH, boils at 117.7°C, while
tert butyl alcohol

boils at 82.5°C
 Physical properties of alcohol…
56

Lower member of alcohols are completely soluble in

water.
i.eThe first three alcohols, methanol, ethanol and 1-
propanol are miscible with water in all proportions
 Solubility of higher alcohols in water decreases due to
increase in size non polar alkyl group.
 The water solubility of dihydric and trihydric alcohols
are higher than those of monohydric alcohols of similar
molecular mass. because they have more opportunities
for hydrogen-bonding with water
 Physical and chemical properties of alcohols…
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Solubility of alcohols in graph:

 Solubility decrease as number of alkyl carbon increase
 Physical properties of alcohols
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summary
 Home work
59

1. Why boiling point of alcohols is higher than that of

alkanes of corresponding molecular weight?
2. Arrange the compounds in order of increasing solubility
in water (least first)

3. Arrange the three types of monohydric alcohols(n-

butyl alcohol, isobutyl alcohol and tert butyl alcohol) in
increasing order of :
A. Solubility
B. Boiling And Melting Point
 Preparation of alcohols
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 List and explain general methods of preparation

of alcohols

:
 Preparation of alcohols
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The general laboratory methods of preparation of alcohols are:

 Water is added to the double bond of an alkene in the presence

of dilute acid such as H2SO4 or H3PO4
 In case of unsymmetrical alkenes, the addition reaction takes
place in accordance with
General Reaction:
 Preparation of alcohol: hydration of
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alkenes…

example
 Preparation of alcohols…
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 Warming alkyl halides with sodium hydroxide forms

alcohols.
Is substitution reaction
 Preparation of alcohols…..
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 C. Hydrolysis of Esters: is substitution reaction

 involve the replacement of other groups by the –OH
group.

Heating esters with potassium hydroxide produces

alcohols.
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Predict the product for each acid-catalyzed hydration of

the alkene reaction.
 Home work
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 The major product obtained in the reaction

a.

H+
B.
67

Ethanol (Ethyl Alcohol), CH3CH2OH

 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.
68

1.
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:
69

 Fermentation can produce an alcoholic beverage whose ethanol

content is 12–15% only. Why?
 The alcohol kills the yeast and inhibits its activity when the
percentage is higher.
 To produce beverages of higher ethanol content, distillation of
the aqueous solution is required

 Most liquor factories in Ethiopia use molasses.

a by-product of sugar industries.
70

 In the brewing industry called

malt is used as the starting material.
summarized as follows
 Preparation of ethanol…
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2.
 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.
 Concept map of alcohol
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 Concept map of alcohols
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 Chemical properties of alcohols…
74

List and explain chemical reaction of alcohols such as

oxidation reaction, with active metals, and dehydration,
reaction of alcohol with hydrogen halide

 what types of reactions do alcohols undergo?

 Which part of alcohols is responsible for the chemical
reactions?
 Chemical properties of alcohols
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 The chemical and physical properties of the alcohols

are primarily dependent upon the
hydroxyl (OH) group, i.e. on the functional group of
the alcohol.
 Depending upon which bond is broken, the reactions
of alcohols are divided into two categories.
 i.e. it has two reactive covalent bonds, the C–O bond
and the O–H bond
76

1. Reactions with cleavage of O-H bond:

 Alcohols react with active metals such as sodium, potassium,

etc., to form alkoxides.
 The reaction is accompanied by the release of hydrogen gas.

e.g. 2CH3-CH2-OH + 2Na→2CH3–CH2-ONa + H2↑

77

b.
 is a very important method for the production of other
oxygen-containing organic compounds, such as
aldehydes, ketones and carboxylic acids.
 When alcohols oxidize, two bonds are broken, and
one new bond is formed. Oxidation of alcohols is
accompanied by:
1. Cleavage of O-H and C-H bonds
2. Formation of C=O bond
 The oxidation products of alcohols depend on the type
of alcohol and the nature of oxidizing agents.
 Reaction involve bond cleavage
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-O-H…

 Depending on the oxidizing agent used, a primary alcohol

is can be oxidized to: an aldehyde or carboxylic acid.

 in the presence of such as copper

metal, primary alcohols yield aldehydes
 Reaction involve bond cleavage
-O-H…
79

 in the presence of oxidizing agent such as acidified

KMnO4 or K2Cr2O7 or CrO3 in H2SO4 primary alcohol
oxidized to carboxylic acid. b/c It is difficult to stop
the reaction at the aldehyde stage.
 Reaction involve bond cleavage-O-H…
80

 Oxidation of secondary alcohols yields

ketones

N.B. Tertiary alcohols and ketones are

generally resistant to oxidation
81

Do the following activity and share your responses

Alcohols , , and all have the composition

. Molecules of alcohol contain a branched carbon
chain and can be oxidized to an aldehyde; molecules of
alcohol contain a linear carbon chain and can be oxidized to
a ketone; and molecules of alcohol can be oxidized to
neither an aldehyde nor a ketone. Predict the structural
formulas of these molecules.

Which of the following alcohols react

with acidified potasium permanganate
A. 2-methayl 1- propanol B. 2 methyl 2- prpopanol
C. 1 butanol D. 2 butanol
82

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

Example:
Ethanol dehydrates in the presence of concentrated H2SO4 and
heating at 170 °C
83

 Secondary and tertiary alcohols dehydrate

under milder conditions.
Example

The ease with which alcohols dehydrate is as follows:

84

b. Reactions of alcohols with hydrogen halides:

Alcohols react with hydrogen halides to form alkyl
halides.
 Do the following activity and share your responses
85

Alcohols , , and all have the composition

.
 Molecules of alcohol contain a branched carbon
chain and can be

 molecules of alcohol contain a linear carbon chain

and can be
 molecules of alcohol

a. Predict the structural formulas of these molecules

b. arrange these three molecules(A,B,C) in degree of
dehydration (the least first)
86

. The dehydration of alcohols is an example of

A) Elimination B) substitution reaction C) addition reaction
D) single displacement reaction
.Which one is the correct order of reactivity of
different types of alcohol towards hydrogen halide?
A) 1° alcohol > 2° alcohol > 3° alcohol
B) 2° alcohol > 1° alcohol > 3° alcohol
C) 3° alcohol > 1° alcohol > 2° alcohol
D) 3° alcohol > 2° alcohol > 1° alcohol
 ACTIVITIES
87

Why the ease of dehydration of alcohols

follows sequence, tertiary>secondary>primary?
A. Tertiary alcohol is most reactive of all while primary is the

least reactive
B. Because carbocation is the intermediate formed and their
stability order is also tertiary>secondary>primary.
C. Because tertiary alcohol is least stable followed by
secondary and then primary alcohol.
D. Tertiary alcohol reacts with acids faster followed by

secondary and then primary.

88

Ethers are compounds in which an oxygen is bonded to

two alkyl substituents
 where R and R‘ may be the same or different.

 Ethers are generally classified into two categories on

the basis of substituent groups attached:
when two identical groups are
attached to the oxygen atom.
: when two
different groups are attached to the oxygen atom.
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90

 The smallest ethers are almost always named by

their common names.
 The common name of an ether consists of the names
of the two alkyl substituents (in alphabetical order),
followed by the word ―ether‖
 If the two groups are the same, the prefix ―di-‖ is
used


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Rules
Select the longest carbon chain as the base
chain(root name) as the alkane
Change the name of the smaller alkyl group end
with yl in to oxy (—OR = alkoxy group) substituent on
this alkane.
 Example: Methyl (-CH3) (becomes methoxy (-OCH3)
and ethyl(-CH2CH3 ) becomes an ethoxy(-OCH2CH3
)group.
: Alkoxy name is placed with a locator number in
front of the base chain name.
 IUPAC NAME OF ETHER
92

E.g. CH3 O CH2CH3

ethyl methyl ether(common name)
methoxy ethane (IUPAC)

E.g.2 CH3CH2 O CH2CH2CH2CH3

butylethyl ether (common name)
1 ethoxy butane (IUPAC)
93
94

 Give the systematic (IUPAC) name for each of

the following ethers:
a. CH3CH2CH2OCH2CH2CH2CH3
95

 Dimethylether and ethyl methyl ether are gases at

ordinary temperature.
 The other lower homologes are colourless, pleasant
smelling, volatile liquids with typical ether smell.
The C - O bonds in ether are and
thus ethers have a .

 The boiling points of ether molecules are comparable to

that of alkanes. The weak polarity of ethers does
not appreciably affect their boiling points.
96

 Ethers have much lower boiling points as compared to isomeric

alcohols.
 This is because alcohols molecules are associated by
hydrogen bonds while ether molecules are not.
 example, the boiling points of ethanol (78°C) is much higher
than its constitutional isomer dimethyl ether (-24°C).

Ethers containing up to three carbon atoms are soluble

in water, due to their hydrogen bond formation with water molecules
 The solubility decreases with increase in the number of carbon atoms.
 The relative increase in the hydrocarbon portion of the molecule
decreases the tendency of Hydrogen bond formation.
 Physical properties of ether
97

 In ethers, the oxygen atom is sp3 hybridized with a

bond angle of 109.50.

 Ether is less polar than, alcohols because of the

oxygen atom that is unable to participate in hydrogen
bonding due to the presence of bulky alkyl groups on
both sides of the oxygen atom. but ether is more
polar than alkenes.
98

 There are different methods for the synthesis of ethers

some of which are being described as follow:
:
 the formation of reaction product, alkene or ether
depends on the reaction conditions.
 This method involves heating of excess of primary
alcohol with concentrated sulphuric acid and the
temperature has to be maintained around 4130 K
(140OC)to get symmetrical ether.
99

EXAMPLE:
 in the presence of sulphuric acid, dehydration of
ethanol at 443 K(1700C) yields ethene.
 On the other hand, it yields ethoxyethane at 413
K(1400C). This is an ideal method of preparation for
primary alcohols.
100

 Tertiary alkyl halides undergo elimination

reaction with sodium alkoxide to produce
alkenes.eg.

Therefore to prepare t- alkyl-alkyl ether, one

must take an alkyl halide with tertiary alkoxide.
Eg.

alkoxide ether
101

 Preparation of ethers by acid dehydration of

secondary or tertiary alcohols is .
Give reason.

In secondary and tertiary alcohols, the alkyl groups

create steric hindrance and the nucleophilic attack
becomes difficult. Hence, elimination to form alkene is
favored over substitution to form ether.
102

2. Williamson ether synthesis

 an alkyl halide is made to react with an alkoxide which
leads to the formation of ether or
 involves the treatment of an alkyl halide with sodium or
potassium salt of alcohol or phenol

N.B. this an important method for the preparation of

and ethers in laboratories.
103
 Reaction of ether
104

 Ethers, R-O-R, resemble hydrocarbons in their resistance

to chemical reaction.
 They do not react with oxidizing agents, such as

 Ethers are not affected by

 Reaction of ether
105

 Oxonium salt formation : When ethers are dissolved

in cold, strong mineral acids, such as sulfuric or
hydrochloric acid, they can act as weak Lewis bases
and produce oxonium salts.
106

 Heating dialkyl ethers with very strong acids (HI, HBr, and
H2SO4) cleaves the ether linkage:
 Cleavage takes place only under quite extreme
conditions, like in concentrated acids (usually HI or HBr)
and high temperatures.
A dialkyl ether produces:
 initially, an alkyl halide and an alcohol.

 R-O-R + HX → RX + R-OH
 This alcohol may react further and form a second mole of
alkyl halide
 RX + R-OH+HX⟶ 𝟐𝑹𝑿
 The order of reactivity is given as HI>HBr>HCl
 Reaction of ether…
107

example
 Reaction of ether…
108

Ethers may be used as solvents because they

react only with:
 Use of ethers
109

The common uses of ethers include:

 We use as a refrigerant and as a
solvent at low temperature.
is a common ingredient as an
anaesthesia in surgery.
is common as a solvent for oils, gums,
resins etc.
 We use as a heat transfer medium
because of its high boiling point.
 ALDEHYDE AND KETONES
110

What are Aldehydes?

 The carbonyl group (C=O) has one hydrogen atom

attached to it together with either a 2nd hydrogen atom

or a hydrogen group which may be an alkyl group or
one containing a benzene ring.
 The functional group of an aldehyde is a
carbonyl group (C=O) bonded to a hydrogen
atom
 Nomenclature of aldehyde
111

 Common name for aldehydes are obtained

from the names of the corresponding carboxyllic
acids.

Formal dehyde

acetaldehyde
 Naming of aldehyde
112

IUPAC names for aldehydes :

 are obtained by replacing the ending –e of the

corresponding alkane with –al-.

 Aldehyde functional group is always terminal in chain.

 When other substituents are present, the carbonyl

carbon is assigned number 1

 Naming of aldehyde
113

example
 Carbonyl compound
114

What are Ketones?

 In ketones, the carbonyl group has 2 hydrocarbon

groups attached to it. These can be either the ones

containing benzene rings or alkyl groups.
 The functional group of a ketone is a carbonyl group

bonded to two carbon atoms.

 Ketone does not have a hydrogen atom attached to

the carbonyl group.

butanone
115

 Common names of ketones are named on the basis of

the alkyl group attached to the carbonyl group
 Naming of ketones
116

 designated by suffix – one.

 Prefix is the name of hydrocarbon (Alkanones).
 The longest hydrocarbon chain containing carbonyl
carbon is selected and named it by substituting ‗e‘ of
Alkane with ‗one‘.
 While numbering the chain lowest number is given to
carbonyl carbon.
 Other substituents are numbered named and placed as
prefixes in alphabetic order.
 If there are two carbonyl groups in a molecule, it is
named as Alkanedione.
 Naming of ketones
117

example
 Naming of ketones
118
 IUPAC NAME OF KETONES
119

 E.g..
 IUPAC NAME OF KETONES
120

e.g.
 Physical properties of aldehyde
121

 In aldehyde the first member HCHO is gaseous at room

temperature.
 Acetaldehyde is liquid in nature with b.p. 200C.
 Lower aldehydes are colourless liquids.
 Benzaldehyde is liquid with characteristic smell of bitter
almonds.
 Lower members of aldehydes possess unpleasant smell
122

 Lower ketones are colourless liquids

 Lower ketones possess pleasant, sweet odours.
 Density of ketones is less than water
123

The boiling points of

which have
comparable molecular weights.
Carbonyl group compounds are
due to of partial negative
charge of carbonyl oxygen of one molecule and partial
positive charge on the carbonyl carbon of another
molecule.

of comparable molecular weights

due to lack of
bonding
124

. This is due to the presence of two

electron releasing groups around the carbonyl carbon
which makes them more polar.
Q.Boiling points of carbonyl compounds(aldehyde and
ketones) are higher than those of alkanes due to:
A. hydrogen bonding

B. dipole-dipole interactions

C. van der Waals' forces

D. all of the above

125

Example 1: For example, butanal and butanone both have a

molecular mass (MM) of 72. The boiling point of butanal is 76 °C
and of butanone is 80 °C, which is much higher than the boiling
points of diethyl ether (MM) 74, 34 °C and pentane (MM) 72, 36
°C.
 activities
126

Arrange the following compounds in increasing order

of their boiling points
CH3CHO, CH3CH2OH, CH3OCH3, CH3CH2CH3
127

lower member of aldehydes and ketones are

soluble in water
they can form hydrogen bonds with water

 However solubility decreases as the hydrocarbon part

of molecule increases.
 The aldehydes and ketones are soluble in organic

solvents such as benzene, ether and CCl4.

: as the size of the aldehyde or ketone molecule
increases, the hydrophobic hydrocarbon portion becomes
more dominant, making the molecule less soluble in water
128

 lists the boiling points and solubility's in water of several

low-molecular-weight aldehydes and ketones
129

 There are various methods that can be used to prepare

aldehydes depending upon the type and requirement
of the compounds.
1. By Oxidation of Alcohol
 The oxidation of primary alcohols results in the

formation of aldehydes
 the oxidation of secondary alcohols produces ketones.
130

The general chemical reaction for oxidation of

primary and secondary alcohol is shown as:
 Preparation of ketones..
131
132

 Aldehydes are obtained by the ozonolysis of alkenes.

In ozonolysis:
 first, an alkene reacts with an ozone molecule which
results in the formation of ozonide.
 Then the ozonide so formed reacts with zinc dust and

water which results in the formation of either aldehyde or

ketone depending on the type of hydrocarbon used.
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Ozonolysis of alkene
134
 Grignard reagents
135
136
137

Q. ____ compound will Q. By reacting

give secondary alcohol on magnesium with which
reacting compound, can
with methylmagnesium Grignard‘s reagent be
bromide? made?
a.) Butyl formate a.) Ethyl iodide
b.) 3- pentanone b.) Diethyl ether
c.) Pentanal c.) Methyl amine
d.) Methyl butanoate d.) Ethyl alcohol
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139
140
141
142
143
 Reaction of aldehyde and ketones…
144
145

N.B.
The decreasing order of the reactivity is due to steric and electronic
reasons.
 Sterically, the presence of two relatively large substituents in
ketones hinders the approach of nucleophile to carbonyl carbon
than in aldehydes having only one such substituent.
Question : Arrange the following compounds in increasing order of
their reactivity in nucleophilic addition reactions
Ethanal, Propanal, Propanone, Butanone.
Answer: The increasing order of reactivity is: butanone <
propanone < propanal < ethanal.
The reasons : Aldehydes are more reactive than ketones because
the >C=O group in aldehydes is less crowded.
146

Q. In which of the following solvent(s), aldehydes and

ketones are soluble?
A. Alcohol B. Ether C. Benzene D. All of the above
Q. Why the lower members of aldehyde and ketone
are soluble in water while higher members are
sparingly soluble or insoluble in water?
Solution
solubility decreases as the hydrocarbon chain length
increases as hydrocarbon contribute to non-polar part.