Learning Goals

1 Draw the structures and discuss the physical

properties of aldehydes and ketones.

2 From the structures, write the common and
I.U.P.A.C. names of aldehydes and ketones.

3 Write equations for the preparation of
aldehydes and ketones.

4 Write equations representing the oxidation of
carbonyl compounds.

5 Write equations representing the reduction of
carbonyl compounds.

Introduction
Carbonyl compound: Any
compound that contains a
carbonyl group (C=O).
Carbonyl groups are strongly
polarized, with a partial
positive charge on carbon
and partial negative charge
on oxygen.


Carbonyl compound
Polarity of carbonyl group contributes to its reactivity.
C=O bond is shorter, stronger, and more polar than C=C bond
in alkenes.
Carbonyl compounds are broadly divided into two groups:
aldehydes and ketones are in one group and the second group
contains carboxylic acids, esters, acid chlorides and amides.
Nomenclature
Properties
Preparation reactions of Aldehydes and
Ketones
Characteristic reactions of Aldehydes and
Ketones
Aldehydes and Ketones
- Both aldehydes and ketones contain carbonyl group C=O

- The difference between aldehyde and ketone was found to be:
In aldehyde C=O attach with H and R i.e
In ketone C=O attach with two R
C O
R
R
I.U.P.A.C. Nomenclature and Common Names

1. Determine the parent compound, that is, the longest
continuous carbon chain containing the carbonyl group.

2. Replace the final -e of the parent alkane with -al.

3. Number the chain beginning with the carbonyl carbon
(or aldehyde group) as carbon-1.

4. Number and name all substituents as usual.

Naming Aldehydes

Examples
CH
3
CH
2
CH
CH
3
CH
2
C H
O
CHO
3-methylpentanal
1-cyclopentenemethanal


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9
Nomenclature Aldehyde Common Names
The simplest aldehydes are known by their
common names:

formaldehyde, HCHO
acetaldehyde, CH3CHO
benzaldehyde, C6H5CHO

Use the I.U.P.A.C. and common nomenclature systems to name
each of the following compounds.

Common Aldehydes
Formaldehyde, HCHO: Toxic but useful. It kills viruses, fungi
and bacteria. It is used in disinfecting and sterilizing
equipment. The polymerization property of formaldehyde is
utilized in adhesives and for binding plywood.

Acetaldehyde (CH
3
CHO): Sweet smelling. Present in ripe
fruits, especially in apples. It is less toxic than formaldehyde.

Benzaldehyde, C
6
H
5
CHO, is commonly known as almond oil.
It is used in cooking.

Formaldehyde
Gas at room temperature.
Formalin is a 40% aqueous solution.
O
C
O
C
O
C
H
H
H
H
H
H
heat
H C
O
H
H
2
O
H C
H
OH
HO
trioxane, m.p. 62C
formaldehyde,
b.p. -21C
formalin
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Naming Ketones

1. The -e ending of the parent alkane is replaced with
the -one suffix of the ketone family.
2. The location of the carbonyl carbon is indicated with a
number.

Examples
CH
3
C
O
CH
CH
3
CH
3
O
Br
CH
3
C
O
CH
CH
3
CH
2
OH
3-methyl-2-butanone
3-bromocyclohexanone
4-hydroxy-3-methyl-2-butanone
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Ketone Common Names
Some ketones are also known by their
common names. These are the names of the
two alkyl groups (usually alphabetized)
bonded to the carbonyl group followed by the
word ketone.
methyl ethyl ketone (MEK)
CH
3
CH
2
COCH
3
acetone CH
3
COCH
3


Use the I.U.P.A.C. and common nomenclature systems to name
each of the following compounds.

Acetone (CH
3
COCH
3
): It is one of the most
widely used solvents. It can dissolve most
organic compounds and is also miscible with
water. Acetone is highly volatile and highly
flammable.

Common Ketones
Boiling Points
More polar, so higher boiling point than
comparable alkane or ether.
Cannot H-bond to each other, so lower
boiling point than comparable alcohol.
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Examples
Arrange the following in order of increasing
boiling point.
pentanal
2-pentanol
ethyl isopropyl ether
pentane

Solubility
Good solvent for alcohols.
Lone pair of electrons on oxygen of
carbonyl can accept a hydrogen bond from
O-H or N-H.
Acetone and acetaldehyde are miscible in
water.

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Preparation of Aldehydes and Ketones

Summary of reactions disscussed in earlier chapter that
yield of ketones and aldehydes.
a. Ozonolysis of alkenes
b.Hydration of alkynes
c.Friedel-Crafts acylation of aromatic
d.Oxidaton of alcohols to aldehydes or ketones
e.Other useful methods