Ketones

Ketones are organic compounds which incorporate a carbonyl functional group, C=O. The
carbon atom of this group has two remaining bonds that may be occupied by hydrogen or alkyl
substituents. If at least one of these substituents is hydrogen, the compound is an aldehyde. If neither is
hydrogen, the compound is a ketone. The general formula for ketones is R2C=O where the R- group
represents any alkyl. Examples:

CH3- CH3CH2- CH3CH2CH2- CH3CH2CH2CH2-

Methyl Ethyl Propyl Butyl

The ketones can be named systematically from the corresponding alkanes by changing the ending of
each alkane to -yl followed by the word ketone after both alkyl groups are named, as in the form methyl
ethyl ketone for CH3COCH2CH3.

The common name for a ketone may be listed by molecular weight. Methyl is chosen first because it has
a lower molecular weight than ethyl.

CH3
|
C=O
|
CH2CH3

Methyl Ethyl
Ketone

The common name may also be listed in alphabetical order

with respect to the two alkyl groups on the C=O double bond.

If both of the alkyl groups are the same the numerical prefix di- is used, as in the case of
dimethylketone. Dimethyl ketone is more commonly known by the trivial name acetone, and finds
significant use as a solvent.

CH3 CH3 CH2CH3 CH3 CH2CH3

| | | | |
C=O C=O C=O C=O C=O
| | | | |
CH3 CH2CH3 CH2CH3 CH2CH2CH3 CH2CH2CH3

Dimethyl Methyl Ethyl Diethyl Methyl Propyl Ethyl Propyl

Ketone Ketone Ketone Ketone Ketone

For all except the simplest ketones, this form is not used and the ketone group is indicated systematically
by use of the IUPAC system of nomenclature which assigns the suffix -one to ketones. Further, the
parent chain includes the carbonyl group and is numbered so that the carbonyl location is the lowest
number. The number of the location must be part of the name whenever there would be an uncertainty.

Dimethyl ketone would be named 2-propanone, while methyl ethyl ketone would be named as a
substituted butane, 2-butanone. However, in the case of both 2-propanone and 2-butanone the number
is not necessary since these ketones cannota be arranged in any other order - There is no uncertainty.

CH3 CH2CH3 CH3

CH2CH3 |
CH3 CH3 | |
| CH 3CH
| | C=O C=O
C=O |
C=O C=O | |
| C=O
| |
CH2CH3
CH3 CH2CH3 CH2CH2CH3 CH2CH2CH3 |
3- CH2CH2CH3
Propanone Butanone 2- 3- 2-Methyl-3-
Pentanone
Pentanone Hexanone Hexanone

Notice: Propanone, Dimethyl Ketone and Acetone are Identical

A ketone carbonyl function may be located anywhere within a chain or ring, and its position is given by a
locator number. Chain numbering normally starts from the end nearest the carbonyl group. In cyclic
ketones the carbonyl group is assigned position #1, and this number is not cited in the name, unless more
than one carbonyl group is present.

When the suffix form cannot be used, perhaps because another suffix such as that of a carboxylic acid is
required, the alternative designation -keto can be used for the ketone group. An example is 2-
ketopropanoic acid.

CH3
|
C=O
|
C=O
|
OH

2-Ketopropanoic Acid

A variety of oxidizing agents can be used to transform a secondary alcohol to a ketone. A common
reagent for this reaction is some form of chromium (VI) chromium in the +6 oxidation state in
acidic solution. This reagent can be prepared by adding a salt of the chromate (CrO 42-) or dichromate
(Cr2O72-) ions to sulfuric acid. Or it can be made by adding chromium trioxide (CrO 3) to sulfuric acid.
Regardless of how it is prepared, the oxidizing agent in these reactions is chromic acid, H 2CrO4.