The Carbonyl Group

A Carbon atom double bonded to an Oxygen atom

o Polar Covalent Bond

Aldehydes & Ketones have this carbonyl group

The Carbonyl group is polar
o Oxygen = Partial negative
o Carbon = Partial positive

Geometry: Trigonal Planar; 120 degrees

Compounds Containing a Carbonyl Group

Aldehydes: Carbonyl attached to at least one H atom

Ketones: Carbonyl attached to two or more Carbon atoms

Carboxylic Acids: Carbonyl Carbon atom attached to Hydroxyl

group
Esters: Carbonyl Carbon atom attached to an Oxygen atom
Amides: Carbonyl Carbon atom attached to a Nitrogen atom

Aldehydes & Ketones

Function Group:
o Aldehydes: Carbonyl attached to at least one H atom

o Ketones: Carbonyl group attached to two or more carbons

Cyclic Aldehydes are not possible but Cyclic Ketones are possible
o Ketones can have rings because there is no H at the end
o Cyclic Ketones are not heterocyclic ring systems

Nomenclature for Aldehydes

1. The longest parent chain includes the carbon atom of the
carbonyl group
2. Name the parent chain like how alkenes are named, but change
the e ending to al
a. Methanal, Ethanal, Propanal, Butanal, Pentanal, etc.
3. Carbonyl carbon is number 1 (1 is understood, so do not put it in
the name)
4. Identify any branches and put them before the parent chain
name
Examples:

2-Methylpropanal

2-Ethylpentanal

2,3-Dichlorobutanal

Nomenclature for Ketones

1. The longest parent chain includes the carbon atom of the
carbonyl group
2. Name the parent chain by changing e to one
a. Methanone, Ethanone, Propanone, Butanone, Pentanone,
etc.
3. Number the chain so the carbonyl group is the lowest possible
number
4. Put a number before the parent chain name to indicate its
location
5. Name any branches and put them before the parent chain name
6. If there are rings, the Carbon atom of the carbonyl group is
number 1, and go in the direction that gives the lowest possible
number to the branches
Examples:

2-Hexanone
2,4-Dimethyl-3-

Pentanone

Cyclobutanone

3-Hydroxyl-4-methylcyclohexanone

Physical Properties of Aldehydes & Ketones

o Physical state at room temperature
o Aldehydes
C1-C2 are gases
C3-C11 straight-chain are liquids
More than C11 are solids
o Ketones
Low molar mass ketones are colorless liquids
No gas
o Boiling & Melting Points
o They both are intermediate between alcohols & alkanes
Higher than alkanes, lower than alcohols
o Higher boiling point than alkanes due to dipole-dipole
attractions between the carbonyl groups
o Solubility
o Water molecules can hydrogen-bond with aldehydes &
ketones, and causes it to be water soluble
o If the alkene group attached to the functional group of
aldehydes & ketones increases, it becomes less soluble or
insoluble
As you increase in size, polarity decreases, so
solubility decreases
How
o
o
o

Aldehydes & Ketones Are Made

Aldehydes are produced by mild oxidation of PRIMARY alcohols
Ketones are produced by mild oxidation of SECONDARY alcohols
Oxidizing agents: KMnO4 & K2Cr2O7

Oxidation & Reduction Reactions of Aldehydes & Ketones

o Aldehydes readily undergo oxidation to turn into carboxylic acids
o Ketones cannot be oxidized

o Tests that oxidize aldehydes:

o Tollens Test
o Benedicts Test

o Reduction Reaction of Aldehydes & Ketones

o They can be reduced with Hydrogen gas (H2) & a catalyst
o Catalysts: Ni, Pt, or Cu
o Double bond of carbonyl group opens up, & H attaches to
them
Aldehydes turn into PRIMARY alcohols
Ketones turn into SECONDARY alcohols
Examples:

Reaction of Aldehydes & Ketones with Alcohols

o A Hemiacetal: C is attached to OH & -OR group