Aldehydes & Ketones

Chemistry II

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 Physical Properties

 More polar (C=O group) than comparable alkanes.

• Cannot H-bond to each other, so lower boiling
point than comparable alcohol, but higher than
alkanes.
• Good solvent for alcohols.
• Lone pair of electrons on oxygen of carbonyl can
accept a hydrogen bond from O-H or N-H.
• Acetone (propanone) and acetaldehyde (ethanal)
are miscible in water.
 Up to four carbon atoms aldehydes are soluble in
water. As the carbon atoms chain gets longer, their
solubility diminishes.

© 2017 Senda Knowmads High School

 Chemistry II

▪ Aldehydes and ketones present the carbonyl

group:
C=O

• Aldehydes are considered as products of partial

oxidation of primary alcohols.
In an aldehyde, an H atom is attached to a carbonyl group
O

CH3 – C – H
In a ketone, two carbon groups are attached to a carbonyl
group
O

CH3 – C – CH3
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 Aldehydes: IUPAC Nomenclature

• IUPAC: Replace -e with -al.

• The aldehyde carbon is number 1.
• If -CHO is attached to a ring, use the suffix -
carbaldehyde.

CH3 O CHO
CH3 CH2 CH CH2 C H
5 4 3 2 1
3-methylpentanal 2-cyclopentenecarbaldehyde
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 Aldehydes: Common & IUPAC nomenclature

COOH > COOR > CHO > C=O > OH > ROR > CH
• On a molecule with a higher priority functional group, C = O is oxo-
and -CHO is formyl.
• Aldehyde priority is higher than ketone.
COOH
1
O CH3 O
2
CH3 C CH CH2 C H 3
5 4 3 2 1
CHO
3-methyl-4-oxopentanal 3-formylbenzoic acid
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 Reactions of Aldehydes and Ketones

As the number of R groups

around the carbonyl carbon
increases, the reactivity of the
carbonyl compound decreases

Aldehydes and ketones are polar compounds Hydrogen

The carbonyl group is polar bond

– The oxygen end is electronegative

– Can hydrogen bond to water
– Cannot form intermolecular
– hydrogen bonds
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 Ketones: IUPAC Nomenclature

✓ Simplest ketone MUST have 3 carbon atoms so that the

carbonyl group is interior
✓ Base name: longest chain with the C=O
✓ Replace the –e of alkane name with –one
✓ Indicate position of C=O by number on chain so that C=O has
lowest possible number
✓ In cyclic ketones the carbonyl carbon is assigned number 1.
O O
O 1

CH3 C CH CH3
3 2 CH3
1 2C 3CH 4CH2OH
1 2 3 4
CH3 Br CH3
3-methyl-2-butanone 3-bromocyclohexanone 4-hydroxyl-3-methyl
2-butanone

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 Ketones: IUPAC Nomenclature

The R–C=O as a substituent is an acyl group, used with the

suffix -yl from the root of the carboxylic acid
CH3CO: acetyl; CHO: formyl; C6H5CO: benzoyl

The prefix oxo- is used if other functional groups are present

and the doubly bonded oxygen is labeled as a substituent on
a parent chain

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 Importance of aldehydes & ketones

• Acetone and methyl ethyl ketone are important solvents.

• Formaldehyde (metanal) used in polymers like Bakelite.
• Flavorings and additives like vanilla, cinnamon, artificial
butter.
• Many aldehydes and ketones with characteristic odors
occur in nature.

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 Importance of aldehydes & ketones

• Methanal (formaldehyde)) is a gas

used in aqueous solutions as
formalin to preserve tissue.
• Ethanal is produced from ethanol
in the liver causing hangover symptoms.
• Propanone (Acetone) is the simplest
possible ketone.
– Miscible with water
– Flammable
– Both acetone and
methyl ethyl ketone (MEK or butanone)
are very versatile solvents.
Used in many industries:
Food chemicals Natural food additives
Artificial additives Fragrance chemicals
Medicines Agricultural chemicals
© 2017 Senda Knowmads High School
Importance of aldehydes & ketones

© 2017 Senda Knowmads High School

Importance of aldehydes & ketones

© 2017 Senda Knowmads High School