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Oxidation of Aldheydes and Ketones Essay

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Oxidation of Aldehydes and Ketones

Materials Needed

molecular model kit
2 mL cyclohexanone, 2 mL acetone, 2 mL propanal
4 mL 5% AgNO3(aq), 12 mL 5% NaOH(aq), 5% NH3(aq) or conc. NH4OH(aq)
6 mL copper(II) citrate solution (Benedict's reagent)
samples of 4-hydroxy-3-methoxybenzaldehyde, (+)-carvone, (-)-carvone

Additional Reading Assignment: Bettelheim, Chapter 15, Chapter 17


I. Structure and Physical Properties of Aldehydes and Ketones

Aldehydes and ketones both contain the C=O or carbonyl group. Aldehydes have at least one hydrogen
bonded directly to the C=O whereas ketones always have two alkyl groups attached to the C=O.
an aldehyde a ketone

Because they contain the polar carbonyl group, aldehydes and ketones are polar compounds. However, they
cannot form hydrogen bonds one to another, as do alcohols. Therefore, the boiling points of aldehydes and ketones
are less than those of alcohols of similar molecular weight, but greater than those of hydrocarbons of similar
molecular weight. The solubility of aldehydes and ketones in H2O is significant if they contain less than five
carbons. This is because hydrogen bonds to the water molecules are formed. Acetaldehyde (ethanal, CH3CHO) and
acetone are miscible with water in all proportions.

II. Chemical Properties (see Bettelheim, chapter 17.4)

Aldehydes are easily oxidized a fact due to the presence of the hydrogen attached to the carbonyl group
(this is not present in ketones, which are less easily oxidized). Oxidation of aldehydes yields carboxylic acids. Even
air will oxidize an aldehyde (eq 1).
| |
R-C=O + O2 R-C=O (1)
(aldehyde) (from air) (carboxylic acid)

Other weak oxidizing agents can bring about this reaction. One of these is Tollens' reagent, a basic (OH-
solution of the silver complex ion, Ag(NH3)
. The reaction produces metallic silver (Ag0
), which often forms a

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