ALDEHYDES and KETONES

Uniting feature: Carbonyl group ( C=O )

Difference: Aldehyde Ketone

ALDEHYDES

Representatives

Some medically useful Aldehydes

a. Formalin Embalming agent (i.e. germicide, fungicide, insecticide)

b. Chloral anesthetic and precursor for chloroform (by application of heat and alkali)
c. Urotropine disinfectant for urinary antiseptics

Oxidation Reactions

a. Aldehyde + acidified KMnO4 Brown ppt. (MnO2)

RCHO + 2KMnO4 + H2SO4 RCOOH + K2SO4 + 2MnO2 + H2O
b. Aldehyde + Tollens reagent silver mirror (Ag)
RCHO + 2AgNO3 + 2NH4OH RCOOH + 2Ag + NH4NO3 + H2O
c. Aldehyde + Fehlings reagent brick red precipitate (Cu2O)
RCHO + 2CuSO4 + 4NaOH RCOOH + Cu2O + 2Na2SO4 + H2O
d. Aldehyde + Schiffs reagent Magenta colored solution
Polymerization Reaction

Linear Polymerization

Cyclic Polymerization

Addition Reaction

Aldehyde + NaHSO3 White Precipitate

Milk Test

Serves as a test for the presence of formaldehyde in milk

Sample + FeCl3 + H2SO4 purple ring (+)

Preparation of Aldehyde from Primary Alcohol

RCH2OH (weak oxidizing agent) RCHO

KETONES

***Difference in structure between aldehydes and ketones affects their properties in two ways
(reactivity):

1. Aldehydes are easily oxidized while ketones can also be oxidized but with difficulty.
2. Aldehydes are usually more reactive than ketones toward nucleophilic addition.

(a) TollensTest, (b) Fehlings Test, (c) Schiffs Test and (d) addition of NaOH to ketones will
have no reaction or negative result. This illustrates the ketones being non-reactive.
(a) Addition of NaHSO3 and (b) iodoform test on the other hand, generates a positive result.

Representative

Acetone

Preparation of Acetone by Catalytic Dehydration (or oxidation) of Secondary Alcohol

 MONOCARBOXYLIC ACIDS

Representatives

Acetic acid and propionic acid have irritating odor and are liquid in form while the rest are
odorless and in solid form. It should also be noted that the degree of acidity decreases as the
hydrocarbon chain increases.

In terms of solubility, all except acetic acid are immiscible/insoluble with water. All are
miscible/soluble with organic solvents such as ether and ethanol.

Chemical Properties

1. Reaction with Alcohols (Esterification)

a. CH3COOH + CH3CH2OH (H2SO4) CH3OOCH2CH3 (ethyl acetate plastic balloon odor) + H2O

b.
2. Reaction with Ferric Salts

3 CH2COONa + FeCl3 Fe(CH3COO)3 (reddish brown ppt) + 3 NaCl

3. Millons test

Millons reagent (HgNO3 in HNO3) + Salicylic acid = reddish colored solution

This tests for the presence of phenolic group in salicylic acid. It is also used for the
determination of a specific amino acid in biochemistry.