OA2 - Organic Compounds Containing Oxygen

Carbonyl to alcohol

Sodium borohydride in alkaline conditions

Acid chloride + alcohol —>

ester + hydrogen chloride

alcohol + hydrogen halide (usually created in situ using sodium halide and conc. sulphuric acid) —>

halogenoalkane + water

Phenol + sodium hydroxide —>

sodium phenoxide + water

Phenol + (hydrogen)carbonate —>

No reaction

Test for phenol

add iron(III) chloride solution, which produces a purple color.

Phenol + sodium (or more reactive metals)

Sodium phenoxide + hydrogen

Test for aldhehydes

Tollen’s reagent (ammonical silver nitrate) gives a silver mirror (and/or grey precipitate)

Test for aldhehydes

Add Fehlings reagent which produces a red precipitate (of copper(I) oxide)

Mechanism of producing nitriles from carbonyls

Nucleophilic addition

Test for carbonyls

addition of a few drops of the unknown to 2,4-dinitrophenylhydrazine (2.4, DNPH) solution produces an orange precipitate

Iodoform test (test for 2^o alcohols or methyl ketones)

Add iodine and enough sodium hydroxide to remove the colour. A yellow precipitate (CHI₃) is a positive result.

Carboxylic acid to alcohol

add lithium aluminium hydride in dry ether

Decarboxylation

Removal of the carboxylic acid group using soda lime (sodium hydroxide solution and calcium oxide)

Nitrile to amine

Add lithium aluminium hydride in dry ether

Halogenoalkane to nitrile

Add sodium/potassium cyanide in ethanol

Nitrile to carboxylic acid

Add water and acid (HCl) or base (NaOH - produced sodium salt)

Carboxylic acid to amide

Add ammonium carbonate and then heat to dehydrate the salt.

Carbonyl to Hydroxynitrile

Add sodium/potassium cyanide to a carbonyl compound in the presence of a dilute acid.

Amide to nitrile

Add phosporous(V)oxide and water is given off.