INTERCONVERSION OF SUGARS

Glucose, fructose and mannose are interconvertible in weak alkaline solutions such as Ba (OH)2 or Ca (OH)2. It is because weak alkaline solution of sugars undergo molecular change known as tautomerization.

Tautomerization Tautomerization where H atoms migrate from one carbon to another to form enediol compounds.

LOBRY de BRUYN VAN EKENSTEIN REACTION.

All sugars give the same enediolwhich tautomerizes to all three sugars. This interconversion of sugars by the action of dilute alkaliis referred to as LOBRY de BRUYN VAN EKENSTEIN REACTION.

Principle

SELIWANOFFS TEST
a chemical test which distinguishes between aldose and ketose sugars is based on the fact that, when heated, ketoses (e.g. fructose) are more rapidly dehydrated than aldoses

 Prepare four test tubes and label Place 2 ml of glucose solution to each test tube 1,2 Place 2 ml fructose to test tube 3,4 Add 1 ml saturated barium hydroxide to test tube 1,3 Add 1 ml of water to test tube 2,4 Get 0.5 ml portions from each, and do with Seliwanoffs test Add two drops of toluene to all of the mixture Set aside

Procedure

Laboratory Results
Test Tube Before After

Glucose + Ba (OH)2
Glucose + water

Light pink
Light pink

Red
Light pink Dark red Dark red

Fructose + Ba (OH)2 Cherry red Glucose + water Cherry red

Standard Results
Test Tube Glucose + Ba (OH)2 Glucose + water Fructose + Ba (OH)2 Glucose + water Before orange to amber Light orange Cherry red Cherry red After Deep cherry red Light orange Orange to Amber Red Explanation Glucose and Fructose when allowed to stand for sometime in the presence of a weak alkali is converted into a mixture containing all three sugars at an equilibrium proportion of each via the tautomeric change called Lobry de Bruyn transformation