carbohydrate reaction
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aldehyde portion of glucose (bromine water)
• mild oxidation with bromine water • aldehyde->carboxylic acid • HC==O -> COOH • product: gluconic acid
aldehyde portion of glucose (NH2OH)
• nucleophilic addition-elimination (substitution) with hydroxylamine(NH2OH) • aldehyde->oxime • HC==O -> HC==NOH • O is removed, replaced with NOH • oxime is pesticide, toxic, poisonous
aldehyde portion of glucose and terminal alcohol (HNO3 -[O} )
-vigorous oxidation with warm dilute nitric acid HNO3 -[O] -aldehyde–> carboxylic acid -(primary) alcohol–> carboxylic acid -HC==O -> COOH -CH2OH -> HC==O -> COOH -product:glucaric acid(aldaric acid) ald=specify it’s originally aldehyde
aldehyde portion of glucose (NHBH4)
-reduction with sodium borohydride (NHBH4) -aldehyde–> (primary) alcohol -HC==O -> CH2OH -product: sorbitol (polyalcohol/alditol) ald=specify it’s originally aldehyde
Test for reducing or non-reducing sugar
-tollen’s reagent (silver mirror, Ag reduced) -Fehling reagent (brick red precipitate, Cu reduced) -Benedict’s reagent (brick red precipitate, Cu reduced) *positive test indicates sugar is oxidised *reducing sugar can undergo oxidation *aldehyde can further oxidised while ketone cant *therefore, all aldoses are reducing sugar while ketoses are non-reducing #exception: fructose. it reduces tollen’s because toleen’s has NH3 which is basic. Fructose is readily isomerized to an aldose in basic solution