General Formula of Carbohydrates
Cx(H2O)y Classical representation of carbohydrates as hydrates of carbon.
applies whenHas exceptions: some carbohydrates (e.g., rhamnose, C6H12O5) do not fit, and some non-carbohydrates (e.g., acetic acid, C2(H2O)2) do.
carbohydratesgeneral_formula
CHO−(CHOH)4−CH2OH+5(CH3CO)2O→CHO−(CHOCOCH3)4−CH2OCOCH3+5CH3COOH Reaction with acetic anhydride yields glucose pentaacetate, confirming five -OH groups.
applies whenAnhydrous conditions.
acetylationesterificationpentaacetate
Mild Oxidation of Glucose
CHO−(CHOH)4−CH2OHBr2/H2OCOOH−(CHOH)4−CH2OH Oxidation with bromine water yields gluconic acid, proving the carbonyl is an aldehyde.
applies whenRequires a mild oxidizing agent like Br2 water.
oxidationmildgluconic_acid
Glucose reaction with HCN
CHO−(CHOH)4−CH2OH+HCN→CH(OH)(CN)−(CHOH)4−CH2OH Reaction forming a cyanohydrin, proving the presence of a carbonyl group.
applies whenOccurs with the open-chain form of glucose.
cyanohydrinnucleophilic_additionglucose
Reduction of Glucose with HI
CHO−(CHOH)4−CH2OHΔ,HICH3−(CH2)4−CH3 Prolonged heating of glucose with hydrogen iodide yields n-hexane, proving its 6-carbon straight chain.
applies whenProlonged heating with concentrated HI.
reductionglucosestructure_elucidation
Strong Oxidation of Glucose
CHO−(CHOH)4−CH2OHHNO3COOH−(CHOH)4−COOH Oxidation with nitric acid yields saccharic (glucaric) acid, proving the presence of a primary alcohol.
applies whenRequires a strong oxidizing agent like HNO3.
oxidationstrongsaccharic_acid
Glucose reaction with Hydroxylamine
CHO−(CHOH)4−CH2OH+NH2OH→CH=NOH−(CHOH)4−CH2OH+H2O Reaction confirming the presence of a carbonyl group via oxime formation.
applies whenOccurs with the open-chain form of glucose.
carbonyl_additionoximeglucose
Enzymatic Hydrolysis of Maltose
C12H22O11+H2OMaltase2C6H12O6 Hydrolysis of maltose catalyzed by the enzyme maltase.
applies whenPhysiological/enzymatic conditions.
enzymemaltosehydrolysis
Mutarotation Equilibrium Specific Rotation
[α]eq=[α]αXα+[α]βXβ Calculation of the specific rotation of an anomeric mixture at equilibrium.
applies whenAqueous solution allowed to reach dynamic equilibrium.
mutarotationanomersjee-advanced
C6H12O6+3PhNHNH2ΔGlucosazone+PhNH2+NH3+2H2O Reaction of reducing sugars with excess phenylhydrazine to form an osazone. Glucose, fructose, and mannose form the exact same osazone.
applies whenExcess (3 equivalents) of phenylhydrazine is required.
osazonephenylhydrazinejee-advanced
Commercial Preparation of Glucose
(C6H10O5)n+nH2O393 K,H+2−3 atmnC6H12O6 Hydrolysis of starch or cellulose yielding n molecules of glucose.
applies whenBoiled with dilute H2SO4 at 393 K under 2-3 atm pressure.
hydrolysisstarchpolysaccharides
C12H22O11+H2OH+C6H12O6(Glucose)+C6H12O6(Fructose) Hydrolysis of cane sugar yielding equimolar glucose and fructose (invert sugar).
applies whenBoiled with dilute HCl or H2SO4 in alcoholic solution.
hydrolysissucrosedisaccharides