Some physical and chemical properties of Maleic & Fumaric acid

HOOC

Physical/Chemical properties

Maleic acid HOOC

COOH
COOH

State Stereochemistry Melting Point Boiling Point Sulubility in water Dipole moment Stability Stereochemistry addition reaction Addition of Br2

White solid Cis form or Z form 130◦C Decompose below boiling point at 135◦C 79 g/100 ml at 25◦C More Lower stability of Stereoselective reaction

Fumaric acid White solid Trans form or E form 287◦C 200◦C sublime 0.7 g/100 ml at 25◦C Less Higher stability Stereoselective reaction

Kolbe electrolysis H2O/H+ at high T & P

d/l mixture of dibromosuccinic acid via non Meso dibromosuccinic acid via non classical C+ through trans addition classical C+ through trans addition Produce acetylene Produce acetylene HO Produce Malic acid

COOH Produce Malic acid HOOC Bromosuccinic acid on Produce Maleic acid treatment with aqueous alkali/heat Reaction with alkaline Meso-Tartaric acid KMnO4 pKa Values pKa1 1.92, pKa2 6.23 Dei-Alder reaction with Cis-1,2,3,6-Tetrahydrophthalic acid butadiene Optical activity Optically inactive Catalytic Produce succinic acid Hydrogenation Addition of HBr Produce Bromosuccinic acid Stereo relation Geometrical diastereomer H-Bonding Intramolecular Anhydride formation Form anhydride on heating Dipole moment of their Dipole moment of diethylmaleate is 2.54D ethyl derivatives Symmetry Less symmetrical Heat of combustion 22.7 kj/mol higher than trans (-1355 kj/mol) Density 1.59 g/cm3 Boiling point of their 225◦C ethyl derivatives

Produce fumaric acid

d/l Tartaric acid pKa1 3.02, pKa2 4.38 Trans-1,2,3,6-Tetrahydrophthalic acid

Optically inactive Produce succinic acid

Produce Bromosuccinic acid Geometrical diastereomer Intermolecular Do not form anhydride Dipole moment of diethylfumarate is 2.38D More symmetrical Lower 1.635 g/cm3 218◦C

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