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Maleic and Fumaric Acid

Maleic acid and fumaric acid are cis-trans geometric isomers that have different physical and chemical properties. Maleic acid exists as the cis form and has a lower melting point and boiling point than the trans fumaric acid. Maleic acid is more soluble in water and has a higher dipole moment. Fumaric acid is more stable and its stereochemistry leads to stereoselective reactions. The two acids also differ in properties such as heat of combustion, density, and boiling points of their ethyl derivatives.

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Siddarth Singh
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7K views1 page

Maleic and Fumaric Acid

Maleic acid and fumaric acid are cis-trans geometric isomers that have different physical and chemical properties. Maleic acid exists as the cis form and has a lower melting point and boiling point than the trans fumaric acid. Maleic acid is more soluble in water and has a higher dipole moment. Fumaric acid is more stable and its stereochemistry leads to stereoselective reactions. The two acids also differ in properties such as heat of combustion, density, and boiling points of their ethyl derivatives.

Uploaded by

Siddarth Singh
Copyright
© Attribution Non-Commercial (BY-NC)
We take content rights seriously. If you suspect this is your content, claim it here.
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Download as PDF, TXT or read online on Scribd
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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 130C Decompose below boiling point at 135C 79 g/100 ml at 25C More Lower stability of Stereoselective reaction

Fumaric acid White solid Trans form or E form 287C 200C sublime 0.7 g/100 ml at 25C 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 225C 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 218C

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