As mentioned above, the cis isomer is able dissolve completely and the trans isomer was not able to dissolve completely. The reason why these isomers differ in solubility is because the cis isomer has stronger intermolecular forces, meaning that they have dipole-dipole forces. These dipole-dipole forces allow cis isomers to dissolve in water because both water and cis isomers are polar. Whereas, the trans isomer has weaker intermolecular forces and is non-polar, which is why it does not dissolve in water. Therefore, the cis isomer has ion-dipole forces with water and the trans isomer does not, which is why the cis isomer is soluble in water.
From table above, it shows that the trans isomer has a higher melting point than the cis isomer. The
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The first step is a simple acid base reaction with the carbonyl oxygen and a proton. The proton shown as a “bare” proton, but in reality, the proton would be solvated with water. After the positive charge is formed on the oxygen atom it can then be delocalized throughout the conjugated system.” When the oxygen is protonated by adding hydrochloric acid, one of the double bonds in the carbonyl group will become a lone pair and this will increase the repulsion. Then the double bond between the two central carbons is delocalized and forms between the oxygen atom and the carbon atom. Therefore, this new double bond will resist rotation and the weakened carbon-carbon bond will not resist rotation as much. When additional heat energy is added the molecule, it will rotate from where the the bond was weakened, and this will rearrange the spatial arrangement of atoms. Although, there is a different spatial arrangement of atoms, there is a steric interaction, meaning the atoms are still joined in the same order, but are rotated. The double bond will form back with the two central carbons and the OH groups will be on separate sides of the double bond, forming fumaric