A Cis to Trans Conversion Essay

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Maleic acid and Fumaric acid are both compounds belonging to the carboxylic acids class. In this experiment, we formed the two isomers of 1,2-ethylenedicarboxylic acid and tested the solubility and melting points of both of these products. Both of these compounds involve a carbon-carbon double bond that is composed of one σ bond and one π bond. The overlap of sp2 hybrid orbitals forms the σ bond, and one empty p orbital forms the π bond. This process is illustrated in the figure below:
Sp2 hybrid orbitals: Unhybridized p orbital:
(3 σ bonds) (1 π bond)
_1 _1 _1 _1 Molecules with double bonds are alkenes, and they have restricted rotation around the double bond so they tend to form the cis and trans geometric
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The mixture then formed white crystals when placed in the ice bath, and only the white crystals remained after filtration. Table 2 describes observations made for part two of the experiment, and the theoretical yield of the second product formed.
Table 2: Observations made for part two
Mass of Maleic Anhydride (g) Mass of Final Product 2 (g) Theoretical Melting Point (⁰C)
7.99 3.54 300 - 302

The actual melting point observed for product 1 was 141⁰C, however, we could not determine the actual melting point for product 2 because it was higher than the thermometer could determine. The maximum temperature product 2 reached was 220⁰C. We did not perform the solubility test ourselves, but a classmate’s results show that product 1 was more soluble in water because it dissolved quicker than product 2 did.

1. Maleic acid is a cis isomer and Fumaric acid is a trans isomer of carboxylic acids.
2. It is not reasonable to perform a percent yield calculation separately for the two products because the filtrate reserved from the formation of maleic acid was used to produce fumaric acid in the second part of the experiment, and we could not determine how much maleic acid dissolved without additional data. However, because the isomers have the same molecular mass, we could perform a
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