Experiment a: Cis-Trans Conversion of Butenedioic Acid

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EXPERIMENT A: CIS-TRANS CONVERSION OF BUTENEDIOIC ACID
PRE-LAB ASSIGNMENT
1. Maleic acid is the cis version and fumaric acis is the trans version of butenedioic acid.

2.

3. See attached paper.

4. Maleic anhydride is the compound that crystalizes in part A in the experiment.

5. HCl acts as a catalyst to break one of the carbonyl group in the maleic acid which rotates the structure to form a trans structure of the butonal acid which is the fumaric acid. And it does so by donating its protons.

6.
Maleic acid
Chronic effects: mutagenic for somatic cells. May cause damage to kidneys and lungs. And may effect genetic material Ingestion: Very hazardous, may cause severe gastrointestinal tract irritation or burns and may cause severe and permanent damage to the digestive tract. May also effect behavior and may cause dizziness, muscle weakness, seizers and coma. Skin contact: Hazardous (irritant and possible burns). May cause dermatitis Inhalation: hazardous (Lung irritant)

Skin contact: slightly hazardous (permeator)
(http://www.sciencelab.com/msds.php?msdsId=9927564)
Fumaric acid
Chronic effects on humans: the substance is toxic to lungs and mucous membranes Ingestion: hazardous
Skin contact: slightly hazardous (irritant, permeator)
(http://www.sciencelab.com/msds.php?msdsId=9927173)

7.
a) Yes, you can tell the difference between the two isomers. This is because the first structure is a trans isomer and the second structure is a cis isomer. Trans isomers have a higher melting point than cis isomers. b) No we won’t be able to tell the difference between the two isomers. This is because they are enantiomers. Enantiomers have the same melting point.

8. Increased intermolecular hydrogen bonding does increase the melting point. It causes the boiling point to be elevated since the molecules are more attracted to each other and thus require more energy to break from the liquid phase.

9.

Physical constants |...
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