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Stereochemistry of Butenedioic acid

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Introduction

Name: Tonny, Chan Kar Yu, Student ID: 10297729 Date of Experiment: 19th February 2005, Group: B1 Title: Stereochemistry of Butenedioic acid Objective: To study the interconversion of two geometric isomers, maleic acid (cis isomer) to fumaric acid (trans isomers), the differences in physical properties between this pair of cis-trans isomers and determine the stereochemistry of addition of bromine to butenedioic acid. Chemicals and Apparatus: 2 grams of maleic acid, 10 cm3 of concentrated hydrochloric acid, 10 cm3 of bromine water1, one 50 cm3 beaker, one 100 cm3 beaker, one 250 cm3 beaker, one 10 cm3 measuring cylinder, one piece of spatula, one piece of water glass, one glass rod, a few pieces of filter paper, a set of Buchner funnel, a filter flask with side tube, three glass capillary tubes, a set of melting point apparatus, one long hollow glass tubing, one electronic balance, one heater and the oven Background: Stereochemistry is always encountered throughout organic chemistry. And stereochemistry isomerism can be divided into two classes, geometrical isomerism and optical isomerism. Although these categories are not mutually exclusive, it is not uncommon to find compounds that exhibit only one or the other of the two types. Most geometrical isomers result from cyclic systems or restricted rotation about double bonds. The preparation of fumaric acid by isomerization of maleic acid and addition of molecular bromine to fumaric acid was illustrated in the experiment. Geometric isomers can be interconverted if the double bond is temporarily converted to a single bond, about which rotation is relatively free. ...read more.

Middle

3. White precipitates would be formed after 10 minutes and the colour of the mixture would be turned to light yellow. If the solution became colourless as it was being heated, a few milliliters of the bromine solution was added. 4. The solution was removed from the heat and cooled in an ice bath. 5. The product was collected by suction filtration as the setup in part A. The crystals was washed about 1 cm3 of cold water and dried the crystals by drawing air through them for a few minutes. 6. The crystals was transferred into a weighed watch glass and dried in an oven at about 120 for 10 minutes. 7. The dried crystals of 2,3-dibromosuccinic acid was weighed. 8. The melting points of two isomers were measured and recorded using the electrical melting point apparatus. Results: A. Conversion of maleic acid to fumaric acid Mass of maleic acid used = 2.004 g Mass of fumaric acid used = 1.651 g Percentage yield Melting point of maleic acid: 138 Melting point of fumaric acid: 254 B. Addition of Bromine to Fumaric Acid Mass of fumaric acid used = 1.001 g Mass of 2,3-dibromosuccinic acid(dried) = 1.3858 g Percentage yield = no. of mole of C4H4O4Br2 / no of mole of C4H4O4 Melting point of 2,3-drbromosuccinic acid: 255 Discussion: Geometrical isomer is a stereomer which is superposable with its own mirror image. However, a pair of diastereomers is not mirror images of each other. ...read more.

Conclusion

When the small beaker in the water bath was removed, we MUST not place it in the ice water immediately because it is very dangerous as the beaker would crack and the solution will bounce out. We should cool the solution to room temperature and then place it to ice water to make the solution much saturated. The solubility of fumaric acid is much insoluble than maleic acid since there is no net dipole moment in fumaric acid. When placing the beaker in the lower temperature environment, more fumaric crystal would be formed by saturation. Conclusion: In the experiment, we had to make sure that all water was evolved from the sample and all remaining substance was pure, otherwise, the percentage yield in the result would become meaningless. Hazards The whole experiment part B had to process in the fume cupboard as bromine gas is toxic and has strong disagreeable odor, and having a very irritating effect on the eyes and throat. Maleic acid is a strong toxic; we have to use gloves while handling this compound and concentration hydrochloric acid is corrsive. Avoid contact them with face and hands. Solid compounds from the experiment should be placed into the appropriate labeled waste jars in the side hood. 1 The stock solution of bromine water was prepared by dissolving 232.5 g of Br2 and 187.5 g KBr in water and diluting to about 750 ml. ?? ?? ?? ?? College Chemistry (250-06) Tonny, Chan Kar Yu Laboratory Report Group: B1, Student ID: 10297729 - 1 - ...read more.

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Here's what a teacher thought of this essay

5 star(s)

A very high level account of isomerism. This goes into much detail and is explained beautifully. There are some answers to commonly asked questions at the end of the report

Overall, this report is 5 stars out of 5.

Marked by teacher Brady Smith 10/04/2013

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