INTRODUCTION
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.
QUESTIONS
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
The literature values of erythro-2,3-dibromo-3-phenylpropanoic acid and threo-2,3-dibromo-3-phenylpropanoic acid were provided in the laboratory experiment text. Erythro-2,3-dibromo-phenylpropanoic acid held a melting point of 204°C, while threo-2,3-dibromo-3-phenylpropanoic acid held a melting point of 95°C. These two products had vastly different melting point values, which made it clear to observe the product created at the end of the experiment. Once the product was determined due to comparison of melting points, the stereochemistry could be
The mixture was transferred to an ice bath to crystallize the product, after which the product was collected by vacuum filtration on a Hirsch funnel, washing the flask with small aliquots of cold xylene and pouring the solution over the crystals, allowing the vacuum to thoroughly dry the product. Additional drying was achieved by transferring the product to filter paper and pressing the crystals to remove any excess moisture. The product was then weighed and a melting point determined. A comparative TLC was run in Hexanes:Ethyl Acetate solvent against maleic anhydride to verify the purity of the
Experiment 55 consists of devising a separation and purification scheme for a three component mixture. The overall objective is to isolate in pure form two of the three compounds. This was done using extraction, solubility, crystallization and vacuum filtration. The experiment was carried out two times, both of which were successful.
4- chlorobenzoic acid which was the aqueous layer has a theoretical melting point of 240-243°C, the organic layer, 4-chlorobenzyl alcohol has a theoretical melting point of 68-71°C. During our experiment we were unable to collect any data for the organic
Topics concerning transgender can be very overwhelming for some. When one thinks of the term transgender, one may think of the process of an individual identifying as the opposite sex. The opposite sex of what he or she was born as. For some, this may involve undergoing surgical procedures or taken hormonal medications to fulfill their desire. However, when thinking of this process, one automatically thinks of transgender adults. This is rarely a topic that one would assume would be racing through the minds of young children, but in fact it is. More children today than ever, are either speaking out about their identity concerns, or displaying it in their lives. In fact, according to Date Line NBC, “The handful of American doctors who specialize
The combination of a carbonyl (C=O) group and hydroxyl (−OH) group on the same carbon atom results in the formation of a carboxyl (−COOH) functional group. Compounds containing at least one carboxyl functional group are commonly known as carboxylic acids, and have the general molecular formula CnH2n+1COOH. Carboxylic acids with two or more carboxyl groups are called dicarboxylic acids, tricarboxylic acids, etc. The carboxyl group is one of the most frequently occurring functional groups in chemistry and biochemistry. Apart from the carboxylic acids, the carboxyl group also parents a large family of related compounds called carboxylic acid derivatives (amides, esters, thioesters, acyl halides, anhydrides, etc.)
After 10 minutes the reaction liquid was separated from the solid using a vacuum filtration system and toluene. The product was stored and dried until week 2 of the experiment. The product was weighed to be 0.31 g. Percent yield was calculated to be 38.75%. IR spectra data was conducted for the two starting materials and of the product. Melting point determination was performed on the product and proton NMR spectrum was given. The IR spectrum revealed peaks at 1720 cm-1, which indicated the presence of a lactone group, and 1730 cm-1, representing a functional group of a carboxylic acid (C=O), and 3300cm-1, indicating the presence of an alcohol group (O-H). All three peaks correspond with the desired product. A second TLC using the same mobile and stationary phase as the first was performed and revealed Rf Values of 0.17 and 0.43for the product. The first value was unique to the product indicating that the Diels-Alder reaction was successful. The other Rf value of 0.43 matched that of maleic anhydride indicating some
Discussion: As seen in the melting point determination, the average melting point range of the product was 172.2-185.3ºC. The melting points of the possible products are listed as 101ºC for o-methoxybenzoic acid, 110ºC for m- methoxybenzoic acid, and 185ºC for p- methoxybenzoic acid. As the melting point of the sample
The week after, a recrystallization was performed on the previous week’s crude product. The product ethereal solution was first heated on a steam bath until dry. During the heating, a beaker of methanol was collected and also placed on the steam bath. Once the product was dry, it was cooled to room temperature and then placed in an ice-water bath. The now boiling methanol was added to the crude crystals and a recrystallization was performed. Once completed, the now purified product was collected via Buchner vacuum filtration and stored in drawer to dry for a week. Afterwards, a melting point range of the purified product was obtained by using a Mel-temp apparatus. Lastly, an
Solubility – Very soluble (water), Freely soluble (methylene chloride, chloroform, alcohol), Slightly soluble (acetone) and Insoluble (ether).6 Melting point - 120°C or 248°F.5
Purpose: The purpose of the experiment was to perform the acid-catalyzed Fischer Esterification of acetic acid and isopentyl alcohol to form isopentyl acetate, or banana oil, which is used in flavor industries. The equilibrium of the reaction was changed by adding an excess amount of acetic acid. The reaction was refluxed and product was purified by extraction and distillation. Isopentyl acetate was analyzed by infrared spectroscopy and 1H NMR spectroscopy.
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We can see that the structural formula of a carboxylic acid can be written two ways. On the left (1), it shows all the carbon, hydrogen and oxygen bonds, while on the right (2), the carbon atom is represented by a
Conformational isomers differ in the relative position of some of the atoms in the molecule in 3Dimensional-space due to the rotation about sigma bonds.