into the trans state before the double bond was reformed to create dimethyl fumarate. Weight and melting point of the crystals formed were taken for further analysis. Enantiomeric carvones were compared by odor and optical rotation for analysis. The data collected from the comparison was used to analyze the physical and chemical properties of enantiomers. 6. Data and Results Dimethyl maleate was converted to dimethyl fumarate through…
The key piece of data was the comparison between the melting point ranges of the unknown enantiomer and the known product of (2S, 3R)-2,3,-dibromo-3-phenylpropanoic acid. The mechanism which produced this product was the anti addition mechanism for the bromination of trans-cinnamic acid because the other mechanism would have produced a product with a significantly lower melting point. In order to determine the percent recovery, a mass of the completely dried crude product should have been taken.…
An object is chiral if it has a non-superimposable mirror image. Our hands are mirror images that cannot be superimposed on each other therefore they are chiral. There are objects that do have a superimposable mirror image, like a drinking glass or ball and these are known to be achiral (Morris Hein, 2013). A carbon compound needs to have four different atoms or groups attached to at least one carbon atom for it to be classified as chiral (Timberlake, 2009). Chiral compounds are also called…
Our initial investigation of the asymmetric Mannich reaction of indole 2a with phenyl α-amidosulfone 3a is summarized in Table 1. The effect of catalyst structure on the reaction outcome was first investigated at 10 mol% catalyst loading in toluene (Table 1, Entries 1–5). As we expected, based on our knowledge of the catalytic performance of chiral oligoEG 1,[7] the ether chain length (Entries 1–3) as well as suitable acidity of the phenolic protons (Entry 2 vs. Entries 4 and 5) are critical for…
CHEM 8 A Stereochemistry Report Scaffold Introduction The purpose of this experiment was to find out the absolute configuration of 1-phenylethanol. This was accomplished by using the method of competitive enantioselective conversion (CEC), where 1-phenylethanol reacts with one enantiomer of the chiral catalyst homobenzotetramisole (HBTM). The technique that was applied was thin-layer chromatography (TLC), which will determine the HBTM enantiomer that will react faster. Theory The difference…
DOPA must be administered as the pure (-) – enantiomer, this is necessary to prevent a build-up of (+) – DOPA in the body which could not be metabolized by the enzymes present. The asymmetric synthesis of DOPA is carried out on an industrial scale. The two enantiomers in many chiral compounds have distinct biological activities. Propranolol was introduced in the 1960’s and it belongs to a group of medicines known as beta-blockers. It is used to treat many different medical conditions such as…
Constitutional isomers gave the same molecular formula but different connectivity, while stereoisomers have the same connectivity but a different orientation in space. Stereoisomer has two subunits called enantiomers and diastereomers. Enantiomers are molecules that are mirror images, while diastereomers are not mirror images. Stereochemistry focus mainly on chiral centers, which is a carbon with four different substituents attached to it. Though there are different types of nuclear…
In this experiment, the competing enantioselective conversion (CEC) method was used to react an unknown secondary alcohol, which is either the R- or the S- enantiomer, with S-HBTM and R-HBTM separately. Thin-layer chromatography (TLC) was used to determine which reaction was faster. If the S-HBTM was faster, then the unknown secondary alcohol had the R configuration. If the R-HBTM was faster, then the unknown secondary alcohol had the S configuration. 1H NMR was used to determine the molecular…
Experiment #6: Polarimetry Resolution of (∓)-Racemate: (∓)-ɑ-Phenylethylamine OBJECTIVE All chiral molecules have a mirror image of themselves. While they have the same physical properties, they interact with other chiral molecules completely different. Since there are many chiral molecules in organics, this can lead to the need to make optically pure products. If the chemist does not, it can lead to many problems including death. In this experiment, the separation of two enantiomers was…
Chemistry and Psychology always fascinated me and these subjected motivated me to study and later on make career in the pharmaceutical world. In chemistry I really enjoyed studying drug topic thalidomide. Thalidomide is the two enantiomers of an optically isomeric medication had altogether diverse impacts directed independently, otherwise as a racemic blend. On account of Thalidomide, in pregnant ladies one enantiomer lightens morning sickness, which is the thing that the medication had been…