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Pre-Lab Questions: 1. A sample of 2-butanol has a specific rotation of +3.25. Determine the optical purity (%ee) and percent composition of this sample (see Mohrig section 17.4). The specific rotation of pure (+)-2-butanol is +13.0°. 2. The equation for the formation of the diastereomeric salts is shown in the background information (performed in Part A of the procedure). Write this chemical equation in your notebook, then ALSO write a balanced equation for the formation of (+)-ibuprofen from the (5,5) salt when it is reacted with H2SO4 (performed in Part of the procedure). Special Instructions a-Phenylethylamine readily reacts with carbon dioxide in the air. Every effort should be taken to avoid prolonged exposure of the amine to air. Be sure to close the bottle tightly after you have obtained your amine. Wear gloves when dispensing the amine, as it is irritating to the skin. Be sure to note your complete observations along with your data while you work. BACKGROUND INFORMATION: The ability to produce enantiomerically pure compounds is crucial to the fine chemicals industries (pharmaceuticals, agrochemicals, fragrances, etc). This ability is probably most important to the pharmaceutical industry, where approximately 80% of the drugs under development are chiral. Enantiomerically pure compounds can be produced by one of two methods-resolution and asymmetric synthesis. Resolution is the process in which the two enantiomers of a racemic mixture are separated. Asymmetric synthesis involves the use of a chiral reagent or catalyst to create a new optically active molecule. experiment, you will separate a racemic mixture of ibuprofen into its R and S enantiomers. Ibuprofen belongs to a class of pharmaceuticals called non-steroidal anti- inflammatories, or NSAIDs. It is the active ingredient in Motrin and Advil, along with their generic equivalents. It is primarily used for pain relief and fever reduction of the two enantiomers, only one, the (5)-(+)-enantiomer, has the desired pharmacological activity, while the Renantiomer is inactive. Since the (R)-enantiomer is not harmful, most commercial CHEM 220 Golden West College 103

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optical pwrity = observed speific rotation specific rotation of the enantiomey 3.25° = 0.25 = 25% pure орьсо разity - 3 25" eneess optically pure means 25% of the mixture is of that enantiomers and 151. is racemic mixture % Composition = 75% +25% = 62.5%