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- (S)-2-Butanol, CH3CH2CHOHCH3, slowly racemizes on standing in dilute aqueous sulfuric acid. Explain, illustrating with a mechanism.Aldohexoses A and B both undergo Ruff degradation to give aldopentose C. On treatment with warm nitric acid, aldopentose C gives an optically active aldaric acid. B alsoreacts with warm nitric acid to give an optically active aldaric acid, but A reacts to givean optically inactive aldaric acid. Aldopentose C is degraded to aldotetrose D, whichgives optically active tartaric acid when it is treated with nitric acid. Aldotetrose D isdegraded to (+)@glyceraldehyde. Deduce the structures of sugars A, B, C, and D, and useFigure 23-3 to determine the correct names of these sugars.Name the structure. Heating compound A in the presence of H2SO4 results in which product?
- The (+) - aureol is a natural product that has shown selective activity against certain colon and lung cancer cell lines. It is postulated that a key step in the biosynthesis of this substance is the conversion of carbocation A into B. Propose a possible mechanism for this transformation (MUST show the corresponding arrows).tert-Butoxycarbonyl azide was developed as a reagent for peptide synthesis at OWL's home institution, the University of Massachusetts, by Prof. L.A. Carpino. It is prepared by treating tert-butoxycarbonyl chloride with sodium azide. Propose a structure for the initially-formed intermediate in this reaction.4.4 Show how the compound thiodiazine - C21H26N2S2 - decomposes anaerobically and how these end products in turn decompose aerobically to stabilized sulfurand nitrogen compounds.
- the following reaction scheme leads to the formation of compound C. give the structure of the final product C and of the intermediate products A and B and justify, using the mechanism, the formation of the product A. Give the serereochemistry of the final product obtainedSeveral steps in the synthesis of optically active duloxetine, an antidepressant sold under the trade name Cymbalta, are shown. Identify the structure of intermediates A–C and the final product duloxetine, including stereochemistry, in this reaction sequence.Several steps in the synthesis of optically active duloxetine, anantidepressant sold under the trade name Cymbalta, are shown. Identifythe structure of intermediates A–C and the final product duloxetine,including stereochemistry, in this reaction sequence.
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