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ws9_SS11_alkenes&alkynesIII_pt2

ws9_SS11_alkenes&alkynesIII_pt2 - Oxidative...

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CHE321 Summer 2011 Alkenes & Alkynes III Workshop 9 June 28, 2011 1. Tartartic acid is a diprotic organic acid which played an important role in the discovery of chirality in chemical compounds. It occurs naturally in many plants and is one of the main acids found in wine. Tartaric acid can by synthesized by dihydroxylation of maleic acid or fumaric acid. Maleic acid and fumaric acid are diastereomers. Dihydroxylation of maleic acid leads to meso -tartaric acid, while dihydroxylation of fumaric acid leads to a racemic mixture of ( R , R )-and ( S , S )-tartaric acid. Determine the structures of maleic acid and fumaric acid. 2. Predict and draw the structures of compounds A - I . All nine compounds are distinct.
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Unformatted text preview: Oxidative cleavage of A with hot basic potassium permanganate yields 2-methylpropanoic acid and carbon dioxide. The same oxidative cleavage of F or H yields only 2-methylpropanoic acid. Oxidation of F with osmium tetroxide produces an achiral diol, G . Bromination of H produces an achiral dibromide, I . 3. Provide a synthesis for the following racemic cyclopropyl alkane. You can use any reagent, but you must use propyne and 1-chlorobutane. Challenge Problem 4. Below is an example of hydrohalogenation involving a rearrangement. Using the curved arrow formalism, show all the bond breaking and bond making steps of the following reaction....
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