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Final - Fall 200611 - the ketones(carboxylic acid is not...

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11 25. (4 pts) What is the product of the following sequence of reactions? KMnO 4 , H + NaBH 4 Product + CO 2 OH OH OH OH O OH OH OH OH OH O OH OH OH a) c) b) d) Comments: This question tests oxidative cleavage and reduction of the carbonyl compounds. There are several questions of this type in the practice set: TS4: 33, 37, PE4A: 6, PE4B: 5, PE4C 1 and problems G and H on the “last homework” (see the website). KMnO 4 , H + NaBH 4 O O O OH O + CO 2 O O OH O OH OH OH Use pencil-eraser technique to place the carbonyl and –OH groups in the right position, and then reduce
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Unformatted text preview: the ketones (carboxylic acid is not reduced with NaBH 4 ). 26 . (4 pts) What is the product of the following reaction? OH OH OH Na 2 Cr 2 O 7 H 3 O + O O O O O O OH OH O OH O OH OH OH OH a) c) b) d) H Comments: This question tests oxidation of alcohols, and is analogous the “last homework”. Also compare TS4: 71. Chromium based reagents in presence of water oxidize primary alcohols to carboxylic acids, and secondary alcohols to ketones. Tertiary alcohols do not react....
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