12-08 - Give the C=O compound(s that could react with a...

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12/8/2010 1 Give the C=O compound(s) that could react with a single R-Li to give the alcohol shown. ? ? H O O CH 3 O O O O i ii iii iv OH OH ? ? A. i B. ii C. iii D. iv E. ii + iv F. iii + iv Give other reactants that would give the same alcohol. OH H 3 C Li 1. 2. H 3 O O Li O 1. OH Li O 1. 2. H 3 O 2. H 3 O OH H 3 C Li 1. 2. H 3 O O O OH O iii iv F. iii + iv What are oxidation and reduction in organic chemistry? C O OH C OH H H C O H oxidation oxidation reduction reduction oxidation Does the circled carbon atom gain or lose electron density when it is oxidized? A. gains electron density B. loses electron density How are C=O groups reduced and oxidized? oxidation oxidation reduction reduction C O OH C OH H H C O H LiAlH 4 LiAlH 4 or NaBH 4 H 2 CrO 4 H 2 CrO 4 (K 2 CrO 4 in H + /H 2 O) What is the mechanism of the following reaction? C O H H O H H O Cr O O O H H / H 2 O -H 2 O O H (see p 559 10e) H O Cr H O O O an ester H (see p. 559, 10e) Using the curved arrow formalism show how the chromic ester is transformed into the aldehyde. C O H H O H H O Cr O O O H H / H 2 O -H 2 O O H ? H O Cr H O O O an ester H Is the chromium (A) reduced or (B) oxidized ? Cr(VI) Cr(IV) Cr(III)
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12/8/2010 2 How are aldehydes oxidized to carboxylic acids? C O H H O H H O Cr O O O H H / H 2 O ? C O OH H O Cr H O O O How are aldehydes oxidized to carboxylic acids? C O H H O H H O H H O Cr O O O H H / H 2 O ? O O H H H O H O H H O Cr H–O O O O O H O Cr O O O H hydrate (Ch. 16) Is it possible to stop the oxidization at the aldehyde? C O OH C O H H O H H O H H Cl Cr O O O N H Pyridinium chlorochromate (PCC) H H O H O H H O Cr H–O O O O O H Chromic acid oxidation C O H H O H H PCC H O H H chromic acid (H 2 CrO 4 H + /H 2 O) O Cr O O O H O O H Table of synthetic reactions H 2 Pd/C H H Br H R O H 2 lindlar H H H OH PCC O H OH 1. BH 3 2. H 2 O 2 / OH H H OH O OH K 2 CrO 4 H /H 2 O C Br H 1. NH 2 2.
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