Ch_12_rxn_summary

Ch_12_rxn_summary - CHEM 3053 - Chapter 12 Reaction Summary...

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CHEM 3053 - Chapter 12 Reaction Summary Know - oxidation/reduction and calculation of oxidation state Know - carbonyl reduction I. Reduction of carbonyls a. LiAlH 4 (LAH) LiAlH 4 reduces any C=O Acids, esters and aldehydes afford 1° alcohols Ketones afford 2° alcohols b . NaBH 4 NaBH 4 only reduces aldehydes and ketones Aldehydes afford 1° alcohols Ketones afford 2° alcohols Can selectively reduce aldehyde and/or ketone in presence of acid or ester. II. Oxidation of Alcohols a. Primary Alcohol to Aldehyde PCC is the only oxidant we’ve covered that stops the oxidation at the aldehyde All other oxidants oxidize 1° alcohols to acids b. Primary Alcohols to Carboxylic Acids Both KMnO 4 and H 2 CrO 3 are powerful oxidants Oxidation does not stop at aldehyde Oxidation continues to acid R Y O Y = OH, OR' or H LiAlH 4 THF R OH R R' O LiAlH 4 THF R R' OH R H O NaBH 4 MeOH R OH R R' O NaBH 4 MeOH R R' OH R H O PCC CH 2 Cl 2 R OH R OH O KMnO 4 or H 2 CrO 3 H 2 O R OH
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This note was uploaded on 12/22/2011 for the course CHEM 3053 taught by Professor Laurashirtcliff during the Fall '11 term at Oklahoma State.

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Ch_12_rxn_summary - CHEM 3053 - Chapter 12 Reaction Summary...

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