mechanism summary 1

mechanism summary 1 - Chem 342 Organic Chemistry II Need to...

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Chem 342 • Organic Chemistry II Need to know Reactions and Mechanisms for Exam 03 Reactions of Aldehydes and Ketones O a hemiacetal + ROH 2 H + HO OR an acetal RO OR (+ ROH) (+ ROH) (- H 2 O) Wittig Reaction + Ph 3 P CH 2 phosphonium ylide + Ph 3 P O O Both aldehydes and ketones participate. The Wittig reagent is made from the alkyl halide by S N 2 reactions. 1,4-Addition O CH 3 NH 2 O NHCH 3 O Ph 2 CuLi O Ph Gillman Reagent 1,2-Addition O PhMgBr HO Ph then H 3 O + O PhLi HO Ph then H 3 O + Preparation of Carboxylic Acids OH O CH 3 KMnO 4 OH O KMnO 4 2 OH O OH OH O H O Tollen's Oxidation CrO 3 H 3 O + Ag 2 O NH 4 OH OH O C H 3 O + N O O MgBr OH O H 3 O + MgBr O C O OH O KMnO 4 2 O Oxidation Methods Other Methods Chem 342 page 1 Spring 2009
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Reactions of Carboxylic Acids and Derivatives R OH O SOCl 2 R Cl O R OH O NaOH then CH 3 I R OCH 3 O limited to primary alkyl halides S N 2 R OH O HA, CH 3 OH R OCH 3 O limited to inexpensive alcohol solvents - methanol and ethanol most practical Fischer Esterification
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mechanism summary 1 - Chem 342 Organic Chemistry II Need to...

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