Ester Rxns - CA DERIVATIVES Chemistry Specialist Alicia...

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CA DERIVATIVES ESTER RXNS a) Hydrolysis R OR' O R OH O b) Alcoholysis - Transesterification R OR" O H+ or NaOH R OR' O H+ or NaOR" Chemistry Specialist: Alicia Hart UC Davis - SASC R"OH, c) Ammonolysis/Aminolysis R OR' O R NH 2 O NH 3 d) Alkylation R OR' O R R" OH 1. R"Li or R"MgX, Ether - given 2 eq. of the organometallic reagent, does alkylation twice by kicking off the OR' and reforming the carbonyl. R" 2. H 3 O + i) Organometallic Reagents e) Reduction R OR' O R H OH 1. LiAlH
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Unformatted text preview: 4 , ether 2. H 3 O + H To stop at aldehyde, use less reactive red. agent. .. 1. DIBAH, Ether 2. H 3 O + R H O- Note: DIBAL aka DIBAH aka DIBAL-H stands for diisobutyl aluminium hydride. H 2 O, R'OH R'OH R'OH R'OH R'OH R'OH ii) Alkylation OR' O 1. LDA, THF 2. R"X R OR' O R R" NR NaBH 4 EtOH- if NaOH is used, carboxylate ion is formed not carboxylic acid....
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  • Spring '08
  • Nasiri
  • Chemistry, Carboxylic acid, Amide, Lithium aluminium hydride, Hydride

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