Ch. 20 SG - Chem 140C Chapter 20 Study Guide Order of...

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Chem 140C Chapter 20 Study Guide Order of Reactivity with Addition-Elimination Reactions 1. Acyl Halide (most reactive) 2. Anhydride 3. Ester 4. Amide (least reactive) Acyl Halides (-CXO) Can easily undergo hydrolysis by water Reacts with alcohols in the presence of base to form esters o A form of esterification Reacts with amines in the presence of base to form amides Bases like amines typically prefer to react with the acyl halide over other portions of a parent molecule Reduction of Acyl Halides React with LiAlH 4 to form a primary alcohol React with LiAl(OtBu) 3 H to form an aldehyde o Having only one hydride present makes it possible to only reduce target molecule once Organocuprates (R 2 CuLi) Made by reacting alkyl lithium with copper iodide to make a dialkyl copper lithium Only adds once to an acyl halide to make a ketone o An alternative to organometallics due to them adding twice o Acyl halide b ketone b 3 o alcohol Anhydrides (RCOOCOR) Synthesized via reaction of acyl halide and carboxylic acid
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Ch. 20 SG - Chem 140C Chapter 20 Study Guide Order of...

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