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Ch_322b_18.10 - Chapter 18.10 lecture note

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Relative Reactivity of Acyl Compounds in Nucleophilic Substitution React ions The electron-withdrawing influence and l eaving group ability of X in acyl compounds leads to a general reactivity order: In general, a less reactive acyl compound can be prepared from a more reactive acyl compound. Accordingly, acyl chlorides can be converted into any of the other acyl compounds General Synthetic Scheme RC- Cl O = acyl chloride RC- OCR O = O = acid anhydride RC- OR' O = ester RC- NR'R'' O = amide > > > RCOOH RC- Cl O =
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Acyl Chlorides Because of their great reactivity, acyl chlorides must be prepared under conditions that exclude exposure to good nucleophiles. Common reagents that convert carboxylic acids into acyl chlorides are phosphorous trichloride (PCl 3 ) phosphorous pentachloride (PCl 5 ), and thionyl chloride (SOCl 2 ). Typical Synthetic Procedures The carboxylic acid is heated with the reagent (a liquid), with or without the presence of an inert solvent.
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