Org Chem II Chap 21 - Chapter 21. Carboxylic Acid...

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Chapter 21. Carboxylic Acid Derivatives: Nucleophilic Acyl Substitution Reactions Org Chem II Schrock UWF
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Carboxylic Compounds Acyl group bonded to X, an electronegative atom or leaving group Includes: X = halide (acid halides), acyloxy (anhydrides), alkoxy (esters), amine (amides), thiolate (thioesters), phosphate (acyl phosphates) Org Chem II Schrock UWF
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General Reaction Pattern Org Chem II Schrock UWF
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Naming Carboxylic Acid Derivatives Acid Halides, RCOX Derived from the carboxylic acid name by replacing the - ic acid ending with - yl or the - carboxylic acid ending with – carbonyl and specifying the halide Org Chem II Schrock UWF
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Naming Acid Anhydrides, RCO 2 COR' If symmetrical replace acid” with “ anhydride”  based on the related carboxylic acid From substituted monocarboxylic acids: use bis - ahead of the acid name Unsymmetrical anhydrides— cite the two acids alphabetically Org Chem II Schrock UWF
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Naming Amides, RCONH 2 With unsubstituted NH 2 group. replace - oic  acid or - ic acid with - amide , or by replacing the - carboxylic acid ending with – carboxamide If the N is further substituted, identify the substituent groups (preceded by “N”) and then the parent amide Org Chem II Schrock UWF
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Naming Esters, RCO 2 R’ Name R’ and then, after a space, the carboxylic acid (RCOOH), with the “- ic acid” ending replaced by “- ate” Org Chem II Schrock UWF
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Nucleophilic Acyl Substitution Carboxylic acid derivatives have an acyl carbon bonded to a group Y that can leave A tetrahedral intermediate is formed and the leaving group is expelled to generate a new carbonyl compound, leading to substitution Org Chem II Schrock UWF
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Substitution in Synthesis Readily convert a more reactive acid derivative into a less reactive one Reactions in the opposite sense are possible but require more complex approaches Hydrolysis to acid and conversion to acid chloride is easiest method Org Chem II Schrock UWF
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General Reactions of Carboxylic Acid Derivatives
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This note was uploaded on 08/02/2011 for the course CHM 2045 taught by Professor Geiger during the Spring '08 term at University of Central Florida.

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Org Chem II Chap 21 - Chapter 21. Carboxylic Acid...

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