COOH slides - Chapter 21. Carboxylic Acid Derivatives and...

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Chapter 21. Carboxylic Acid Derivatives and Nucleophilic Acyl Substitution Reactions Based on McMurry’s Organic Chemistry , 6 th edition
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Carboxylic Compounds Acyl group bonded to Y, an electronegative atom or leaving group Includes: Y = halide (acid halides), acyloxy (anhydrides), alkoxy (esters), amine (amides), thiolate (thioesters), phosphate (acyl phosphates)
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General Reaction Pattern Nucleophilic acyl substitution
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21.1 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
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Naming Acid Anhydrides, RCO 2 COR' If symmetrical replace acid” with “ anhydride” based on the related carboxylic acid (for symmetrical anhydrides) From substituted monocarboxylic acids: use bis - ahead of the acid name Unsymmetrical anhydrides— cite the two acids alphabetically
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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
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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”
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21.2 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
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Relative Reactivity of Carboxylic Acid Derivatives Nucleophiles react more readily with unhindered carbonyl groups More electrophilic carbonyl groups are more reactive to addition (acyl halides are most reactive, amides are least) The intermediate with the best leaving group decomposes fastest
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Substitution in Synthesis We can readily convert a more reactive acid derivative into a less reactive one Reactions in the opposite sense are possible but require more complex approaches
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This note was uploaded on 02/22/2011 for the course CHEM 311 taught by Professor Johnson during the Spring '11 term at SUNY Geneseo.

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COOH slides - Chapter 21. Carboxylic Acid Derivatives and...

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