Chapter21 - Chapter 21. Carboxylic Acid Derivatives and...

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Unformatted text preview: Chapter 21. Carboxylic Acid Derivatives and Nucleophilic Acyl Substitution Reactions Based on McMurrys Organic Chemistry , 6 th edition 2003 Ronald Kluger Department of Chemistry University of Toronto Based on McMurry, Organic Chemistry, Chapter 21, 6th 2 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) Based on McMurry, Organic Chemistry, Chapter 21, 6th 3 General Reaction Pattern Nucleophilic acyl substitution Based on McMurry, Organic Chemistry, Chapter 21, 6th 4 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 Based on McMurry, Organic Chemistry, Chapter 21, 6th 5 Naming Acid Anhydrides, RCO 2 COR' If symnmetrical 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 Based on McMurry, Organic Chemistry, Chapter 21, 6th 6 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 Based on McMurry, Organic Chemistry, Chapter 21, 6th 7 Naming Esters, RCO 2 R Name R and then, after a space, the carboxylic acid (RCOOH), with the - ic acid ending replaced by - ate Based on McMurry, Organic Chemistry, Chapter 21, 6th 8 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 Based on McMurry, Organic Chemistry, Chapter 21, 6th 9 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 Based on McMurry, Organic Chemistry, Chapter 21, 6th 10 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 Based on McMurry, Organic Chemistry, Chapter 21, 6th 11 General Reactions of Carboxylic Acid Derivatives water carboxylic acid alcohols esters ammonia or an amine an amide hydride source an aldehyde or an alcohol Grignard reagent a ketone or an alcohol Based on McMurry, Organic Chemistry, Chapter 21, 6th...
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Chapter21 - Chapter 21. Carboxylic Acid Derivatives and...

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