derivsg - Carboxylic Acid Derivatives 1 Copyright Arizona...

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Unformatted text preview: Carboxylic Acid Derivatives 1 Copyright, Arizona State University Copyright, Arizona State University Carboxylic Acid Derivatives Addition/Elimination Definition : a compound which upon hydrolysis (bond breaking with water) yields a carboxylic acid, i.e. R O X R O O R O OR' R O NR' 2 R C N R O + H 2 O + H 2 O R O N R O O H 2 O acid halide anhydride ester amide nitrile + H 2 O + H 2 O + H 2 O H X + H H OR' H NR' 2 H NH 2 H H R C O OH R C O OH R C O OH R C O OH R C O OH + + + + 1 Nomenclature IUPAC priority: acid > ester > amide > nitrile > aldehyde > ketone > alcohol > amine > alkene > alkyne > halide • priority increases with increasing oxidation state, acids always highest priority 1.1 Acid Halide Nomenclature • derived from corresponding acid • suffix "-oyl halide" propanoyl chloride 3-bromobutanoyl bromide propanoic acid 3-bromobutanoic acid H 3 C CH 2 C O OH H 3 C CH 2 C O Cl CH 2 CH 2 C O OH CH 2 CH 2 C O Br H 3 C H 3 C Br Br H 3 O + H 3 O + 1.2 Anhydride Nomenclature • 2 types of anhydrides.... 1. simple anhydrides : symmetrical: named from corresponding acids from which they are derived R O R O O C H 3 C O OH C CH 3 O C H 3 C O O ethanoic anhydride ethanoic acid same H 3 O + 2 1 2 Carboxylic Acid Derivatives 2 Copyright, Arizona State University 2. mixed anhydrides : unsymmetrical: named from corresponding acids O O O R' O R O O ethanoic propanoic anhydride different 1 2 1 2 3 1.3 Ester Nomenclature (more…) • named from the acids and alcohols from which they are derived ethyl benzoate (ethyl ester of benzoic acid) ethyl, from alcohol benzoate from benzoic acid H 3 O + C O OH + HOCH 2 CH 3 C O O CH 2 CH 3 • "alcohol" part named using rules for complex substituents (stereochemistry ignored here) O O 1 3 2 4 H 3 O + OH O HO + 1 2 3 2-methylpropanoic acid 1 2 3 4 1-methylbutanol 1-methylbutyl 2-methylpropanoate 1.4 Amide Nomenclature (more…) • named from the acids from which they are derived C H 3 C O N CH 3 CH 3 N,N-dimethylethanamide H 2 N CH 3 CH 3 C H 3 C O OH O N N-ethyl-N,3-dimethylbutanamide ethanoic acid H 3 O + + 1 2 1 2 1 2 3 4 1.5 Nitrile Nomenclature • name the alkane, add "nitrile"!! (stereochemistry ignored here) CH 2 C N include this carbon when naming the nitrile C N 3-methyl-4-phenylpentanenitrile 1 2 3 4 5 propane nitrile CH 3 (stereochemistry ignored) Carboxylic Acid Derivatives 2 Copyright, Arizona State University 2. mixed anhydrides : unsymmetrical: named from corresponding acids O O O R' O R O O ethanoic propanoic anhydride different 1 2 1 2 3 1.3 Ester Nomenclature (more…) • named from the acids and alcohols from which they are derived ethyl benzoate (ethyl ester of benzoic acid) ethyl, from alcohol...
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derivsg - Carboxylic Acid Derivatives 1 Copyright Arizona...

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