Chap13 - Carboxylic Acid Derivatives OMIT 13.3A, 13.3C,...

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Carboxylic Acid Derivatives OMIT 13.3A, 13.3C, 13.4, 13.6, 13.9-13.10
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NOMENCLATURE Remove "ic acid" from acid name and replace with the following endings: 1. For acid chlorides- "yl chloride." 2. For amides- change "oic acid" to "amide." Substituents attached to N in amides get "N-" numbering. 3. For anhydrides- "ic anhydride" or name1"ic" name2"ic anhydride" for two different acids bonded together as anhydride (removal of water). 4. Name esters like salts of acids. The group attached directly to the carbonyl carbon gives the acid fragment its name. The fragment attached to oxygen now gets a substituent-like name rather than a cation name (ie. 4-chlorobenzyl or isopropyl ). Result: 4-chlorobenzyl 2- methylbutanoate .
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C O C l 2-methyl-3-hexenoyl chloride an acid chloride NO 2 C Cl O NH CH 2 CH 3 5-chloro-N-ethyl-2-nitrobenzamide an amide
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C O O C O 2-methyl-3-butenoic 2-methylpropanoic anhydride an anhydride CO 2 O isopropyl 1-oxo-3-hexen-5-yne-2-carboxylate an ester
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NUCLEOPHILIC ACYL SUBSTITUTION Electronegative neighbors hate living next door to carbonyl because carbonyl carbon is always hungry for electrons (its spouse is always hogging all its electrons). When you are hungry for electrons yourself (electronegative) it doesn't help to have your neighbor looking through your garbage for any loose electron scraps you may have thrown out. Amine and carbanion like living next door to
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This note was uploaded on 12/28/2011 for the course CHEM 2060 taught by Professor Hogan during the Fall '08 term at LSU.

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Chap13 - Carboxylic Acid Derivatives OMIT 13.3A, 13.3C,...

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