chapter21 - Chapter 21 Carboxylic Acid Derivatives...

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Unformatted text preview: Chapter 21. Carboxylic Acid Derivatives: Nucleophilic Acyl Substitution Reactions Based on McMurry’s Organic Chemistry , 7 th edition Items with an asterisk (*) were covered in lecture. Items with an asterisk (*) were covered in lecture. 2 You can’t just wish for a good grade. You You can’t just wish for a good grade. You have to know the basics. have to know the basics. 3 *Carboxylic Compounds *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) 4 * * General Reaction Pattern General Reaction Pattern Nucleophilic acyl substitution Why this Chapter? Carboxylic acids are among the most widespread of molecules. A study of them and their primary reaction “nucleophilic acyl substitution” is fundamental to understanding organic chemistry 5 21.1 Naming Carboxylic Acid 21.1 Naming Carboxylic Acid Derivatives 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 6 Naming Acid Anhydrides, RCO Naming Acid Anhydrides, RCO 2 2 COR' 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 7 Naming Amides, RCONH Naming Amides, RCONH 2 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 8 Naming Esters, RCO Naming Esters, RCO 2 2 R’ R’ Name R’ and then, after a space, the carboxylic acid (RCOOH), with the “-ic acid” ending replaced by “-ate” 9 * * Nomenclature Priorities: Nomenclature Priorities: Highest priority at Highest priority at top of table and lowest priority at the bottom. top of table and lowest priority at the bottom. Function Group Suffix Name Prefix Name acid chlorides-oyl chloride ? amides-amide ? esters-oate ? carboxylic acids-oic acid ? aldehydes-al oxo ketones-one oxo alcohols-ol hydroxy phenols-ol hydroxy thiols-thiol mercapto alkenes-ene alkenyl alkynes-yne alkynyl alkanes-ane alkyl 10 * * Ester Nomenclature (RCO Ester Nomenclature (RCO 2 2 R’) R’) Prefix name = Prefix name = Suffix Name = oate Suffix Name = oate Compound Compound IUPAC Name IUPAC Name Common Name Common Name HCO 2 CH 2 CH 3 ethyl methanoate ethylformate CH 3 CO 2 CH 2 CH 2 CH 3 propyl ethanoate propylacetate CH 3 CH 2 CO 2 CH 3 methyl propanoate CH 3 CH 2 CH 2 CO 2 CH 2 CH 3 ethyl butanoate Ph-CO 2 CH 2 CH 3 ethyl benzoate ethyl benzoate Know how to use IUPAC rules and the common names in red type. 11 * * Amide Nomenclature (RCONHR’)...
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