CH22.docx - CH 22 summary nucleophile attacks leaving group...

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CH. 22 summary: nucleophile attacks, leaving group abandons the molecule idea: we are going to work with acids and their energie Cyclic esters and amides lactone - has ester lactam - has amides nitriles - have cyano group Resonance better base: nitrogen anything that is an amide, it is more stable it is willing to give electrons, double bond character better bases donates, they are harder to leave, stronger double bonds Stability halogens are the worst bases the weakest base is the most reactive (acid chlorides are the weakest) halogens pKA L.G.: best is chloride, conjugate acid must be very reactive Resonance sp hybridized Naming add sufficient “-yl” anhydrides symmetrical: changning acid ending of carboxylic acid to word ANHYDRIDE mixed unsymmetrical: derived from 2 diff. carboxylic acids, alphabetize names, replacing word with anhydride Composition of Anhydrides Removing water Physical properties BP and MP : look at intermolecular interactions 1o and 2o amides have higher b.p’s and m.p’s than compounds with comparable weights solubility: rule of 5; dipole is soluble Sepctroscopic IR: Carbonyl Group C=O @ 1600 and 1850 1o and 2o amides have two additional absorptions one or two N-H stretching peaks at 3200 - 3400 N-H bending absorption @ 1640 good bse turns pi bond to single bond. So it becomes easier to stretch amide around 1600 Nucleophilic Acyl substitution nucleophilic attack on RCO- (acyl) group and replace leaving group amide: very strong nulceophile and very strong base Gen Rxns of Acid Chlorides
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nucleophile entered and gets rid of nucleophile use base tor remove proton
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