CHEM 345 Study Guide - Midterm Guide: Ion, Leaving Group, Carbonation

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30 Oct 2014

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Chapter 18: carboxylic acids and their derivatives: carboxylic acids. Acids with electron-withdrawing groups are stronger than unsubstituted ones: decreases as the distance between electron-withdrawing groups and carboxyl group increases. Oxidation of aldehydes and primary alcohols: aldehydes: 1. H3o: primary alcohols: kmno4, oh, heat, both: h2cro4 (jones) H3o: ring oxidized to a co2h group. Hydrolysis of cyanohydrins and other nitriles: 1. Ha/hoh: cn group converted to co2h group. Carbonation of grignard reagents: co2/h3o, esters. Polar, but lack an oh, so can"t form strong h-bonds to each other low bps: other derivatives. Amides w/ ns bearing an h can form strong h-bonds to each other high bps. Nitriles (cn: the acidic protons of carboxylic acids are highly deshielded and absorb far downfield in the 10-12 region, nucleophilic addition-elimination of the acyl (carbonyl) carbon. Formation of a tetrahedral intermediate that returns to a carbonyl group after elimination.

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