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Overview of Carbonyl Compounds. CO. No leaving ... - Chemistry

1 Ove r vie w of Ca r bo n yl C o mp ou nds . 1. Kinds of Carbonyl Compounds. a) Aldehydes and ketones RCOH and R2CO. No leaving group attached to Carbonyl C. Oxidation state +2. b) Carboxylic acids and their derivatives: esters, amides, acyl chlorides, acyl anhydrides (RCO-O-COR). One leaving group attached to Carbonyl C. Oxidation state +3. Nitriles are honorary members of the carboxylic acid family, and have much the same reactivity. c) Carbonates (RO- CO-OR) and their derivatives: urethanes (carbamates, H2 NCOOR), ureas (H2 NCONH2). Two leaving groups attached to Carbonyl C. Oxidation state +4. d) CO2. 2. Reactivity of Carbonyl compounds. a) Basic at O. O reacts with H+ or other Lewis acids such as BF3, etc. Not much else. b) Electrophilic at Carbonyl C. Under basic conditions, reacts as is. Under acidic conditions, O is protonated to give a compound even more electrophilic at C. c) Acidic at -C ( CHR2 COR ). Acidic because of electrophilic nature of Carbonyl C.

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