CHEM 22200 Lecture Notes - Lecture 4: Acetic Acid, Benzene, Transesterification

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Cl aldehyde ketone carboxylic ester amide acid chloride acid. C n acid anhydride thioester nitrile ubiquitous functional group in chemistry and biology. O pka ~ 4-5 resonance stabilized carboxylate anion; these resonance structures are equivalent and both contribute equally. In these structures, the negative charge resides on the highly electronegatice oxygen. This stabilizes the anion and makes carboxylic acids relatively acidic. Carboxylic acids are more highly oxidized than most other organic compounds. Thus, they are often accessed from other compounds by oxidation: oxidation of alkenes (8. 17) R (b) (1) kmno4, oh, (2) h3o+ Oh: oxidation of aldehydes and primary alcohols (16) +, oh (1) kmno4, oh, (2) h3o+ Preparation of carboxylic acids, continued: oxidation of the benzene ring (15. 13) Arrange the following aromatic compounds in order of decreasing nucleophilicity (decreasing reactivity in electrophilic aromatic substitution) Arrange the following compounds in order of decreasing electrophilicity (decreasing reactivity towards nucleophiles)