CHM 2123 Lecture Notes - Lecture 6: Acetic Acid, Benzene, Acetic Anhydride

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Experiment 6 reductive amination of vanillin and p-toluidine. Class of organic compounds, containing an n, with a lone pair of electrons. Alkaloids natural compounds containing basic nitrogen atoms used for medicinal, europhic and/or toxic effects. N can form 3 covalent bonds and still be neutral; react with acids to form ammonium. Secondary amines are better nucleophiles than primary due to electron-donating ability of the additional alkyl group. Tertiary are not good nu b/c of increased steric hindrance caused by the 3 alkyl groups. When adding amines to alkyl compounds a problem arises. Using regular nu substitution to add amines to organic compounds is not effective because once a primary amine reacts, it forms a secondary amine which is more reactive and will react to form a further (undesired) product. Use reductive amination instead: the process of reacting an amine with a carbonyl containing compound to form an imine, then reduce the imine to its amine.

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