Humboldt-Universität zu Berlin - Faculty of Mathematics and Natural Sciences - Department of Chemistry

Structure and Reactivity of Organic Compounds, Part 1

Formation and reactions of radicals: Hydrocarbons,cracking, dissociation energies, radical chain, chlorination, selectivity.

Nucleophilic substitution: Alcohols, ether, thiols, amines. Leaving Groups, nucleophiles, HSAB concept, kinetics, reaction order, transition states, electronic and steric effects, carbocations, mesomerism.

Elimination reactions: Alkenes, alkines. Mechanisms, nucleophilic substition vs. elimination, regioselectivity, stereoelectronics.

Electrophilic addition: Bromonium ions, stereoelectronics, regioselectivity, hydroboration, carbenes.

Chemistry of aromatic compounds: Aromatics, polycycles, heterocycles, aromaticity, properties associated with aromaticity, antiaromaticity. Electrophilic Substitution, σ-complex, mesomerism, Friedel-Crafts alkylation and acylation, disubstitution, selectivity, directing effects, formylation, chloromethylation, sulfonation, kinetic vs. thermodynamic Control. Nucleophilic aromatic substitution, activating groups, Sandmeyer-type reactions, elimination-addition-mechanism. Azocoupling, pigments, metalation.

Chemistry of carbonyl compounds I: Aldehydes and ketones. Nucleophilic addition, hydration, acid-base-catalysis, acetals, imines, hydrazones, oximes, hydrazides, vinylogous carbonyl groups, addition to nitriles, reduction, Meerwein-Ponndorf-Verley, Canizarro, Leuckart-Wallach, heteroanalogous carbonyl compounds.

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