Advanced Organic Chemistry

Carbohydrates: Formation of hemiacetals.
Haworth projection. Mutarotation. Fehling and Tollens oxidation Oxidation with HIO ₄ . Oxidation with Br ₂ /H ₂ O. Oxidation with O ₂ /Pt. Reduction with NaBH ₄ . Osazone formation. Addition to hydroxyl groups. Protection of hydroxyl groups. Wohl and Ruff degradation. Synthesis of Kiliani-Fisher Disaccharides. Amino acids and peptides: isoelectric pH. HVZ synthesis. Gabriel's synthesis. Strecker synthesis. Peptide synthesis

Tools to determine a mechanism: Identify intermediates. Isotopic labeling.
Product stereochemistry. Solvent effect. Kinetic data: Kinetic equations.
Consecutive reactions. Nitration of benzene Arrhenius theory. Transition state theory. competitive reactions. Curtin-Hammet principle. Hammond principle. Isotope effect: Secondary isotope effect.

Concepts in SN2: Stereochemistry.
Solvent. Nucleophile and nucleophobic. Substrate structure. Concepts in SN1: Stereochemistry.
Solvent. Substratum. anchimeric assistance. Nonclassical carbocations. Elimination reactions: Elimination 1.4. Elimination 1.1. Elimination 1.3. Fragmentation. E1 (Unimolecular elimination). E2 (bimolecular elimination). E1cb. Stereochemistry of elimination reactions. Regiochemistry of elimination reactions. pyrolytic removals. Elimination of Hofmann and Cope

Formation of single bonds: Alkylation of enamines.
Imines and lithiated enamines. Stereoselective alkylation. aldol condensation. Michael and Robinson. Claisen condensation. Acetylacetic and malonic synthesis. Formation of dianions. Umpolung reactions. Formation of double bonds: Pyrolysis of esters.
Elimination of Cope. Hofmann elimination. Sulfoxide removal. Sulfoxide-sulfenate rearrangements. Wittig reactions. Wittig. Wadsword-Emmons. Horner-Wittig. Peterson. Sulfur ylides. Shapiro. Diels-Alder: Regiochemistry.
Carbenes and radicals: Synthesis of carbenes: Elimination 1,1.
Decomposition of diazo compounds.
Decomposition of tosylhydrazones. Reactivity of carbenes: Cyclopropanation.
Simmons-Smith reaction. CH insert. Arndt-Eistern. Hofmann and wolf transposition.

Oxidation of benzylic H.
Oxidation of H. allylics. Oxidation of alcohols: chromic.
manganese dioxide. Alkoxysulfonium salts. Swern oxidation. Oppenaver oxidation Olefin oxidation: Prevost reaction.
Woodward's reaction. Alkene epoxidation. Epoxy opening. ozonolysis. Oxidation with periodic acid. Oxidation of ketones: Oxidation to alpha-hydroxyketones.

Reduction reactions: Acyloinic condensation. Non-metallic hydrides. Clemmensen. Wolff-kishner. thioacetals Alkynes with Na/NH3. Birch reduction. Obtaining 1,2-symmetrical diols