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Chemistry Courses Topics Lists Last updated: 3/24/10 Course Name and Number: ___CHEM 2412: Organic Chemistry II_____________ Instructors: _ Clower , Hornbuckle, Kirberger _____________ List of topics that should be covered in this course: (Mechanism should be covered for each reaction listed below unless noted.) Reactions of Alkenes Addition Reactions with symmetrical addition reagents (H2, Br2, Cl2); Addition Reactions with asymmetrical addition reagents (H2O, HBr, HCl, Hg(OAc)2 and H2O then NaBH4); Markovnikov’s Rule; Carbocation Rearrangement; Anti-Markovnikov Addition (HBr and ROOR, hydroboration-oxidation); Halohydrin synthesis; Stereochemistry of addition reactions; Epoxidation; Glycol formation; Ozonolysis and oxidative cleavage by permanganate Alkynes Nomenclature and drawing of alkynes; Physical properties of alkynes; Hybridization and bond lengths, scharacter; Acidity of terminal alkynes; Acetylide formation and reactions with alkyl halides and carbonyl compounds; Elimination reactions used to form alkynes (terminal/internal isomerization); Addition reactions (H2 with and without Lindlar’s Catalyst, Br2, Cl2, H2O, HBr, HCl, oxymercurationdemercuration, HBr and ROOR, hydroboration-oxidation); Enol-keto tautomerism Structures and Synthesis of Alcohols Nomenclature and drawing of alcohols (including hydroxyalkyl groups, diols, triols); Common names of alcohol of 4 carbons or less; Primary, secondary, tertiary alcohols; Physical properties of alcohols; Phenol (very briefly); Absolute alcohol; Denatured alcohol; Acidity of alcohols and phenols; Formation of alkoxide ions; Review methods of alcohol synthesis covered in earlier chapters; Grignard reagents (reactions with ketones, aldehydes, esters, acid halides, epoxides); Functional groups that interfere with Grignard Reactions; Reduction reactions using sodium borohydride, lithium aluminum hydride, and H2 with Raney Ni; Organolithium reagents Reactions of Alcohols Oxidation of alcohols: Chromic acid reagents, PCC, Swern Oxidation (no mechanism); Formation of tosylate esters; Methods for reducing alcohols; SN1 and SN2 reactions; Lucas Reagent; PX3 (with stereochemistry); SOCl2 (with stereochemistry); Dehydration reactions reviewed; Pinacol Rearrangement; Esterification of alcohols (Fischer esterification, acid chlorides); Williamson ether synthesis Aromatic Compounds Benzene structure and stability; Historical structure deduction (Kekulé); Unusual reactions of benzene; Resonance stabilization; Aromatic, Antiaromatic and Nonaromatic compounds; Huckel’s Rule; Aromatic ions; Pyridine, pyrrole, furan; Nomenclature and drawing of benzene derivatives (including phenyl and benzyl groups); Physical properties of aromatic compounds Reactions of Aromatic Compounds Electrophilic Aromatic Substitution; Br2/FeBr3; Cl2/AlCl3; I2 + HNO3; Nitration; Sulfonation; Desulfonation; ortho para-directors; meta-directors; activating and deactivating groups; inductive effect and resonance effect; Friedel-Crafts Alkylation and limitations; Friedel-Crafts Acylation; Clemmensen Reduction; Gattermann-Koch Formylation; Permanganate oxidation of side chains; Halogenation in the benzyllic position Ketones and Aldehydes Carbonyl group; Ketone nomenclature and structure drawing; Aldehyde nomenclature and structure drawing; Oxo and formyl groups; Oxa groups; Carbaldehyde groups; Physical properties of ketones and aldehydes; Review ketone and aldehyde preparations covered in earlier chapters; Synthesis of aldehydes and ketones using 1,3-dithianes; Synthesis of ketones from carboxylic acids; Synthesis of aldehydes and ketones from carboxylic acids; Nucleophilic addition to aldehydes and ketones; Formation of cyanohydrins; Formation of imines (Schiff Base); Formation of hemiacetals and acetals; Acetals as protecting groups; Oxidation of aldehydes vs. ketones; Hydration of carbonyl groups reviewed; WolffKishner reduction; Clemmenson reduction reviewed Amines Chemistry Courses Topics Lists Last updated: 3/24/10 Amine nomenclature and structure drawing (including ammonium salts, amino groups); Primary, secondary, tertiary amines; Physical properties of amines: odor, boiling points, solubility, pH, intermolecular forces; Relative basicity of nitrogen containing organic compounds; Acid-base reactions; Alkylation of amines; Acylation of amines Carboxylic Acids Carboxylic acid and carboxylate salt nomenclature and structure drawing; Physical properties of carboxylic acids: odor, boiling points, solubility, pH, intermolecular forces; Relative acidity of substituted carboxylic acids; Acid-base reactions; Properties of carboxylate salts; Preparations of carboxylic acids: Oxidation of primary alcohols, Oxidative cleavage of alkenes and alkynes, Oxidation of alkyl benzenes, Carboxylation of Grignard reagents; Chemical reactions of carboxylic acids: Fischer esterification, Acid chloride synthesis, Acid anhydride synthesis, Amide synthesis, Reduction of carboxylic acids, Alkylation of carboxylic acids to form ketones – reviewed Carboxylic Acid Derivatives Acid chloride, Acid anhydride, ester, amide nomenclature and structure drawing Physical properties of acid chlorides, acid anhydrides, esters, and amides: odor, boiling points, solubility, pH, intermolecular forces; Interconversion of acid derivatives by nucleophilic acyl substitution; Transesterification; Hydrolysis of acid derivatives List of optional topics that can be taught in this course: Carbene addition to alkenes, Polymerization of alkenes Thiols Phenol synthesis using H2O2 and FSO3H, Birch Reduction Nucleophilic Aromatic Substitution Benzyne Wittig Reaction Nitrile chemistry The Hofmann Elimination The Cope Elimination Reactions of amines with nitrous acid Reactions of Arenediazonium salts The Sandmeyer reaction Reductive amination Acylation-reduction to synthesize amines