Department of Chemistry
DEPARTMENT OF CHEMISTRY
Sophomore Organic Chemistry for non-Chemistry Majors
CHEMISTRY 331 ◊ ORGANIC CHEMISTRY I
GENERAL INFORMATION Conversion to anti-Markovnikov alcohols Chemistry 331, Chemistry 332 and Chemistry 337 constitute the -hydration via the hydroboration-oxidation pathway, course sequence for pre-professional students (medicine, alkylboranes, regiochemistry/stereochemistry, mechanistic dentistry, optometry, pharmacy and other health professions), aspects chemical engineering students and other students, not majoring in Conversion to geminal-dihalides and halohydrins chemistry, who require a year of organic chemistry. -cyclic halonium ions, anti-addition, regiochemistry/stereochemistry, mechanistic aspects COURSE STRUCTURE PREREQUISITES Conversion to alkanes Four credit-hour course One year of freshman -catalytic hydrogenation, syn-addition, stereochemistry, Thirty one hour lectures chemistry mechanistic aspects Ten one hour recitations CH 121, CH 122, CH 123; or Conversion to epoxides CH 221, CH 222, CH 223 -syn-addition, stereochemistry, mechanistic aspects Conversion to geminal-diols ACID-BASE CHEMISTRY IN ORGANIC CHEMISTRY -using osmium tetroxide, using permanganate, Bronsted-Lowry acids and bases stereochemistry, mechanistic aspects Ka values, pKa values, equilibrium constants Conversion to aldehydes, ketones &/or carboxylic acids Predicting the positions of acid-base equilibria -oxidative cleavage using permanganate, ozonolysis Predicting approximate pKa values Ranking acids in order of acid strength; ranking bases in order of ALKYL HALIDES base strength Nomenclature, structure, bonding, physical properties Acids and bases in organic chemistry SN1 and E1 reactions Lewis acids and bases -rate laws, substituent effects, leaving group effects, solvent Nucleophiles and electrophiles effects, rearrangements, stereochemistry, mechanistic Mechanism of an acid-base reaction aspects, competition -two-electron processes; the use of curved arrow notation -applications to synthesis SN2 and E2 reactions ALKANE -rate laws, nucleophilicity, steric effects, solvent effects, leaving Nomenclature, structure and bonding, physical properties group effects, stereochemistry, mechanistic aspects, Stereochemistry competition -structural isomerism, stereoisomerism, conformational -applications to synthesis isomerism Conformations of acyclic alkanes, cyclic alkanes including ALKYNES cyclohexane, monosubstituted cyclohexanes and disubstituted Nomenclature, structure and bonding, physical properties cyclohexanes Preparations of alkynes -torsional strain, steric strain, angle strain, ring strain -via the double dehydrohalogenation of alkyl dihalides, Conformational equilibria mechanistic aspects -equilibrium constants, composition at equilibrium Conversion to Markovnikov vinyl halides, dihalides Conversion to alkyl halides -protonation, vinyl cations, regiochemistry/stereochemistry, -one-electron processes; chain reactions; reactive mechanistic aspects intermediates; energy diagrams; mechanistic aspects Conversion to ketones -hydration via the mercuric ion catalyzed pathway, ALKENES regiochemistry/stereochemistry, keto-enol tautomerism, Nomenclature, structure, bonding, physical properties mechanistic aspects Stereochemistry Conversion to alkanes and cis alkenes -configurational isomerism, chirality, optical activity -via catalytic hydrogenation, stereochemistry Conversion to Markovnikov alkyl halides Conversion to trans alkenes -hydrohalogenation, protonation, carbocations, carbocation -via metal-ammonia reduction to trans alkenes, rearrangements, regiochemistry/stereochemistry, mechanistic stereochemistry, mechanistic aspects aspects Conversion to geminal dihalides, tetrahalides Conversion to Markovnikov alcohols -stereochemistry, mechanistic aspects -hydration via the aqueous acid pathway, protonation, Chemistry acetylide ions carbocations, carbocation rearrangements, -preparations/properties, applications to synthesis regiochemistry/stereochemistry, mechanistic aspects -hydration via the oxymercuration-demercuration pathway, mercurinium ions, organomercurial alcohols, regiochemistry/stereochemistry, mechanistic aspects
June/2006 Page 1 of 3
DEPARTMENT OF CHEMISTRY
Sophomore Organic Chemistry for non-Chemistry Majors
CHEMISTRY 332 ◊ ORGANIC CHEMISTRY II
GENERAL INFORMATION CARBOHYDRATES Chemistry 331 (lecture), Chemistry 332 (lecture) and Chemistry Nomenclature, structure, bonding, physical properties 337 (lecture and laboratory) constitute the course sequence for Aldoses, ketoses pre-professional students (medicine, dentistry, optometry, D sugars, L sugars pharmacy and other health professions), chemical engineering Furanoses, furanosides, pyranoses, pyranosides students and other students, not majoring in chemistry, who Alpha and beta anomers require a year of organic chemistry. Oxidations -conversion to aldaric acids COURSE STRUCTURE PREREQUISITES -conversion to aldonic acids Four credit-hour course One year of freshman chemistry Reductions Thirty one hour lectures CH 121, CH 122, CH 123; or -conversion to alditols Ten one hour recitations CH 221, CH 222, CH 223 Reducing sugars, nonreducing sugars and Alpha-glycosidic linkages, beta-glycosidic linkage CH 331 the constituent sugar(s) of a disaccharide; a trisaccharide; a polysaccharide ALCOHOLS AND ETHERS Nomenclature, structure, bonding, physical properties CARBOXYLIC ACIDS AND ESTERS Conversion to alkyl halides and sulfonate esters Nomenclature, structure, bonding, physical properties -mechanistic aspects, applications to synthesis Chemistry of carboxylic acids Conversion to alkenes -esterification, metal hydride reduction, conversion to ketones, -via the acid-catalyzed dehydration of alcohols, E1 and E2 mechanistic aspects pathways, mechanistic aspects Chemistry of esters Conversion to aldehydes and ketones -acid-catalyzed hydrolysis, saponification, metal hydride -oxidizing agents (Jones reagent, PCC) reduction, conversion to alcohols, mechanistic aspects -oxidation of primary alcohols to aldehydes and carboxylic Fatty acids acids, mechanistic aspects Waxes, triglycerides, fats, oils -oxidation of secondary alcohols to ketones, mechanistic Soaps aspects Chemistry of ethers STRUCTURE DETERMINATION -epoxide ring opening, mechanistic aspects Degrees of unsaturation -Williamson ether synthesis, mechanistic aspects Energy, wavelength, frequency -acid-catalyzed cleavage of ethers, mechanistic aspects Infrared spectroscopy -typical vibrational modes ALDEHYDES AND KETONES -predicting/interpreting spectral features Nomenclature, structure, bonding, physical properties -compound identification Relative reactivities of aldehydes and ketones Proton NMR spectroscopy Conversion to alcohols -shielding, deshielding -via the addition of hydride and organometallic reagents -chemically equivalent protons, non-chemically equivalent (preparations/properties of sodium borohydride, lithium protons aluminum hydride, Grignard reagents, acetylide ions, -splitting, pitchfork diagrams organolithium compounds), mechanistic aspects -predicting/interpreting spectral features Conversion to hydrates, hemiacetals, acetals -compound identification -via the addition of water and alcohols, acetals as protecting groups in synthesis, mechanistic aspects Conversion to imines -via the addition of ammonia and its derivatives, mechanistic aspects
AROMATICITY AND CHEMISTRY OF BENZENE Nomenclature, structure, bonding, physical properties Aromaticity Electophilic aromatic substitutions -halogenation, nitration, sulfonation, Friedel-Crafts alkylation, Friedel-Crafts acylation, mechanistic aspects Clemmensen reduction Wolff-Kishner reduction
June/2006 Page 2 of 3
DEPARTMENT OF CHEMISTRY
Sophomore Organic Chemistry for non-Chemistry Majors
CHEMISTRY 337 ◊ ORGANIC CHEMISTRY LABORATORY
GENERAL INFORMATION LABORATORY EXPERIMENTS Chemistry 331 (lecture), Chemistry 332 (lecture) and Chemistry 337 (lecture and laboratory) constitute the course sequence for ¾ Melting point determinations pre-professional students (medicine, dentistry, optometry, Techniques Melting point determination pharmacy and other health professions), chemical engineering students and other students, not majoring in chemistry, who ¾ Isolation/characterization of trimyristin from nutmeg require a year of organic chemistry. Techniques Solid-liquid extraction, simple distillation, melting point determination COURSE STRUCTURE PREREQUISITES Four credit-hour course One year of freshman chemistry ¾ Isolation/characterization of green-leaf pigments from Ten four-hour labs CH 121, CH 122, CH 123; or spinach Nine eighty minute CH 221, CH 222, CH 223; Techniques Solid-liquid extraction, liquid-liquid extraction, lectures (relevant and column chromatography, TLC chemistry and laboratory CH 331, CH 332 or techniques) CH 334, CH 335, CH 336 ¾ Isolation/characterization of lactose Nine eighty minute Chemistry Benedict’s test lectures (topics listed below) ¾ Isolation/characterization of essential oils from spices Techniques Steam distillation, liquid-liquid extraction, IR, ENOLATE CHEMISTRY NMR Alkylation Aldol condensation ¾ Synthesis of 1-butene, cis-2-butene and trans-2-butene via Claisen condensation E1 dehydration of 2-butanol Chemistry Dehydration alcohols RADICAL CHEMISTRY Techniques GC Addition of hydrogen halides to alkenes Radical polymerization ¾ Synthesis of 1-butene, cis-2-butene and trans-2-butene via E2 dehydrohalogenation of 2-bromobutane AMINES AND AMIDES Chemistry Dehydrohalogenation of alkyl halides Nomenclature, structure and bonding, physical properties Techniques GC Preparations and reactions ¾ Synthesis of salicylic acid via saponification AMINO ACIDS Chemistry Ester saponification Classification, nomenclature Techniques Heating under reflux, recrystallization, melting Acid-base properties of amino acids point determination, IR, NMR Separation techniques Electrophoresis and thin-layer chromatography ¾ Synthesis of dibenzalacetone via an aldol condensation Chemistry Aldol condensation PROTEINS Techniques Recrystallization, melting point determination, Classification, structure IR, NMR Peptide bonds; disulfide bonds Peptide synthesis ¾ Synthesis of benzoic acid via a Grignard reaction Chemistry Grignard chemistry LABORATORY TECHNIQUES Techniques Prep/handling of moisture-sensitive reagents, Melting point determination liquid-liquid extraction, recrystallization, Recrystallization melting point determination, IR, NMR Extraction (solid-liquid; liquid-liquid) Chromatography (column; TLC; GC) ¾ Synthesis of 9,10-dihydroanthracene-9,10-α,β-succinic acid Steam distillation anhydride via a Diels-Alder reaction Preparation/handling of moisture-sensitive reagents Chemistry Diels-Alder reaction Spectroscopy (IR; NMR) Techniques Vacuum filtration, recrystallization, IR, NMR
¾ Asymmetric reduction of 1-phenyl-1,2-propanedione Chemistry Asymmetric reduction Techniques TLC, liquid-liquid extraction, IR and NMR June/2006 Page 3 of 3