Department of Chemistry Sophomore Organic Chemistry for non

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Department of Chemistry Sophomore Organic Chemistry for non

Transcript Of Department of Chemistry Sophomore Organic Chemistry for non

Department of Chemistry
Sophomore Organic Chemistry for non-Chemistry Majors

CHEMISTRY 331 ◊ ORGANIC CHEMISTRY I

GENERAL INFORMATION Chemistry 331, Chemistry 332 and Chemistry 337 constitute the course sequence for pre-professional students (medicine, dentistry, optometry, pharmacy and other health professions), chemical engineering students and other students, not majoring in chemistry, who require a year of organic chemistry.
PREREQUISITES One year of freshman chemistry CH 121, CH 122, CH 123; or CH 221, CH 222, CH 223
ACID-BASE CHEMISTRY IN ORGANIC CHEMISTRY Bronsted-Lowry acids and bases Ka values, pKa values, equilibrium constants Predicting the positions of acid-base equilibria Predicting approximate pKa values Ranking acids in order of acid strength; ranking bases in order of base strength Acids and bases in organic chemistry Lewis acids and bases Nucleophiles and electrophiles Mechanism of an acid-base reaction
-two-electron processes; the use of curved arrow notation
ALKANES Nomenclature, structure and bonding, physical properties Stereochemistry
-structural isomerism, stereoisomerism, conformational isomerism Conformations of acyclic alkanes, cyclic alkanes including cyclohexane, monosubstituted cyclohexanes and disubstituted cyclohexanes -torsional strain, steric strain, angle strain, ring strain Conformational equilibria -equilibrium constants, composition at equilibrium
ALKENES Nomenclature, structure, bonding, physical properties Stereochemistry
-configurational isomerism, chirality, optical activity Conversion to Markovnikov alkyl halides
-hydrohalogenation, protonation, carbocations, carbocation rearrangements, regiochemistry/stereochemistry, mechanistic aspects Conversion to Markovnikov alcohols -hydration via the aqueous acid pathway, protonation, carbocations, carbocation rearrangements, regiochemistry/stereochemistry, mechanistic aspects -hydration via the oxymercuration-demercuration pathway, mercurinium ions, organomercurial alcohols, regiochemistry/stereochemistry, mechanistic aspects Conversion to anti-Markovnikov alcohols

-hydration via the hydroboration-oxidation pathway, alkylboranes, regiochemistry/stereochemistry, mechanistic aspects Conversion to vicinal-dihalides and halohydrins -cyclic halonium ions, anti-addition, regiochemistry/stereochemistry, mechanistic aspects Conversion to alkanes -catalytic hydrogenation, syn-addition, stereochemistry, mechanistic aspects Conversion to epoxides -syn-addition, stereochemistry, mechanistic aspects Conversion to vicinal-diols -using osmium tetroxide, using permanganate, stereochemistry, mechanistic aspects Conversion to aldehydes, ketones &/or carboxylic acids -oxidative cleavage using permanganate, ozonolysis
ALKYL HALIDES Nomenclature, structure, bonding, physical properties SN1 and E1 reactions
-rate laws, substituent effects, leaving group effects, solvent effects, rearrangements, stereochemistry, mechanistic aspects, competition -applications to synthesis SN2 and E2 reactions -rate laws, nucleophilicity, steric effects, solvent effects, leaving group effects, stereochemistry, mechanistic aspects, competition -applications to synthesis
ALKYNES Nomenclature, structure and bonding, physical properties Preparations of alkynes
-via the double dehydrohalogenation of alkyl dihalides, mechanistic aspects Conversion to Markovnikov vinyl halides, dihalides -protonation, vinyl cations, regiochemistry/stereochemistry, mechanistic aspects Conversion to ketones -hydration via the mercuric ion catalyzed pathway, regiochemistry/stereochemistry, keto-enol tautomerism, mechanistic aspects Conversion to alkanes and cis alkenes -via catalytic hydrogenation, stereochemistry Conversion to trans alkenes -via metal-ammonia reduction to trans alkenes, stereochemistry, mechanistic aspects Conversion to geminal dihalides, tetrahalides -stereochemistry, mechanistic aspects Chemistry acetylide ions -preparations/properties, applications to synthesis

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Department of Chemistry
Sophomore Organic Chemistry for non-Chemistry Majors

CHEMISTRY 332 ◊ ORGANIC CHEMISTRY II

GENERAL INFORMATION Chemistry 331, Chemistry 332 and Chemistry 337 constitute the course sequence for pre-professional students (medicine, dentistry, optometry, pharmacy and other health professions), chemical engineering students and other students, not majoring in chemistry, who require a year of organic chemistry.
PREREQUISITES One year of freshman chemistry CH 121, CH 122, CH 123; or CH 221, CH 222, CH 223 and CH 331
ALCOHOLS AND ETHERS Nomenclature, structure, bonding, physical properties Conversion to alkyl halides and sulfonate esters
-mechanistic aspects, applications to synthesis Conversion to alkenes
-via the acid-catalyzed dehydration of alcohols, E1 and E2 pathways, mechanistic aspects Conversion to aldehydes and ketones -oxidizing agents (Jones reagent, PCC) -oxidation of primary alcohols to aldehydes and carboxylic acids, mechanistic aspects -oxidation of secondary alcohols to ketones, mechanistic aspects Chemistry of ethers -epoxide ring opening, mechanistic aspects -Williamson ether synthesis, mechanistic aspects -acid-catalyzed cleavage of ethers, mechanistic aspects
ALDEHYDES AND KETONES Nomenclature, structure, bonding, physical properties Relative reactivities of aldehydes and ketones Conversion to alcohols
-via the addition of hydride and organometallic reagents (preparations/properties of sodium borohydride, lithium aluminum hydride, Grignard reagents, acetylide ions, organolithium compounds), mechanistic aspects Conversion to hydrates, hemiacetals, acetals -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

CARBOHYDRATES Nomenclature, structure, bonding, physical properties Aldoses, ketoses D sugars, L sugars Furanoses, furanosides, pyranoses, pyranosides Alpha and beta anomers Oxidations
-conversion to aldaric acids -conversion to aldonic acids Reductions -conversion to alditols Reducing sugars, nonreducing sugars Alpha-glycosidic linkages, beta-glycosidic linkage the constituent sugar(s) of a disaccharide; a trisaccharide; a polysaccharide

CARBOXYLIC ACIDS AND ESTERS Nomenclature, structure, bonding, physical properties Chemistry of carboxylic acids
-esterification, metal hydride reduction, mechanistic aspects Chemistry of esters
-acid-catalyzed hydrolysis, saponification, metal hydride reduction, conversion to alcohols, mechanistic aspects Fatty acids Waxes, triglycerides, fats, oils Soaps

STRUCTURE DETERMINATION Degrees of unsaturation Energy, wavelength, frequency Infrared spectroscopy
-typical vibrational modes -predicting/interpreting spectral -compound identification Proton NMR spectroscopy -shielding, deshielding -chemically equivalent protons, protons -splitting, pitchfork diagrams -predicting/interpreting spectral -compound identification

features non-chemically features

equivalent

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

Fall 2011

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Department of Chemistry
Sophomore Organic Chemistry for non-Chemistry Majors

CHEMISTRY 337 ◊ ORGANIC CHEMISTRY LABORATORY

GENERAL INFORMATION Chemistry 331, Chemistry 332 and Chemistry 337 constitute the course sequence for pre-professional students (medicine, dentistry, optometry, pharmacy and other health professions), chemical engineering students and other students, not majoring in chemistry, who require a year of organic chemistry.
PREREQUISITES One year of freshman chemistry CH 121, CH 122, CH 123; or CH 221, CH 222, CH 223; and CH 331, CH 332 or CH 334, CH 335, CH 336
ENOLATE CHEMISTRY Alkylation Aldol condensation Claisen condensation
RADICAL CHEMISTRY Conversion of alkanes to alkyl halides -one-electron processes; chain reactions; reactive intermediates; energy diagrams; mechanistic aspects Addition of hydrogen halides to alkenes and alkynes Radical polymerization
AMINES AND AMIDES Nomenclature, structure and bonding, physical properties Preparations and reactions
AMINO ACIDS Classification, nomenclature Acid-base properties of amino acids Separation techniques Electrophoresis and thin-layer chromatography

LABORATORY EXPERIMENTS
 Isolation/characterization of trimyristin from nutmeg Techniques Solid-liquid extraction, simple distillation, melting point determination
 Synthesis of salicylic acid via saponification Chemistry Ester saponification Techniques Heating under reflux, recrystallization, melting point determination, IR, NMR
 Separation of a methanol/water mixture Techniques Simple distillation, fractional distillation
 Isolation/characterization of essential oils from spices Techniques Steam distillation, liquid-liquid extraction, IR, NMR
 Synthesis of dibenzalacetone via an aldol condensation Chemistry Aldol condensation Techniques Recrystallization, melting point determination, IR, NMR
 Synthesis of benzoic acid via a Grignard reaction Chemistry Grignard chemistry Techniques Prep/handling of moisture-sensitive reagents, liquid-liquid extraction, recrystallization, melting point determination, IR, NMR
 Isolation/characterization of lactose Chemistry Benedict’s test
 Isolation/characterization of green-leaf pigments from spinach Techniques Solid-liquid extraction, liquid-liquid extraction, column chromatography, TLC

PROTEINS Classification, structure Peptide bonds; disulfide bonds Peptide synthesis

 Synthesis of 1-butene, cis-2-butene and trans-2-butene via E1 dehydration of 2-butanol Chemistry Dehydration alcohols Techniques GC

LABORATORY TECHNIQUES Melting point determination Recrystallization Extraction (solid-liquid; liquid-liquid) Chromatography (TLC; GC) Distillation (simple; fractional; steam) Preparation/handling of moisture-sensitive reagents Spectroscopy (IR; NMR)

 Synthesis of 1-butene, cis-2-butene and trans-2-butene via E2 dehydrohalogenation of 2-bromobutane Chemistry Dehydrohalogenation of alkyl halides Techniques GC

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Aspects ConversionChemistryStructureAspectsStereochemistry