Course Description
The student will be able to recognize the interrelationships between, write structures for, and state some of the physical and chemical properties of many of the organic compounds based upon functional group classifications. AAS: Physical science (laboratory science) elective.
Prerequisite(s)
CHEM 1624 with a grade of C or better
IAI Number
CHM 913
IAI Title
Organic Chemistry I
Course Fee
$40
Topical Outline
- Structure and Bonding: atomic structure, bond formation, Lewis Structures, bond polarity, formal charges, resonance, structural formulas, molecular and empirical formulas, atomic and molecular orbitals, sigma and pi bonding, hybridization and molecular shapes, bond rotation, isomerism
- Acids and Bases; Functional Groups: molecular polarity, intermolecular forces, solubility, Arrhenius and Bronsted- Lowry acids and bases, acid/base strengths, acid/base dissociation constants, equilibrium, factors affecting acidity/basicity (solvents, size, electronegativity, inductive effects, hybridization, resonance), Lewis acids/bases, electrophile, nucleophile, curved arrow formalism, functional groups (alkanes, cycloalkanes, alkenes, alkynes, aromatic, alcohols, ethers, aldehydes, ketones, carboxylic acids and derivatives, amines, amides, nitriles)
- Structure and Stereochemistry of Alkanes: molecular formulas, common and IUPAC names, primary, secondary, tertiary carbon atoms, physical properties (solubility, density, boiling point, melting point) uses and sources of alkanes, reactions (combustion, cracking, hydrocracking, halogenation), structure and conformations, Newman projections, rotation, torsional energy and steric strain, cycloalkanes and conformations, cis-trans isomerism, ring strain, stability
- The Study of Chemical Reactions: mechanisms, thermodynamics and kinetics of chemical reactions, the free- radical chain reaction as an example to apply the concepts of mechanism, equilibrium constants and free energy, enthalpy and entropy, kinetics and rate equations, activation energy and temperature dependence of rates, transition states, rate-limiting step, selectivity to the study of chemical reactions, reactive intermediates (radicals, carbocations, carbanions, carbenes) intermediate stability, Hammond’s postulate, proposing reaction mechanisms
- Stereochemistry: structural isomers, stereoisomers, chirality, enantiomers, chiral carbons and other chirality centers, mirror planes of symmetry, achiral molecules, (R) and (S) nomenclature, optical activity, (+) and (-) rotation, specific rotation, racemic mixtures, enantiomeric excess and optical purity, Fisher projections, diastereomers, cis-trans on rings and double bonds, meso compounds, absolute and relative configuration, physical properties of diastereomers, resolution of enantiomers
- Alkyl Halides: Nucleophilic Substitution: alkyl halide IUPAC nomenclature, common uses, structure, physical properties, synthesis (free-radical chain reaction, allylic bromination, allylic shift), reactions of alkyl halides, substitutions and eliminations, SN2 mechanism, factors affecting SN2 (strength of
nucleophile, substrate) stereochemistry of SN2, SN1 mechanism, factors affecting SN1(substituents, leaving group, solvent), stereochemistry of SN1, rearrangements (hydride and methyl shifts), comparison of SN1 and SN2, predicting order and products of substitution reactions - Structure and Synthesis of Alkenes; Elimination: alkenes and the double bond, sigma and pi bonds, elements of unsaturation, IUPAC nomenclature, cis-trans, E-Z nomenclature, commercial importance, physical properties, stability, cycloalkenes, synthesis of alkenes by dehydrohalogenation of alkyl halides, E1 mechanism, competition between SN1 and E1, rearrangements in E1, Zaitsev’s rule, E2 mechanism, Hoffman orientation, stereochemistry of E2, comparison of E1 and E2, competition between and predicting order and products of substitutions and eliminations, additional alkene synthesis: acid catalyzed dehydration of an alcohol mechanism, catalytic cracking and dehydrogenation of alkanes
- Reactions of Alkenes: electrophilic additions, addition of hydrogen halides, Markovnikov’s rule, free-radical addition of HBr, anti-Markovnikov additions, acid catalyzed hydration, oxymercuration-demercuration, alkoxymercuration- demurcuration, hydroboration, addition of halogens, formation of halohydrins, catalytic hydrogenation, addition of carbenes, epoxidation, acid-catalyzed opening of epoxides, syn dihydroxylation, oxidative cleavage
- Alkynes: IUPAC nomenclature of alkynes, commercial importance, structure, terminal and internal, acidity, synthesis from acetylides, addition of acetylides to carbonyls, synthesis of alkynes by elimination, reactions of alkynes, additions, hydrogenation, addition of halogens and hydrogen halides, hydration to ketones and aldehydes, keto-enol tautomerism, oxidation of alkynes (permanganate and ozonolysis)
- Structures and Synthesis of Alcohols: structure, classification, common and IUPAC nomenclature, diols, phenol, physical properties, commercial importance, acidity, formation of alkoxides, synthesis of alcohols (SN2 and acid-catalyzed hydration), organometallic reagents for alcohol synthesis, Grignard and organolithium reagents, Grignard reaction mechanism, additions to formaldehyde, aldehydes, ketones, acid chlorides and esters, reaction with ethylene oxide, Gilman reagents, reductions of carbonyls, hydride reductions, sodium borohydride and LAH, thiols, nomenclature, SN2 synthesis
- Reactions of Alcohols: oxidation states of alcohols, oxidations of primary and secondary alcohols, oxidizing agents, chromium and chromium free reagents, formation of tosylates, SN2 reactions of tosylate esters, reductions of alcohols, reaction of alcohols with hydrohalic acids, (SN1 and SN2), Lucas Reagent, reactions of alcohols with phosphorus halide, thionyl chloride, acid catalyzed dehydration of alcohol, bimolecular condensation, Pinacol rearrangement, Fischer esterification, esters of inorganic acids, nitrate and phosphate esters, Williamson ether synthesis
At the end of this course, students will be able to:
- Employ appropriate and safe laboratory techniques to perform experiments, collaborating with partners.
- Interpret the results of instruments to analyze reactions and products.
- Employ laboratory skills and content knowledge to determine the identity of unknown compounds.
- Report the results of laboratory experiments in a laboratory notebook, performing quantitative calculations and interpreting results.
- Describe the electronic structure of the atom and draw the Lewis electron dot structures of organic molecules including resonance forms and formal charges where appropriate. Predict patterns of covalent and ionic bonding and draw and interpret condensed, structural and line angle formulas.
- Predict the hybridization and geometry of organic molecules based on their bonding and VSEPR theory applying the basic ideas of molecular orbital theory.
- Identify acids, bases, electrophiles and nucleophiles. Compare their strengths and predict their reactions.
- Identify and provide examples of the general classes of organic compounds: alkanes, alkenes, alkynes, alkyl halides, aromatic, alcohols, ethers, aldehydes, ketones, carboxylic acids, esters, nitriles, amides, and amines.
- Draw structures for and provide IUPAC names for alkanes, cycloalkanes, alkyl halides, alkenes, cycloalkenes, alkynes, and alcohols and discuss their structures, stability when appropriate, and predict physical properties such as melting point, boiling point and solubility. Provide common names when appropriate.
- Draw alkane and cycloalkane conformations, using Newman projections when appropriate, comparing energies and predicting stability.
- Classify carbons as primary, secondary, tertiary or quaternary. Classify alkyl halides and alcohols as primary, secondary or tertiary.
- Propose a mechanism, predict products and explain the steps for the free-radical halogenation of an alkane.
- Identify isomers, structural and stereoisomers, and explain the differences between them. Recognize chiral compounds, determine configurations of the stereocenter, and classify pairs of compounds as enantiomers, diasteromers, or a different class of isomer. Draw chiral compounds using perspective drawings and Fisher projections.
- Calculate specific rotation and use to determine optical purity and enantiomeric excess of mixtures.
- Predict the products, with proper stereochemistry, of substitution (SN1, SN2) and elimination (E1, E2) reactions involving alkyl halides, providing detailed reaction mechanisms and explain what factors determine the order of the reaction.
- Identify reactive intermediates, such as carbocations, radicals, carbanions, and carbenes and predict their relative stabilities. Determine the possible rearrangements of carbocations.
- Provide detailed reaction mechanisms for the syntheses of alkenes via the E2 mechanism and the acid catalyzed dehydration of alcohols and provide detailed reaction mechanisms and predict the products of reactions of alkenes, including electrophilic additions to and oxidation of alkenes.
- Provide detailed reaction mechanisms for the synthesis of alkynes via elimination reactions and predict the products and provide mechanisms for the reactions of alkynes via additions and oxidations.
- Provide detailed reaction mechanisms for the synthesis of alcohols using organometallic reagents and also reducing agents and provide detailed reactions mechanisms and predict the products of reactions of alcohols including oxidations, dehydrations including the Pinacol rearrangement, and the Williamson ether synthesis.