CHEM 2061 - Organic Chemistry I

1. At the conclusion of the lecture portion of this course, learners will be able to…
   • Predict properties and reactivity of organic molecules using concepts of molecular structure, formal charge, and resonance.
   • Translate between compound names and representations of structure.
   • Analyze the relative energies of molecular structures.
   • Create and employ 3-dimensional structures to determine the constitutional and stereochemical isomeric relationships between molecules.
   • Identify various functional groups within complex molecules, correlate physical properties with functional group structure, and predict relevant reactions that each functional group will undergo.
   • Predict the products of acid-base, substitution, elimination, and addition reactions through the application of thermodynamic and kinetic principles.
   • Create logical synthetic strategies by combining reactions into practical multi-step sequences.
   • Propose reaction mechanisms using the curved-arrow formalism.
   • Develop a basic understanding of the theory of NMR spectroscopy and employ data from NMR spectroscopy to identify organic compounds.
2. At the conclusion of the laboratory portion of this course, learners will be able to…
   • Plan organic chemical reactions using proper reaction stoichiometry calculations.
   • Perform successful organic chemical reactions with hands-on use of reaction glassware and equipment, practicing proper laboratory technique to maximize product yield and purity.
   • Separate and purify chemical compounds.
   • Determine the identity of organic samples through physical and spectroscopic methods.
   • Determine the qualitative and quantitative purity of organic samples through physical and spectroscopic methods.
   • Demonstrate responsible laboratory safety and waste handling practices including the use of proper fume hoods or fume extraction for chemicals that emit hazardous vapors.
   • Communicate the procedure, results, and relative success of an experiment with respect to the experimental objectives in the form of a laboratory notebook, written reports, or a verbal presentation.

1. Major Areas of Lecture Content
   • Structure and bonding including Lewis structures, formal charges, resonance, polarity, molecular geometry, intermolecular forces, atomic, molecular, and hybrid orbitals, and recognizing functional groups.
   • Acids and bases including Bronsted-Lowry and Lewis theories, relative acid and base strengths, structural effects, and equilibria.
   • Alkanes and cycloalkanes including nomenclature, isomerism, physical properties, structure, and conformations.
   • Reaction energetics including kinetics, rate equations, enthalpy, equilibrium, equilibrium constants, free energy, transition states, reaction energy diagrams, reactive intermediates, mechanisms, and curved arrow notation.
   • Stereochemistry including chirality, optical activity, absolute configuration, enantiomers, diastereomers, and meso compounds.
   • Nucleophilic substitution and elimination reactions of alkyl halides including nucleophilicity, solvent effects, leaving groups, substrate effects, reaction order, stereochemistry, and determination of the major product in competing pathways.
   • Alkenes including structure, nomenclature, isomers, synthesis by elimination and dehydration, and reactions including hydration, hydroboration/oxidation, halogen addition, hydrogenation, ozonolysis, dihydroxylation, epoxidation, and polymerization.
   • Alkynes including structure and nomenclature, acidity, and reactions including electrophilic addition, oxidation, and reduction.
   • Nuclear Magnetic Resonance (NMR) spectroscopy including theory, chemical shift, chemical equivalence, integration, spin-spin splitting, and structure elucidation.
   • Organohalides including structure, properties and nomenclature, preparation of organohalides through radical mechanisms, and organometallic coupling reactions using Grignard and Gilman reagents.
   • Introduction to short multistep synthesis sequences.
2. Major Areas of Laboratory Content
   • Reaction Types and Techniques
     • Heating and cooling
     • Reflux
     • Microscale reactions
     • Acid-base reactions
     • Substitution reactions
     • Condensation reactions
     • Polymerization
     • Green chemistry
   • Separation and Purification Techniques
     • Liquid-liquid extraction
     • Simple distillation
     • Fractional distillation
     • Use of drying agents
     • Solvent evaporation
     • Column chromatography
     • Vacuum and gravity filtration
     • Recrystallization
   • Analytical Techniques
     • Thin-layer chromatography
     • Melting point analysis
     • Refractometry
     • Polarimetry
     • Gas chromatography
     • IR spectroscopy