CHEM 2062 - Organic Chemistry II

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.
   • 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 each functional group will undergo.
   • Predict the products of oxidation, reduction, aromatic substitution, nucleophilic acyl addition, nucleophilic acyl substitution, and alpha carbon (enol and enolate) 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.
   • Employ data from NMR, IR, and UV-VIS spectroscopy and mass spectrometry to identify compounds and demonstrate an understanding of how each of these analytical techniques work.
   • Identify structures and functions of macromolecules.
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.
   • Model the scientific method by performing inquiry- or research-based laboratory experiments or projects in which the student makes decisions regarding experimental design and execution.
   • 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
   • UV-visible spectroscopy including energy level transitions, chromophores, and wavelength of maximum absorption.
   • Infrared (IR) Spectroscopy including theory, stretching frequencies, and functional group identification.
   • Mass spectrometry including electron ionization, the molecular ion, isotope analysis, fragmentation pathways, structure elucidation, and Matrix-Assisted Laser Desorption Ionization Mass Spectrometry (MALDI-MS).
   • Alcohols and phenols including structure, properties and nomenclature, preparation of alcohols and alkoxides, reactions including alkyl halide preparation, Williamson ether synthesis, epoxide ring opening, and oxidation.
   • Aldehydes and ketones including structure, properties, and nomenclature; synthesis by oxidation of alcohols; reactions including reduction, organometallic addition, acetals and ketals, addition of nitrogen nucleophiles, and the Wittig reaction.
   • Carboxylic acids and derivatives including structure, properties, and nomenclature; synthesis by oxidation and reaction with organometallic reagents; reactions including conversion to acid chlorides and anhydrides, hydrolysis, esterification, amide formation, soaps, fats, and oils.
   • Chemistry of aromatic compounds including structure, properties, and nomenclature; aromaticity and Huckel’s rule; electrophilic aromatic substitution reactions, nucleophilic aromatic substitution, Friedel-Crafts alkylation and acylation.
   • Enolate chemistry including acidity of alpha hydrogens, enolate formation, keto-enol tautomerization, reactions of enolate ions including alpha-halogenation and alkylation, racemization, aldol condensation, Claisen condensation, decarboxylation, Michael addition and other conjugate additions.
   • Polyenes including conjugation and stability, molecular orbital theory, 1,2- vs. 1,4- addition reactions, and Diels-Alder reaction.
   • Amines including structure, properties, and nomenclature; synthesis from alkyl halides and by reduction; reactions including nitrosation and diazonium salt formation and reactions.
   • Introduction to carbohydrates including stereochemistry and nomenclature of monosaccharides, Fischer projections, D- and L- configurations, cyclic hemiacetal forms, and anomeric effect.
   • Introduction to peptides.
   • Multistep synthesis including retrosynthetic analysis and protecting groups.
2. Major Areas of Laboratory Content
   • Reaction Types and Techniques
     • Heating and cooling
     • Reflux
     • Moisture- or air-sensitive reactions
     • Acid-base reactions
     • Addition reactions
     • Substitution reactions
     • Elimination reactions
     • Condensation reactions
     • Oxidation/reduction
     • Carbon-carbon bond formation
   • Separation and Purification Techniques
     • Liquid-liquid extraction
     • Use of drying agents
     • Solvent evaporation
     • Vacuum and gravity filtration
     • Recrystallization
   • Analytical Techniques
     • IR spectroscopy
     • 1H and 13C NMR spectroscopy