Chem 51LC Labs

Week 1: Clove Oil Steam Distillation

        Eugenol distilled from cloves.  Purity assessed by TLC and possibly 1H NMR. Introduction to distillation. Review of vapor pressure and boiling point.

Week 2: Electrophilic Aromatic Substitution

        Relative reactivities determined by bromination of aromatic rings bearing various substituents.

Weeks 3-4: Wittig

        Each lab section is given a variable to explore (Wititg salt, aldehyde, or base) and a list of available chemicals.  Focus is on how variable might affect E/Z selectivity of products.  As a section, with TA guidance, students design their own experiment.  Students run proposed reactions during second week of experiment.  1H NMR analysis of all products within a section shared to all students in that section.  Students identify any trend present and address how this trend corresponds with their initial hypothesis.

Weeks 4-6: Oxidation and Reduction

        Oxidation of 4-t-butylcyclohexanol to 4-t-butylcyclohexanone.  Reductions of ketone using sodium borohydride and Meerwein-Pondorff-Verley conditions.  NMR spectroscopy of resulting product mixtures.  Spectra for product mixture resulting from reduction using L-selectride provided.  Analysis requires explaining the differences in product mixtures under three different sets of reduction conditions. Help with analysis is provided in video and in person during lab lecture.

Week 7: Determining Absolute Configuration Using CEC Method

        Experiment developed from work in Rychnovsky lab.  Students qualitatively and quantitatively determine which reaction proceeds faster in matched and mismatched case of acetylation of an alcohol with a chiral catalyst and determine absolute configuration of unknown chiral alcohol. Review of assigning R/S and optical rotation included.

Week 8: Aldol Condensation

Double aldol condensation with unknown aldehyde and ketone. Differentiate aldehyde and ketone by IR.  Determine structures of unknowns by first determining structure of product by 1H and 13C NMR.

        

Week 9: No Labs - Memorial Day Holiday
        

Week 10: Lab Practical (during normal lab time)

Summer Session Notes

Summer session classes meet in lab two times per week. Please see calendar for exact dates. Calendar is typically updated during Spring quarter.

Rev 3/1/18