CALIFORNIA STATE POLYTECHNIC UNIVERSITY, POMONA Organic Chemistry Laboratory CHM 318L Schedule – Winter 2016 CHM 318L Prerequisites: CHM 317L Concurrent or Prerequisite: CHM 315* Date Experiment/Activity Experimental Procedure and Required Reading 1 1/4 Check-in. Introduction to KLW Chapters on “Infrared Spectroscopy” and “Nuclear NMR Spectroscopy Magnetic Resonance Spectroscopy” (KLW = Williamson text) Wade Ch. 12 (IR) and Wade Ch. 13 (NMR) 2 1/11 NMR spectroscopy (cont’d) 3 1/18 Holiday 4 1/25 “Alkenes from Alcohols: KLW Macroscale #2, 20 g scale, skip toluene chaser Cyclohexene from Wade Ch. 7-10 “Alkene Synthesis by Dehydration of Alcohols” Cyclohexanol” 5 2/1 Addition/Elimination KLW Synthesis of “meso-Stilbene Dibromide” Microscale #2, “Synthesis of an Alkyne run reaction at four times scale (200 mg stillbene); and “Synthesis from an Alkene: of Diphenylacetylene” Microscale #3, use product isolated from Bromination and Microscale #2 Dehydrobromination” Wade Ch. 8-8 “Addition of Halogens to Alkenes” and Wade Ch 7-9 “Alkene Synthesis by (E2) Elimination of Alkyl Halides” 6 2/8 “Oxidation: Cyclohexanol KLW Macroscale #4 at 1/3 the amounts (2.7 mL cyclohexanol), to Cyclohexanone” includes Macroscale #3 “Isolation of Cyclohexanone from the Steam Distillate” (also review KLW chapter on Steam Distillation) Wade Ch. 11-2 “Oxidation of Alcohols” 7 2/15 “Sodium Borohydride KLW run reaction at four times scale (1.2 g ketone) Reduction of NOTE: sodium borohydride contains four equivalents of hydride 2-Methylcyclohexanone” (i.e., 1 mole NaBH4 = 4 moles hydride) Wade Ch. 10-11 & 18-20 “Reductions of Ketones & Aldehydes” 8 2/22 “Grignard Synthesis of KLW preparation of “Phenylmagnesium Bromide” Macroscale Triphenylmethanol” #4, run reaction at 1/2 scale and then use the entire amount in the next step, “Triphenylmethanol from Benzophenone” #6 and “Completion of Grignard Reaction,” #7 Wade Ch. 10-8 “Organometallic Reagents for Alcohol Synthesis” 9 2/29! Grignard Synthesis (cont’d) 10 3/7 Check-Out, Lab final *Students withdrawing from the associated lecture course (CHM 315) at any time during the quarter are also required to withdraw from lab. • Lab Textbook: Macroscale and Microscale - Selected Organic Experiments, Williamson, K.L., Heath & Co., ISBN 0-618-82428-6. Any edition of Williamson can be used. Please refer to the Experiment Titles and use the book’s Index to find the appropriate chapter/experiment and the assigned reading. • Lecture Textbook: Organic Chemistry, Wade, Prentice Hall, 8th Edition, 2013 (any edition can be used) • Also recommended: The Organic Chem Lab Survival Manual, Zubrick, J.W., Wiley, any edition. (You used this book in CHM 317L.) University Holidays: Monday, 1/18 and Friday, 2/12 .