Lehman College Department of Chemistry City University of New York

Spring 2011 CHE 235: Organic Chemistry Laboratory II Text: K. L. Williamson; “Macroscale and Microscale Organic Experiments,” Houghton Mifflin Publishing Company, 5th Edition, 2007. ISBN10: 0-618-59067-6 Laboratory Notebook: Available in the bookstore. For each experiment you must read the whole introduction to the chapter.

SAFETY GLASSES MUST BE WORN IN THE LABORATORY AT ALL TIMES!

Experiments and Assigned Problems 1. Check In. Discussion of writing “The Laboratory Notebook.” special handouts, Discussion of ”Laboratory Safety and Waste Disposal.”For writing the notebook see separate handout and Online Study Center pp.22 and xi of your lab book. 2. 55 (p716) The Borohydride Reduction of a Ketone, Sodium Borohydride reduction of Benzil (Macroscale, p718) Problems: 1 and 2. 3. 41 ( p 569) Acetylsalicylic acid (Aspirin) Experiment: Synthesis of aspirin using three different catalyst. ( Macroscale, p 573). Omit boron trifluoride etherate. Problems: 1,2 4. 48 (p 661) Diels-Alder Reaction: (1) Experiment 1; Cracking of Dicyclopentadiene (Macroscale, 667).(2)Experiment 2; Synthesis of cis-Norbornene-5,6-endo-Dicarboxylicanhydride (Microscale, p 668) Problems, 2,3, IR 48.6, 48.8. 5. 22 (p 375) Oxidation: Cyclohexanol to Cyclohexanone: Experiment: 4 (p 383-4). Please use half the amount that is used in the experiment. Continue to completion following “The Isolation of Cyclohexanone from the Steam Distilate.” (p.380) Problems: Fig 22.7 and fig 22.8 Assign IR peaks where applicable. 6. 29 (p.436) Friedel-Crafts Alkylation: Experiment 29.4,1,4-di-t-butyl-2,5-dimethoxybenzene (Microscale, p 443). Follow the procedure only to the 7th line on page 444 to ....thouroughly with water. Problems: 5 and 6. 7. 12 (p 251) Nuclear Magnetic Resonance Spectroscopy (NMR) : Write only one page introduction in your lab notebook. Instructor discretion for the method of presentation. 8. 25 (p 404) (1) Catalytic Hydrogenation: Experiment: 25.4 (p 413) Transfer Hydrogenation of olive oil (Microscale. 40 (p 554) p. 415) and Isolation of Products. p. 516 (2) Esterification and Hydrolysis: Experiment: 40.5, Hydrolysis (Saponification): The preparation of soap (Microscale, p565) No problems assigned. 9. 38 (p 528) Grignard Synthesis, , Experiments: (1) 38.1, Phenylmagnesium Bromide (Microscale, p533); (2)38.2, Triphenylmethanol (p 535). Problems: handouts. 10. 63 (p 766) Carbohydrates and Sweeteners, Experiments: (1) 63.1 Molisch test (p 770); (2) 63.2, Red Tetrazolium (RT) test (p 770); (3) 63.4 Bial’s test (p 771). No problems assigned. 11. 14(p. 293) Qualitative Instrumental Organic Analysis, Chapter 14 (Pages 301-305) 12. Special instructions by the instructor. No problems assigned. 13. 37 (p 521) Dibenzalacetone by the Aldol Condensation, Experiment: Synthesis of dibenzalacatone (Macroscale, p 524). Problems: 1,3-5 14 Check out, Quiz Grading: Will be discussed by your instructor. “ The Beautiful Thing About Learning Is That No One Can Take It Away From You.” B. B.