The Scientific LiteratureGeneral 216 AnnouncementsThe Honors CupThe ProposalGoals for your ProposalInteresting Molecule or ProcessWhat is NOT a Synthetic Transformation?ExtractionPowerPoint PresentationWhere do I get ideas?Forbidden FruitsOnce you have an idea….The Scientific LiteratureHonors Cup 20051/13/05General 216 Announcements•Office Hours: 3:30-5:00 2404 Thursdays•GSI “office hours”•Post experiment 1 details ~5pm on Friday at: http://www.umich.edu/~che mh215/CHEM216/21 6Hhome.htm•NMRThe Honors Cup •Proposal –Check (Fri 1/28 10 am e-mail to Dr. Gottfried) –Final Version (Monday 2/7 10am e-mail to Dr. Gottfried•Peer Review–Week of 2/7; review all proposals in section using rubric provided by 10 am Friday 2/11•Synthesis–Last six weeks of labThe Proposal•Target: what is it and why is it (or the series of transformations) important•Overall Scheme•For each step–A ChemDraw picture of the transformation–An experimental –Any green or safety issues•Budget•ReferencesGoals for your Proposal•Interesting process or molecule that you would like to carry out•3 synthetic transformations•216H doable experimentals–Time–Scale–Equipment and technique•0.5 g final product•Doable characterizationInteresting Molecule or Process•Forward–What synthetic transformations are you interested in?–What processes are most interesting?–Do you want to use a green reaction?•Retro Synthesis–What molecule are you interested in making?–Make a functional group like that of a larger molecule.What is NOT a Synthetic Transformation?•A synthetic transformation changes one functional group to another.•Remember you need to isolate and characterize the product of each step.•Reaction work-ups and extractions are not synthetic transformations.Extraction OC13H27O O C13H27C13H27OOOOOOCH35-allyl-1-methoxy-2,3 (methylenedioxy)benzene(nutmeg)trimyristin55.555g of ground nutmeg is to be heated under reflux for 30 minutes with 138.888mL of diethyl ether (6). The mixture should be cooled to room temperature and the solid decanted. Wash with 55.555mL of diethyl ether, and distill the liquid to recover the solvent (7). 11.666g of solid yellow residue will appear. Recrystallization from ethanol is possible to recover 2.833g of trimyristin (a white solid, 5% yield based on starting nutmeg) with MP 56-58 oC and Rf .5 on TLC (Thin Layer Chromatography) with Hexane solvent system (1)..HO NHOOO1. ethanol/NaOH2. CH3CH2i/refluxNH3OCl1. solid NaCO32. CH3COOH/urea/refluxNHO NH2O(I)(II)( III)( IV)acetominophenphenacetinp-phenetidine hydrochloride salt dulcin- yield 36-61%*assume average 50% for experimental datayield approximately 100%-yield 70-90%*assuming average 80% for procedureOverall Reaction Scheme : A 3-Step SynthesisWhere do I get ideas?•Medicine cabinet•Internet•Flip through journals•Fragrances, flavors•Labels and ingredientsForbidden Fruits•Aspirin•Dulcin•Mysteric acidOnce you have an idea….•www.lib.umich.edu–Electronic Journals and Newspapers–Networked Electronic Resources•SciFinder (SLC PCs and Macs)–Author–Transformation –Molecule (synthesis, etc.)•Beilstein (SLC
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