The Scientific Literatre - University of Michigan

The Scientific Literatre - University of Michigan

The Scientific Literature Honors Cup 2005 1/13/05 General 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/~chemh215/CHE M216/216Hhome.htm NMR The 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 lab The 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 References Goals 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 characterization Interesting 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 OCH3 O O O O C13H27 O C13H27 O

O 5-allyl-1-methoxy-2,3 (methylenedioxy)benzene (nutmeg) O trimyristin C13H27 55.555g 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). Overall Reaction Scheme : A 3-Step Synthesis O HO N H - yield 36-61% *assume average 50% for experimental data 1. ethanol/NaOH O

O 2. CH3CH2i/reflux (II) (I) phenacetin acetominophen yield approximately 100% O NH3 Cl

O 1. solid NaCO3 O N H 2. CH3COOH/urea/reflux (III) p-phenetidine hydrochloride salt -yield 70-90% *assuming average 80%

for procedure (IV) dulcin NH2 Where do I get ideas? Medicine cabinet Internet

Flip through journals Fragrances, flavors Labels and ingredients Forbidden Fruits Aspirin Dulcin Mysteric acid Once 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 PCs) Characterization Synthesis

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