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/CHEM216/216Hhome.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

O

C13H27O O C13H27

C13H27

O

O O

O

O

OCH3

5-allyl-1-methoxy-2,3 (methylenedioxy)benzene(nutmeg)

trimyristin

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)..

HO NH

O

O

O

1. ethanol/NaOH

2. CH3CH2i/reflux

NH3O Cl 1. solid NaCO3

2. CH3COOH/urea/reflux

NH

O NH2

O

(I) (II)

(III) (IV)

acetominophen phenacetin

p-phenetidine hydrochloride salt dulcin

- yield 36-61%*assume average 50% for experimental data

yield approximately 100%

-yield 70-90%*assuming average 80% for procedure

Overall Reaction Scheme : A 3-Step Synthesis

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