Massachusetts Institute of Technology

Organic Chemistry 5.13

September 29, 2003

Prof. Timothy F. Jamison

Assignment and Study Guide for Unit II

The Chemistry of Ethers, Epoxides, and Sulfides

Some Important Epoxides and Sulfur-containing Molecules

O
O

H3C
O CH3
S
HO
S
diethyl ether
OH allicin

organic solvent,

19th-century anesthetic benzo[a]pyrene-7,8-diol 9-10 epoxide odor of garlic

potent carcinogen

CO2H N
O N NH2
H2N S
CH3 N N
HO OH
S-adenosylmethionine O
squalene oxide
cellular methylating agent precursor to natural steroids
("nature's methyl iodide")

Reading Assignment Wade Chapter 14 (pp. 600-637)

Problem Set 2: Text Problems in Chapter 14: 5, 7-10, 14-19, 20 (Historical note: The majority of
the research that was recognized with the 2001 Nobel Prize in Chemistry to Prof.
K. Barry Sharpless was performed at MIT.), 21, 23-28, 30, 33, 35-42, 44-47.

Due Fri., October 3, 4 p.m.