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Massachusetts Institute of Technology

5.13: Organic Chemistry II Fall 2003, S. Tabacco


Optional Problem Solving Session
Monday, December 1st, 121PM

1. Please provide a detailed mechanism for each of the following transformations.


Do not concern yourself with stereochemistry.

a) 1. LDA O
O 2. O

Me OMe Me
3. H2O
OMe
MeO CO2Me

b) Me
Me
H3O+

O HO

c) AcO
AcO
H+ O
O

d) H
O
O CO2Me Lewis Acid

(LA) H
CO2Me
CO2Me MeO2C

These mechanisms are fairly complicated. In other words, if you can do these, you will be
fine on the exam! Working through these problems will help you to develop a good strategy
for tackling simpler problems in a reasonable time frame. It might help you to follow some of
the following steps to get started.

1. Number your carbons. (Which carbon ends up where?)

2. Make a list of the bonds that are broken and formed in the reaction.

3. If you can't decide where to begin, start by working backwards.

4. Look for familiar reactions, rearrangements, etc.

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