Problem Set 4

Due in class Friday, November 7.

A. Problems from text:

4.2, 4.3 (any 6 of the 13); 4.13 a,c.

B.  Additional problems.

1.  Use reaction energy diagrams to illustrate whether (and why) the following reactions will speed up or slow down when moved from nonpolar to polar solvents.

2.  The following rearrangement has been observed.

a.  Propose a mechanism.  You should specifically justify the stability of any intermediates compared to other (unobserved) possibilities.

b.  Provide a bonding description for the key intermediate responsible for the carbon skeleton reorganization that explains why the rearrangement occurs.

c.  Assuming the reactant could be prepared as a single enantiomer, is the process stereospecific?  Why or why not?

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Last updated 9/18/2008