Organic Chemistry III

Homework Problems

September 20, 2000

Provide a reasonable mechanism, including proper use of curved arrow formalism, that shows how the transformations below and on the reverse of this sheet occur. Show all products and byproducts.

TMS

OH
Tf2O, CH2Cl2 2,6-lutidine, -78 oC

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I AIBN
CF3CF2CF2CF2I

SiMe3 75 C, 8h

CF3CF2CF2CF2

SiMe3

n-Bu4NF DMSO or THF 65 oC, 5 min

CF3CF2CF2CF2

added during class:

CHCl3, NaOH

R-NH2

_ + R N C