Co2 o o br oh o o ho br oh h o o br o mgo o o mgbr c

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Unformatted text preview: roup
is
 DMF 
 placed
antiperiplanar
to
the
nucleophile
approach.

 O This
allows
a
good
interaction
to
form
between
the
 
 insipient
Nu‐C
bond
and
the
σ*
orbital
of
the
C‐Cl
bond.

 Et 
 A
similar
interaction
occurs
when
the
ethyl
group
is
at
 
 Cl the
antiperiplanar
position,
however
the
C‐Cl
σ*
is
 
 significantly
lower
in
energy
than
the
C‐C
σ*,
which
 O NC OH 
 makes
his
σσ*
interaction
more
favorable
for
C‐Cl.
 KCN O DMF 
 
 Cl Cl Et H 
 CN Problem
 #3.)
 Provide
 a
 mechanism
 for
 the
 following
 transformation.
 
 Hint:
 you
 should
 invoke
an
ylide
at
some
point
in
your
mechanism.
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 Problem
 #4.)
 Using
 the
 building
 blocks
 b...
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This note was uploaded on 01/24/2014 for the course CHEM 436 taught by Professor White during the Spring '08 term at University of Illinois, Urbana Champaign.

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