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Unformatted text preview: first conversion is shown below. The β-ketoester reacts with acrylonitrile to form the
alkylated product in 63% yield. This _________________ Reaction takes advantage of the β-ketoester ’s
acidity. The pKa of the β-ketoester is approximately ______. Draw the arrow-formalism for this reaction.
OE t O
H3C EtOH solvent O
CN 7. (10 points) Acrylonitrile is not a typical Michael reagent. Do you expect it to be more or less reactive than
an α,β-unsaturated ketone? One way to analyze such a question is to look at the pKa of the saturated ketone
and nitrile. Provide an approximate pKa value for each molecule and then briefly explain how this pKa value
aids in explaining the relative reactivity of the unsaturated molecules in a Michael Reaction.
CH3 H3C C N pKa An alternate though no less important way to explain the relative reactivities of acrylonitrile vs. an...
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- Spring '08