
Chemistry
10th Edition
ISBN: 9781305957404
Author: Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Publisher: Cengage Learning
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Transcribed Image Text:4. An enzyme (acetoacetate decarboxylase) catalyzes the decarboxylation of acetoacetate. The mechanism has
been studied extensively; concluding that the key bond-breaking step involves an enamine as a leaving
group.
Draw a curved arrow mechanism in the boxes below. Label the "iminium” and then "enamine" and
then "iminium" as three consecutive intermediates in the mechanism. Note that the acid is stoichiometric
PLUS catalytic. (Hint: acid-base involving oxygen should be drawn concerted with other steps)
Enz
(cat.)
NH2
EnzAH
EnzAH (cat.)
O=U=0
Θ
EnzA
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