30. The reaction shown will form an enol intermediate prior to tautomerization to the final product. a. Draw the final product. (4 pts) 1.9-BBN 2. H₂O₂, NaOH b. Draw the enol intermediate and show the mechanism of the base catalyzed tautomerization to final product. (8 pts) c. How would the mechanism for the tautomerization reaction change if it was acid catalyzed instead of base catalyzed? You may describe this in 1-2 sentences or draw the new mechanism to show the difference. (6 pts) d. In a tautomerization reaction, what determines if you produce a primary or secondary product? You can use a brief description or generic structures to illustrate your reasoning. (4 pts) Page 17

Chemistry
10th Edition
ISBN:9781305957404
Author:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Publisher:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Chapter1: Chemical Foundations
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30. The reaction shown will form an enol intermediate prior to tautomerization to the final
product.
a. Draw the final product. (4 pts)
1.9-BBN
2. H₂O₂, NaOH
b. Draw the enol intermediate and show the mechanism of the base catalyzed
tautomerization to final product. (8 pts)
c. How would the mechanism for the tautomerization reaction change if it was acid
catalyzed instead of base catalyzed? You may describe this in 1-2 sentences or
draw the new mechanism to show the difference. (6 pts)
d. In a tautomerization reaction, what determines if you produce a primary or
secondary product? You can use a brief description or generic structures to
illustrate your reasoning. (4 pts)
Page 17
Transcribed Image Text:30. The reaction shown will form an enol intermediate prior to tautomerization to the final product. a. Draw the final product. (4 pts) 1.9-BBN 2. H₂O₂, NaOH b. Draw the enol intermediate and show the mechanism of the base catalyzed tautomerization to final product. (8 pts) c. How would the mechanism for the tautomerization reaction change if it was acid catalyzed instead of base catalyzed? You may describe this in 1-2 sentences or draw the new mechanism to show the difference. (6 pts) d. In a tautomerization reaction, what determines if you produce a primary or secondary product? You can use a brief description or generic structures to illustrate your reasoning. (4 pts) Page 17
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