11 Chemical Formula: C₂H₂O 12 cat. NaOMe B Chemical Formula: C14H1602 NaOMe MeOH 13 Chemical Formula: C14H14O

World of Chemistry, 3rd edition
3rd Edition
ISBN:9781133109655
Author:Steven S. Zumdahl, Susan L. Zumdahl, Donald J. DeCoste
Publisher:Steven S. Zumdahl, Susan L. Zumdahl, Donald J. DeCoste
Chapter3: Chemical Foundations: Elements, Atoms, And Ions
Section: Chapter Questions
Problem 50A
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When a mixture of ketone 11 and \alpha, \beta - unsaturated carbonyl 12 are exposed to substoichiometric amounts of NaOMe, product B is obtained selectively. Subsequent treatment of B with excess NaOMe leads to the exclusive formation of tricyclic product 13. (1) Suggest a structure for B and provide a reason for its selective formation. (ii) Provide a reaction mechanism for the formation of 13, which accounts for its selective formation.

11
Chemical Formula:
CgHgO
12
cat. NaOMe
B
Chemical Formula:
C14H1602
NaOMe
MeOH
13
Chemical Formula:
C14H110
Transcribed Image Text:11 Chemical Formula: CgHgO 12 cat. NaOMe B Chemical Formula: C14H1602 NaOMe MeOH 13 Chemical Formula: C14H110
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