(i) Identify a-protons in compound H, estimate their pKa values and draw the structure for the two different enolates that could form under basic conditions. Explain why one enolate is more stable than the other. Eto (ii) Show the structure of mono-alkylation product J and give a mechanism for its formation. Explain why NaOMe would not be a suitable base for this reaction. OEt mechanisms. Br NaOEt H Ph OEt (1) NaOH(aq) (2) Acidify HO K Ph (iii) In the subsequent step adduct J is converted into carboxylic acid K under the conditions given. Explain this decarboxylation process that occurs when heating using curly arrow

(i) Identify a-protons in compound H, estimate their pKa values and draw the structure for the two different enolates that could form under basic conditions. Explain why one enolate is more stable than the other. Eto (ii) Show the structure of mono-alkylation product J and give a mechanism for its formation. Explain why NaOMe would not be a suitable base for this reaction. OEt mechanisms. Br NaOEt H Ph OEt (1) NaOH(aq) (2) Acidify HO K Ph (iii) In the subsequent step adduct J is converted into carboxylic acid K under the conditions given. Explain this decarboxylation process that occurs when heating using curly arrow

Organic Chemistry

8th Edition

ISBN:9781305580350

Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote

Publisher:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote

Chapter21: Benzene And The Concept Of Aromaticity

Section: Chapter Questions

Problem 21.64P: Following is a synthesis for toremifene, a nonsteroidal estrogen antagonist whose structure is...

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