Problem 8.1 a) Choose the most atom economical protecting group (PG) for the alcohol that would be stable to the strong basic Horner - Emmons reagent in the reaction with the aldehyde to make the alkene given below (picture attached). b) What is the approximate pKa of a primary alcohol? Estimate the pKa of the Horner - Emmons conjugate acid (H instead of Li) based on the pKa of a simple beta - diester. c) Draw an acid-base reaction between an alcohol and a beta diester base. Which side would the equilibrium be skewed towards? By how many orders of magnitude? d) How could you avoid the need for a protecting group in this reaction? PG.O ནཱནཱགཱ, PG. EtO-P Eto OEt H OEt + O=P EtO-P Eto +7-0

Problem 8.1 a) Choose the most atom economical protecting group (PG) for the alcohol that would be stable to the strong basic Horner - Emmons reagent in the reaction with the aldehyde to make the alkene given below (picture attached). b) What is the approximate pKa of a primary alcohol? Estimate the pKa of the Horner - Emmons conjugate acid (H instead of Li) based on the pKa of a simple beta - diester. c) Draw an acid-base reaction between an alcohol and a beta diester base. Which side would the equilibrium be skewed towards? By how many orders of magnitude? d) How could you avoid the need for a protecting group in this reaction? PG.O ནཱནཱགཱ, PG. EtO-P Eto OEt H OEt + O=P EtO-P Eto +7-0

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

Chapter8: Haloalkanes, Halogenation, And Radical Reactions

Section: Chapter Questions

Problem 8.32P

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