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
Related questions
Question
![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](/v2/_next/image?url=https%3A%2F%2Fcontent.bartleby.com%2Fqna-images%2Fquestion%2F41cb2808-6989-4a5d-a7c2-13f4e048bb40%2Fca36912e-85dc-495c-bf18-b696ec4fec2c%2Fwjcvc3k_processed.jpeg&w=3840&q=75)
Transcribed Image Text: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
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