Propose a mechanism to account for the following reaction. Hint: Start by removing the most acidic proton and work your way from there. The triphenylphosphonium group is electron withdrawing. A four step mechanism is sufficient COOET PPH3 NaH + COOET COOE1 COOET

Organic Chemistry
9th Edition
ISBN:9781305080485
Author:John E. McMurry
Publisher:John E. McMurry
Chapter9: Alkynes: An Introduction To Organic Synthesis
Section9.SE: Something Extra
Problem 21MP
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Propose a mechanism to account for the following reaction. Hint: Start by removing the most acidic proton and work your
way from there. The triphenylphosphonium group is electron withdrawing. A four step mechanism is sufficient
COOET
coOEt
PP 3
NaH
COOET
СООEt
COOET
Transcribed Image Text:Propose a mechanism to account for the following reaction. Hint: Start by removing the most acidic proton and work your way from there. The triphenylphosphonium group is electron withdrawing. A four step mechanism is sufficient COOET coOEt PP 3 NaH COOET СООEt COOET
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