EtO₂C CO₂Et I Br K EtO₂C CO₂Et H

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 50AP
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ANSWER THE LAST PART (V) SHOWING STEP BY STEP CURLY ARROW MECHANISM PLEASE 

Jasmone
J
EtO₂C CO₂Et
I
Br
K
F
EtO₂C CO₂Et
H
(iii) During the conversion of G into F an undesired, isomeric, cyclopentenone also forms. Draw this
compound and explain briefly how it arises.
(iv) In a recent publication the conversion of diester H into diketone G was detailed. In this work H
was prepared from diethyl malonate I, methyl vinyl ketone J and bromide K. Disconnect H,
showing the relevant synthons in order to arrive at the synthetic equivalents (I to K) provided.
(v) According to your answer to section (iv), and including curly arrow reaction mechanisms, show
how H can be prepared from I, J and K.
Transcribed Image Text:Jasmone J EtO₂C CO₂Et I Br K F EtO₂C CO₂Et H (iii) During the conversion of G into F an undesired, isomeric, cyclopentenone also forms. Draw this compound and explain briefly how it arises. (iv) In a recent publication the conversion of diester H into diketone G was detailed. In this work H was prepared from diethyl malonate I, methyl vinyl ketone J and bromide K. Disconnect H, showing the relevant synthons in order to arrive at the synthetic equivalents (I to K) provided. (v) According to your answer to section (iv), and including curly arrow reaction mechanisms, show how H can be prepared from I, J and K.
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