OVERALL REACTION Michael reaction NaOCH, CH,OH H3CO OCH3 H,CO. OCH3 mesityl oxide dimethyl malonate Intramolecular NaOCH, CH,OH Claisen Condensation Decarboxylation or Dieckmann Cyclization heat 1) NaOH но, H3CO 2) HCI Saponification or base-catalyzed Ester Hydrolysis dimedone

Organic Chemistry
9th Edition
ISBN:9781305080485
Author:John E. McMurry
Publisher:John E. McMurry
Chapter23: Carbonyl Condensation Reactions
Section23.SE: Something Extra
Problem 61AP
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Show the stepwise mechanism. Show all lone pairs and formal charges

OVERALL REACTION
Michael reaction
NaOCH3
CH,OH
H3CO
OCH3
H3CO.
OCH3
mesityl oxide
dimethyl malonate
Intramolecular
NaOCH3
CH,OH
Claisen
Condensation
Decarboxylation
or
Dieckmann
Cyclization
heat
1) NaOH
но.
H3CO.
2) HCI
Saponification or
base-catalyzed
Ester Hydrolysis
dimedone
Transcribed Image Text:OVERALL REACTION Michael reaction NaOCH3 CH,OH H3CO OCH3 H3CO. OCH3 mesityl oxide dimethyl malonate Intramolecular NaOCH3 CH,OH Claisen Condensation Decarboxylation or Dieckmann Cyclization heat 1) NaOH но. H3CO. 2) HCI Saponification or base-catalyzed Ester Hydrolysis dimedone
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