Introduction to General, Organic and Biochemistry
11th Edition
ISBN:9781285869759
Author:Frederick A. Bettelheim, William H. Brown, Mary K. Campbell, Shawn O. Farrell, Omar Torres
Publisher:Frederick A. Bettelheim, William H. Brown, Mary K. Campbell, Shawn O. Farrell, Omar Torres
Chapter10: Organic Chemistry
Section: Chapter Questions
Problem 10.49P
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Question
Provide a mechanism for the intramolecular nucleophilic addition and elimination reaction shown here by providing the missing structures (including the final product) and curved arrows. The reaction resembles a Dieckmann condensation, except instead of two esters, the molecule contains an ester and a ketone. The ketone is more acidic and will be the nucleophile. Your structures should include all nonzero formal charges and lone pairs of electrons. When drawing the enolate place the negative charge on the carbon not the oxygen.
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