Diethyl malonate (CH3CH₂O₂C-CH₂-CO₂CH₂CH3) is treated with NaOEt followed by Br-CH₂CH₂CH₂CH3. The resulting product is heated in acid. a) Draw the structure of the final product. b) Use curved arrow formalism to draw the mechanism of the decarboxylation step (ONLY!) in the reaction sequence described above.

Organic Chemistry: A Guided Inquiry
2nd Edition
ISBN:9780618974122
Author:Andrei Straumanis
Publisher:Andrei Straumanis
Chapter11: Addition To Alkynes
Section: Chapter Questions
Problem 1E
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Diethyl malonate (CH3CH₂O₂C-CH2-CO₂CH₂CH3) is treated with NaOEt followed by Br-CH₂CH₂CH₂CH3. The
resulting product is heated in acid.
a) Draw the structure of the final product.
b) Use curved arrow formalism to draw the mechanism of the decarboxylation step (ONLY!) in the reaction sequence
described above.
Transcribed Image Text:Diethyl malonate (CH3CH₂O₂C-CH2-CO₂CH₂CH3) is treated with NaOEt followed by Br-CH₂CH₂CH₂CH3. The resulting product is heated in acid. a) Draw the structure of the final product. b) Use curved arrow formalism to draw the mechanism of the decarboxylation step (ONLY!) in the reaction sequence described above.
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