Come up with a detailed mechanism for the following cyclization that also includes all resonance strictures for any intermediates that form. Also, explain why the alkyl bromide portion of the molecule remains intact in the product even though the reaction conditions are strongly basic/nucleophilic. Br Br NaOMe Me Me Me Me MeOH MeO2C 0 °C MeO₂C

Organic Chemistry: A Guided Inquiry
2nd Edition
ISBN:9780618974122
Author:Andrei Straumanis
Publisher:Andrei Straumanis
Chapter26: Aldol And Claisen Reactions
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Problem 26E
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Come up with a detailed mechanism for the following cyclization that also includes all
resonance strictures for any intermediates that form. Also, explain why the alkyl bromide
portion of the molecule remains intact in the product even though the reaction conditions are
strongly basic/nucleophilic.
Br
Br
NaOMe
Me
Me
Me
Me
MeOH
MeO2C
0 °C
MeO₂C
Transcribed Image Text:Come up with a detailed mechanism for the following cyclization that also includes all resonance strictures for any intermediates that form. Also, explain why the alkyl bromide portion of the molecule remains intact in the product even though the reaction conditions are strongly basic/nucleophilic. Br Br NaOMe Me Me Me Me MeOH MeO2C 0 °C MeO₂C
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