Answered: several steps NaOEt (2 equiv) но- OEt…

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several steps NaOEt (2 equiv) но- OEt Bг Br он он illudin-S

Chemistry: Matter and Change

1st Edition

ISBN:9780078746376

Author:Dinah Zike, Laurel Dingrando, Nicholas Hainen, Cheryl Wistrom

Publisher:Dinah Zike, Laurel Dingrando, Nicholas Hainen, Cheryl Wistrom

Chapter6: The Periodic Table And Periodic Law

Section6.2: Classification Of The Elements

Problem 15SSC

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Concept explainers

Reactions at the Alpha Carbon Atom

The position next to the ketone or aldehyde functional group is termed as alpha position and the reaction which occurs at alpha position is called alpha substitution reaction. In an alpha substitution reaction, the alpha proton atom is substituted by an electrophile by the formation of an enol intermediate or enolate ion intermediate. Most of the carbonyl compounds go through an alpha substitution reaction.

Question

Treatment of ethyl acetoacetate with NaOEt (2 equiv) and BrCH2CH2Br forms compound X. This reaction is the rst step in the synthesis of illudin-S, an antitumor substance isolated from the jack-o’-lantern, a poisonous, saffron-colored mushroom. What is the structure of X?

several steps
NaOEt
(2 equiv)
но-
OEt
Bг
Br
он
он
illudin-S

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