Br КОЕBИ

Living By Chemistry: First Edition Textbook
1st Edition
ISBN:9781559539418
Author:Angelica Stacy
Publisher:Angelica Stacy
ChapterU1: Alchemy: Matter, Atomic Structure, And Bonding
SectionU1.1: Tools Of The Trade: Lab Equipment And Safety
Problem 8E
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What is the following E2 mechanism? I tried using the wedge hydrogen on the chiral center with the dash methyl to kick out the leaving group and make an alkene but was told it was wrong. 

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КОЕBИ
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t-butoxide can be used to form the “less substituted” alkenes in elimination reactions (the E2, specifically). Usually, the elimination reactions favour the “more substituted” alkene (the Zaitsev product)  . But  when t-butoxide is used, it will preferentially remove the proton from the smaller group. This produces the so-called “Hoffmann” product.

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