Question : destroyer roadmap #3 (picture)

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I Brush My Teeth

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Can someone tell me why these two reactions yield different products?

I thought it was just a simple E2 where a double bond would be made at the most stable carbon
 

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Can someone tell me why these two reactions yield different products?

I thought it was just a simple E2 where a double bond would be made at the most stable carbon


The are indeed BOTH E2 reactions. Look closely at the employed base. If C2H5O-/C2H5OH is used we do a Zaitsev elimination whereby the most substituted alkene is formed. In the reaction going at the top, a larger, sterically hindered base was used, We used Sodium t-Butoxide...this reagent gave E2 Hoffmann, whereby the less substituted alkene was formed. For further clarity, see the David Klein text book which gives many more examples of this VITAL reaction series.

Hope this helps

Dr. Jim Romano
 
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