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[atlanta213]

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Destroyer Road map 3

(CH3)3CO-NA+
(CH3)3COH

and C2H5O-K+
C2H5OH

on road map 3 both make carbon double bond,but location of double bond is different even thought reactant is same. Why is that?

Please explain this!

 

[JMCougar]

Ideally you'd get the Zaitsev (most substituted=most stable) alkene. This happens with the EtO-. You get the Hoffman product with tBuO- because it's just so big and sterically hindered that it can't get in close enough to pick off the H for the Zaitsev product.

 

[atlanta213]

Ideally you'd get the Zaitsev (most substituted=most stable) alkene. This happens with the EtO-. You get the Hoffman product with tBuO- because it's just so big and sterically hindered that it can't get in close enough to pick off the H for the Zaitsev product.

Thank you!

is there any other things work same as EtO- ?

 

[doc3232]

OH- and CH3O- are all small enough like ethoxide.
Mostly Tbutyl oxide and LDA are the "big" bases