View Full Version : Orgo Question!


tisler
07-04-2008, 08:14 AM
I've been studying destoyer and it tells me that t-butoxide(if i spelled it right) favors unstable double bond in E2. However, ethoxide follows zaitsev rule. Can anybody tell me why?

Orgodox
07-04-2008, 09:12 AM
First of all its not unstable the double bond its just less substituted which makes it less favorable.

The answer is because t-butoxide is big and bulky and cant dig into the middle to pull off a H, but EtO- is much smaller and can get in there to take off the H to form more stable zaitsev product

PooyaH
07-04-2008, 10:51 AM
First of all its not unstable the double bond its just less substituted which makes it less favorable.

The answer is because t-butoxide is big and bulky and cant dig into the middle to pull off a H, but EtO- is much smaller and can get in there to take off the H to form more stable zaitsev product

:thumbup:

tisler
07-04-2008, 12:12 PM
First of all its not unstable the double bond its just less substituted which makes it less favorable.

The answer is because t-butoxide is big and bulky and cant dig into the middle to pull off a H, but EtO- is much smaller and can get in there to take off the H to form more stable zaitsev product

oh...i see how it works.
Thank you so much:)