t-butoxide with secondary halide (Chad vs. Destroyer)

[whawha]

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According to Destroyer 2009, #100 and #158, a secondary halide reacts with a tert-butoxide to yield the less substituted alkene.

But, Chad is saying that it is actually the more substituted alkene that is produced from that reaction.

Which is true?

 

[vlct0ria]

According to Destroyer 2009, #100 and #158, a secondary halide reacts with a tert-butoxide to yield the less substituted alkene.

But, Chad is saying that it is actually the more substituted alkene that is produced from that reaction.

Which is true?

Pretty sure the bulky base reacts to form the less substituted product...which video of Chad's are you watching?

 

[whawha]

Pretty sure the bulky base reacts to form the less substituted product...which video of Chad's are you watching?

Ochem3 - part I

http://www.coursesaver.com/showthread.php?t=2791

 

[whawha]

The part that I was asking was in Ochem2- part II.

 

[Shinpe]

From what I remember t-butoxide is a little bit nutso and desperate, it will always give you E2 with the most available hydrogen.

I could be wrong. The better resource than either of those two would be your OC book though.

 

[whawha]

Yes, I will look it up later tonight! Thanks.