Contradiction in orgo

[hasanein4u]

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Chad says that we eliminate from the least substituted Beta carbon only if we have both tertiary base and tertiary alkyl halide
and he gave another example when we have tertiary base with secondary alkyl halide and it was normal elimination from the most substituted carbon

BUT in destroyer in question 134
the second step
it has tertiary base and they eliminated from the least substituted carbon though their alkyl halide is not tertiary!!

so which one is correct... Chad who says that both base and alkyl halide have to be tertiary in order to eliminate from the least substituted carbon... or destroyer who says the tertiary base is enough to do it even if the alkyl halide is not tertiary?

 

[aqz]

You only need EITHER the base or the LG to be bulky/tertiary, not both. And if you do have both, it would still deprotonate the least substituted carbon (Hofmann product).

Someone correct me if I'm wrong.

 

[hasanein4u]

You only need EITHER the base or the LG to be bulky/tertiary, not both. And if you do have both, it would still deprotonate the least substituted carbon (Hofmann product).

Someone correct me if I'm wrong.

That means Destroyer is correct and chad is wrong

 

[Dotoday]

Yes, big tertiary base will lead to a Hoffman product. Whenever you see T- butoxide, Hoffman is your best bet. Destroyer is correct here. Hope this helps.

Sent from my MB855 using Tapatalk

 

[NDPitch]

go over to course saver, and look at this thread.

/showthread.php?4582-Question-about-bulky-bases