Bootcamp Error (or I'm stupid)

[ichoai]

Hey guys, I was wondering if any of you noticed that there's a bootcamp error on the Orgo exam # 4 (Question 5)

It says that this compound undergoes E2 reaction and that it is best described by "The lease stable antiperiplanar conformation that leads to the formation of the minor product"

While this is the least STABLE conformation due to the tertbutyl groups both on the wedge, there is only 1 Beta Hydrogen, leading this "least stable" conformation to the MAJOR product.

If I am wrong, someone please tell me. haha

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[Daneosaurus]

There are two ß Hydrogens on Carbon 3. But, only one of them is antiperiplanar to Bromine. Not sure what the error is, or what your question is.

 

[ichoai]

There is only one product, so how can it be considered major or minor? In this case, the only Beta Hydrogens are on Carbon 3... Usually when questions are looking for the major product there are multiple Beta hydrogens allowing for the least substituted alkene, in this case the only possible product is the most substituted..so how does the least stable antiperiplanar conformation lead to the MINOR product?

 

[Daneosaurus]

There is only one product, so how can it be considered major or minor? In this case, the only Beta Hydrogens are on Carbon 3... Usually when questions are looking for the major product there are multiple Beta hydrogens allowing for the least substituted alkene, in this case the only possible product is the most substituted..so how does the least stable antiperiplanar conformation lead to the MINOR product?

I was wondering the same thing. From what I can tell, there is only one possible product from E2 elimination.

 

[ichoai]

As far as the DAT is concerned, I doubt this will ever be an issue, but I was just curious if I was missing something..

 

[Ari Rezaei]

Well you could rotate the carbon since it's a single sigma bond, right? In that case the tert butyl groups would be on opposite sides, and with E2 elimination you'd get the most stable conformation leading to the major product.

The question is asking about that specific conformation though, as such it's the least stable conformation leading to the minor product.

 

[ichoai]

ahhhhh. That's what I was missing.

Thanks.

 

[Daneosaurus]

Well you could rotate the carbon since it's a single sigma bond, right? In that case the tert butyl groups would be on opposite sides, and with E2 elimination you'd get the most stable conformation leading to the major product.

The question is asking about that specific conformation though, as such it's the least stable conformation leading to the minor product.

Oh! Ok. That helps me too.