E1 and heat

[chiddler]

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Example given in book is 2-methylcyclopentanol. (for ease of visualization: cyclopentane, top carbon alcohol, adjacent carbon has methyl)

Which is the product?

Answer is C.

I do not need help with this question; I understand it perfectly. Rather, a modified version of this question.

What if we gradually lower the temperature of this reaction. Which other products could E1 produce? (ignore E2's, and SN1/2's)

What I think: In addition to the product above, the carbocation shifts to the tertiary carbon. Then elimination can occur with product A as well. But, C is still major product.

Right?

 

[MedPR]

Right. Even at a high temp A should be a minor product.

 

[chiddler]

cool.

MOAR

?

(in addition to the product where E is at 2, Nu is at 3)

 

[MedPR]

Yes. That would be the major product since it hydride shifts to form a tertiary carbocation.