Which alcohol produces more alkenes through E1 mechanism?

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The discussion centers on the dehydration of α-terpineol and 2-methylcyclohexanol via the E1 mechanism, leading to the formation of alkenes. α-Terpineol produces four different alkene products, including imonene, while 2-methylcyclohexanol yields two alkenes. A key point of debate is which compound will produce its respective alkenes in greater amounts. One viewpoint suggests that 2-methylcyclohexanol will yield more due to potential side reactions involving α-terpineol, such as the formation of ethers and polymeric alkenes from carbocation intermediates. However, another perspective emphasizes the importance of considering the thermodynamic stability of the alkene products to determine which will be formed in the largest quantity, rather than focusing solely on potential side reactions. The conversation highlights the complexity of reaction pathways and product distribution in dehydration reactions.
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\alpha-terpineol produces four different alkene products (including imonene) when it is dehydrated via E1 mechanism.
On the other hand, 2-methylcyclohexanol produces two different alkenes through E1 mechanism.

Which of these product do you think would be formed in the greatest amount? I personally think 2-methylcyclohexanol will be formed in larger amount. Here's my explanation:2-methylcyclohexanol has more product since alpha-terpineol might have more side reactions during dehydrations. (carbocation+alcohol --> ether / carbocation+alkene --> plymeric alkene)

I am not completely sure. What do you think? Alpha-terpineol or 2-methylcyclohexanol?
 

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Am I misunderstanding the question or are you: it sounds like it's asking, "Which of the alkene products of the dehydration of 2-methylcyclohexanol would be formed in the largest proportion?"

Carbocation + alcohol -(acid)-> ether? possible..

carbocation + alkene -(acid)-> polymeric alkene? maybe...

I don't think either of those two proposed reactions are relevant here. If I were you, I'd consider the thermodynamic stabilities of all the alkene products to determine which one is formed in greatest quantity.
 
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Carbocation + alcohol -(acid)-> ether?

carbocation + alkene -(acid)-> polymeric alkene?
They wre just an example of the side reactions that could occur. Those reactions might disturb the yield. Thank you for your advice. :)
 

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