Which alcohol produces more alkenes through E1 mechanism?

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In summary, alpha-terpineol and 2-methylcyclohexanol produce different alkene products through E1 mechanism, with alpha-terpineol producing four and 2-methylcyclohexanol producing two. It is uncertain which product would be formed in the greatest amount, but 2-methylcyclohexanol is a likely candidate due to potential side reactions during dehydration. Further consideration of the thermodynamic stabilities of the alkene products would be necessary to determine the exact amount.
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stanton
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[tex]\alpha[/tex]-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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  • #3
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. :)
 

What is dehydration of an alcohol?

Dehydration of an alcohol is a chemical reaction in which an alcohol molecule loses a water molecule to form an alkene.

Why is dehydration of an alcohol important?

Dehydration of an alcohol is an important reaction in organic chemistry as it is used to synthesize alkenes, which are important building blocks for various organic compounds.

What are the reagents used in dehydration of an alcohol?

The most common reagents used in dehydration of an alcohol are concentrated sulfuric acid or phosphoric acid.

What is the mechanism of dehydration of an alcohol?

The mechanism of dehydration of an alcohol involves protonation of the alcohol molecule by the acid catalyst, followed by formation of a carbocation and elimination of a water molecule to form an alkene.

What are the potential side reactions in dehydration of an alcohol?

Some potential side reactions in dehydration of an alcohol include rearrangement of the carbocation, formation of dienes, or formation of ethers if the alcohol is a secondary or tertiary alcohol.

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