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Topic: Dehydration of 2-methylcyclohexanol  (Read 11213 times)

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Offline Sis290025

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Dehydration of 2-methylcyclohexanol
« on: October 31, 2006, 09:02:08 AM »
According to the microscale dehydration of 2-methylcyclohexanol experiment, two isomers can be formed:  1-methycyclohexene and 3-methylcyclohexene. Which isomer do you expect to be the predominant product? 

Would the predominant isomer be 1-methylcyclohexene? From Saytzeff's rule, it states that in the formation of an alkene hydrogen is lost from the C atom, which has fewer H atoms, that is next to C atom bonded to the leaving group. The C atom bonded to the CH3 group only has 1 H.   

Thanks.

Offline Yggdrasil

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Re: Dehydration of 2-methylcyclohexanol
« Reply #1 on: October 31, 2006, 01:03:20 PM »
Yes, 1-methylcyclohexene will be the predominant product.  Another way to look at it is that 1-methylcyclohexene is the more stable product since more highly substituted alkenes are more stable (due to hyperconjugation).

Offline Sis290025

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Re: Dehydration of 2-methylcyclohexanol
« Reply #2 on: November 01, 2006, 09:11:35 AM »
I have another question about the general dehydration experiment.

Why is the alkene that was distilled from the dehydration reaction washed with a base solution?

Is this to neutralize the remaining traces of acid?

Thanks again.

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