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Topic: Lucas Test  (Read 7831 times)

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Offline KingV15

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Lucas Test
« on: February 26, 2012, 12:53:40 AM »
Explain the following reactivity order during a Lucas test:
3-methyl-1-buten-3-ol > 2-methyl-1-buten-3-ol > 3-methylbutan-2-ol > 3-methylbutan-1-ol

-I know that 3° alcohols react very fast with the Lucas reagent, secondary reacts slowly, and primary tend not to react at all at room temperature.
I am not sure how to account for the order above because I'm getting:
3-methyl-1-buten-3-ol-primary alcohol
2-methyl-1-buten-3-ol -
3-methylbutan-2-ol –Secondary alcohol
3-methylbutan-1-ol-primary alcohol
Any thoughts?

Offline vivekrai

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Re: Lucas Test
« Reply #1 on: February 26, 2012, 06:42:38 AM »
What type of mechanism does Lucas test follows : SN1 or SN2 ?? Think (check Wikipedia). And then determine what type of the reagents you have at hand.
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Offline Arctic-Nation

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Re: Lucas Test
« Reply #2 on: February 26, 2012, 07:20:18 AM »
3-methyl-1-buten-3-ol-primary alcohol

Any thoughts?
Methinks you should think some more about this one. Or draw it out on a piece of paper.

Offline rajajidwivedi

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Re: Lucas Test
« Reply #3 on: April 14, 2012, 10:48:01 AM »
this is all due to stability of carbocation formed in the reaction.

Offline me-go

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Re: Lucas Test
« Reply #4 on: April 17, 2012, 12:19:36 PM »
3-methyl-1-buten-3-ol ==>  tertiary allylic alcohol ==> stable cabocation so it has fastest reaction in lucas test,

reactivity order during a Lucas test depends on carbocations:

tropylium> 3 benzylic > 3 allylic > 2 benzylic > 2 allylic > 1 benzylic > 3 > allylic > 2 > 1 > Me+ > vinylic > phenyl

 ;)

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