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Topic: RLi and alcohols  (Read 2813 times)

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Offline dscot

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RLi and alcohols
« on: January 08, 2013, 04:15:55 PM »
Hey,

I was just wondering how an alcohol such as methanol would effect an organolithium? I know with regards to air they instantly react but not sure about the situation with alcohol?

Thank you!
Dave
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Offline sjb

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Re: RLi and alcohols
« Reply #1 on: January 08, 2013, 04:18:40 PM »
Quote from: dscot on January 08, 2013, 04:15:55 PM
Hey,

I was just wondering how an alcohol such as methanol would effect an organolithium? I know with regards to air they instantly react but not sure about the situation with alcohol?

Thank you!
Dave

How do they react with air? What kind of reagent is an organolithium?
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Offline dscot

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Re: RLi and alcohols
« Reply #2 on: January 08, 2013, 04:22:46 PM »
Hi Sjb,

They react vigorously with air and must be used in a protective environment.

They have bonds between C-Li , an example would be nBuLi.

Thanks!
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Offline DrCMS

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Re: RLi and alcohols
« Reply #3 on: January 08, 2013, 05:05:01 PM »
What sjb was asking you was what is it in the air that reacts with the organolithium reagent?
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Offline dscot

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Re: RLi and alcohols
« Reply #4 on: January 08, 2013, 05:12:31 PM »
Hi DrCMS,

Ah ok I think I understand now, they react with the oxygen in the air and so will react with the oxygen from the alcohol. Which means they also react vigorously in alcohol as well as air?


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Offline Babcock_Hall

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Re: RLi and alcohols
« Reply #5 on: January 08, 2013, 06:42:36 PM »
I don't agree that the two reactions will necessarily be the same.
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Offline fledarmus

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Re: RLi and alcohols
« Reply #6 on: January 08, 2013, 09:00:13 PM »
What do you know about the acidity or basicity of organolithium reagents and alcohols?
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Offline dscot

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Re: RLi and alcohols
« Reply #7 on: January 09, 2013, 04:55:18 AM »
I think that RLi are strong bases?
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Offline Babcock_Hall

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Re: RLi and alcohols
« Reply #8 on: January 09, 2013, 09:29:59 AM »
Yes, they are strong bases.  Are there any acid protons around?
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