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Topic: Aldehyde Reaction Question  (Read 3690 times)

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Offline shell52080

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Aldehyde Reaction Question
« on: March 14, 2007, 11:39:36 AM »
I'm having a really hard time figuring out this reaction:

cyclohexanone + CH3-Br ---->(react with Ph3P) ------>(reacts with n-BuLi)

My guess would be that Ph3P forms a bond with the CH3-Br. The n-BuLi would then pull off an H resulting in CH2PhP3. Would the final answer be cyclohexane with a double bond CH2 attached to it?

Thanks

Offline Dolphinsiu

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Re: Aldehyde Reaction Question
« Reply #1 on: March 14, 2007, 11:56:30 AM »
Wittig reaction

Ph3P + RCH2X --THF--> Ph3P+ -- RCH2X- --n-BuLi--> Ph3P+ -- C- HR (ylide)


Offline AWK

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Re: Aldehyde Reaction Question
« Reply #2 on: March 14, 2007, 01:54:58 PM »
See reaction mechanism - you lost an oxygen
AWK

Offline shell52080

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Re: Aldehyde Reaction Question
« Reply #3 on: March 14, 2007, 03:07:58 PM »
I thought the oxygen bonded with the Ph3P. I still don't get it.

Offline alphahydroxy

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Re: Aldehyde Reaction Question
« Reply #4 on: March 15, 2007, 04:05:31 AM »
I thought the oxygen bonded with the Ph3P. I still don't get it.


It does! Just google the "wittig reaction" and everything shall become clear...


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