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Topic: grignard addition  (Read 4267 times)

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Offline orgoclear

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grignard addition
« on: December 23, 2009, 11:18:18 AM »
(CH3)2CHCOCH(CH3)2+(CH3)2CMgBr (G.R) --> ________

The substrate is too much sterically hindered and too much deactivated for nucleophilic addition at the carbonyl carbon (4 ERG's) .. So in this condition what will happen ? Will a reaction occur?

Offline kimyacı

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Re: grignard addition
« Reply #1 on: December 23, 2009, 02:23:32 PM »
 maybe grignard compound can remove of one H that adjacent to carbonyl group.because you know these hydrogens are acidic.

Offline azmanam

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Re: grignard addition
« Reply #2 on: December 23, 2009, 03:18:10 PM »
I've also seen Grignards act as a reductant much like a MVP reduction.  Watch for that.
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Offline orgopete

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Re: grignard addition
« Reply #3 on: December 23, 2009, 04:42:04 PM »
I too was going to note the reduction to give the alkoxide and propene (in this case). If that reaction occurs, or if you form enolate directly, or if the addition is slow, the product is another alkoxide, then you can have products derived from the alkoxide, such as aldol products as well.
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Offline Quaff

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Re: grignard addition
« Reply #4 on: January 05, 2010, 05:22:43 PM »
(CH3)2CHCOCH(CH3)2+(CH3)2CMgBr (G.R) --> ________

The substrate is too much sterically hindered and too much deactivated for nucleophilic addition at the carbonyl carbon (4 ERG's) .. So in this condition what will happen ? Will a reaction occur?

Structure of GR is not correct.

Offline bolo

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Re: grignard addition
« Reply #5 on: January 09, 2010, 01:00:31 PM »
There will a reducion occur (2,4-dimethyl-3-pentanol + propene).

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