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Topic: What is the result of reacting vinylmagnesium-2-Bromo-1-propen with water (H2O)?  (Read 2795 times)

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Offline carotis

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What is the result of reacting vinylmagnesium-2-Bromo-1-propen with water (H2O)?
« on: November 23, 2015, 04:34:00 PM »
Someone could help? What is the product from this?
Is it the similiar reaction like Propen with water? I guess not because the O attacks rather the Mg than adding to the C-atom but maybe I am wrong..
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Offline Babcock_Hall

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Re: What is the result of reacting vinylmagnesium-2-Bromo-1-propen with water (H2O)?
« Reply #1 on: November 23, 2015, 06:04:20 PM »
Would you mind drawing out this compound?  I was not able to do so from your description.
« Last Edit: November 23, 2015, 07:01:42 PM by Babcock_Hall »
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Offline carotis

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Re: What is the result of reacting vinylmagnesium-2-Bromo-1-propen with water (H2O)?
« Reply #2 on: November 23, 2015, 07:54:42 PM »
sure thing :D
that's what I've come up with.
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Offline beardy

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Re: What is the result of reacting vinylmagnesium-2-Bromo-1-propen with water (H2O)?
« Reply #3 on: November 23, 2015, 11:05:49 PM »
Grignard reagents are sensitive to water. The active portion is the carbon of the carbon-metal bond. (c-mgbr). When exposed to a proton source (water can act as an acid), carbon essentially deprotonates a proton from water, breaking the c-mgbr bond and forming a new c-h bond. MgBr is now lonely (cation), so it forms an ionic bond to counter the charge with hydroxyl (anion).
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Offline beardy

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Re: What is the result of reacting vinylmagnesium-2-Bromo-1-propen with water (H2O)?
« Reply #4 on: November 23, 2015, 11:10:56 PM »
Rather odd structure, are you sure you copied it correctly?

vinylmagnesium-2-Bromo-1-propen: I think this has a valence error.
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Offline carotis

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Re: What is the result of reacting vinylmagnesium-2-Bromo-1-propen with water (H2O)?
« Reply #5 on: November 24, 2015, 07:26:13 AM »
so... the MgBr-grignard gets away as HO-Mg-Br?
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Offline Babcock_Hall

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Re: What is the result of reacting vinylmagnesium-2-Bromo-1-propen with water (H2O)?
« Reply #6 on: November 24, 2015, 08:54:10 AM »
Grignard reagents are very strong bases.  What happens when a strong base reacts with an acid?
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Offline carotis

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Re: What is the result of reacting vinylmagnesium-2-Bromo-1-propen with water (H2O)?
« Reply #7 on: November 25, 2015, 11:04:02 AM »
An H-atom leaves the carbid. Dimethylpentene would be the product. Hans't that something to do with the Zerewitinow reaction?
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Offline Babcock_Hall

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Re: What is the result of reacting vinylmagnesium-2-Bromo-1-propen with water (H2O)?
« Reply #8 on: November 25, 2015, 12:42:32 PM »
The "H" moiety leaves as a proton.  If we say "atom," it suggests that an electron is also departing (but that is perhaps being a little bit picky).  However, I agree that dimethylpropene would be the product.
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