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Topic: what's the nucleophile?  (Read 5578 times)

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Offline cofi

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what's the nucleophile?
« on: May 12, 2006, 07:43:43 PM »
25mL of 50:50 mixture of H2O and 2-propanol...
I add four drops of NaOH, and then four drops of tert-butyl-bromide...

what's the main nucleophile in this reaction? is it water or hydroxide ion?
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Offline Donaldson Tan

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Re: what's the nucleophile?
« Reply #1 on: May 12, 2006, 08:09:27 PM »
Here's a hint: the reaction mechanism is SN1

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Offline barcrphd

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Re: what's the nucleophile?
« Reply #2 on: May 12, 2006, 11:20:18 PM »
you must be knowing NaOH is a strong base. what is the doubt... OH is the nucliophili here.
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Offline cofi

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Re: what's the nucleophile?
« Reply #3 on: May 13, 2006, 03:15:50 AM »
Quote from: geodome on May 12, 2006, 08:09:27 PM
Here's a hint: the reaction mechanism is SN1

yeah, I know that...
but... I still don't understand... why should that matter...
explain, please...

TIA,
 F
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Offline cofi

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Re: what's the nucleophile?
« Reply #4 on: May 13, 2006, 03:53:29 AM »
here's what I found out...
OH- is a strong nucleophile, but it is strongly solvated in water too, so that doesn't really matter :)
I have H2O as a part of the solvent, so it will be the main nucleophile in this reaction :)

is this correct?
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Offline plu

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Re: what's the nucleophile?
« Reply #5 on: May 14, 2006, 04:03:17 PM »
You have a 50:50 mixture of water and 2-propanol.  Both can act as the nucleophile in your reaction, giving a mixture of products.
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Offline Donaldson Tan

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Re: what's the nucleophile?
« Reply #6 on: May 16, 2006, 08:42:35 AM »
Quote from: geodome on May 12, 2006, 08:09:27 PM
Here's a hint: the reaction mechanism is SN1

Nucleophile strength is not a deciding factor. Population is.

Which nucleophile is in present greatest proportion?
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"Say you're in a [chemical] plant and there's a snake on the floor. What are you going to do? Call a consultant? Get a meeting together to talk about which color is the snake? Employees should do one thing: walk over there and you step on the friggin� snake." - Jean-Pierre Garnier, CEO of Glaxosmithkline, June 2006
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