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Topic: Acetonitrile as a nucleophile in Sn2 reactions.  (Read 26367 times)

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Offline Twickel

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Re: Acetonitrile as a nucleophile in Sn2 reactions.
« Reply #15 on: April 08, 2012, 05:43:32 AM »
Thank you. So the TsO is actually bonded to the chain like so?
The benzene ring is attached to the carbon, the S is bonded to the ring, and the 3 oxygens are bonded to the sulfur. How does it leave?

If I draw a curly arrow going to the ring it has a carbon bonded to 5 things. Sorry if I am not making any sense

Offline Twickel

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Re: Acetonitrile as a nucleophile in Sn2 reactions.
« Reply #16 on: April 08, 2012, 05:52:48 AM »
I drew a structure, is that what TsO looks like?

Ignore the H bonded to the O, pretends its just an O

Offline discodermolide

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Re: Acetonitrile as a nucleophile in Sn2 reactions.
« Reply #17 on: April 08, 2012, 05:53:13 AM »
Thank you. So the TsO is actually bonded to the chain like so?
The benzene ring is attached to the carbon, the S is bonded to the ring, and the 3 oxygens are bonded to the sulfur. How does it leave?

If I draw a curly arrow going to the ring it has a carbon bonded to 5 things. Sorry if I am not making any sense

Here is another picture
This is what tosyl looks like

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Offline Twickel

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Re: Acetonitrile as a nucleophile in Sn2 reactions.
« Reply #18 on: April 08, 2012, 05:56:30 AM »
Ok, so now  get it, weird I clicked Tos in my chem sketch and it added it like so. Simply forms an anion.
There is no TsO option.

Offline Twickel

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Re: Acetonitrile as a nucleophile in Sn2 reactions.
« Reply #19 on: April 08, 2012, 06:02:09 AM »
One more questions.
This is a radical reaction.
So I did the reaction and mechanisms and in the end, I simply replaced the Br with a hydrogen.
How do they get the rings as the products?
I was thinking anti markovnikov addition, but it doesnt add to the double bond, the radical reaction is on the other side.

Offline discodermolide

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Re: Acetonitrile as a nucleophile in Sn2 reactions.
« Reply #20 on: April 08, 2012, 06:08:29 AM »
One more questions.
This is a radical reaction.
So I did the reaction and mechanisms and in the end, I simply replaced the Br with a hydrogen.
How do they get the rings as the products?
I was thinking anti markovnikov addition, but it doesnt add to the double bond, the radical reaction is on the other side.



Sorry I don't follow, what is a radical reaction?
Your document shows the same two reactions
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Offline Twickel

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Re: Acetonitrile as a nucleophile in Sn2 reactions.
« Reply #21 on: April 08, 2012, 06:10:22 AM »
Hi
Sorry fixed it up. Now attached.
I am talking about a radical chain reaction. With initiation and propagation.

Offline discodermolide

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Re: Acetonitrile as a nucleophile in Sn2 reactions.
« Reply #22 on: April 08, 2012, 06:13:11 AM »
Hi
Sorry fixed it up. Now attached.
I am talking about a radical chain reaction. With initiation and propagation.


It may be better to start a new thread so it is differentiated from the previous one.
I'm sure one of the admins can arrange this
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Offline Twickel

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Re: Acetonitrile as a nucleophile in Sn2 reactions.
« Reply #23 on: April 08, 2012, 06:15:43 AM »
Will now make a new thread. Thanks for helping me out.

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