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Topic: Sn1 and SN2 questions  (Read 4876 times)

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Offline kli1

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Sn1 and SN2 questions
« on: May 12, 2008, 11:06:04 AM »
See for a Sn1 reaction is the nucleophile always water?

Also I have a question that asks for the difference in the stereochemical outcomes of the two reactions. I know that sn2 undergoes inversion but not sure what to put for the SN1 reaction.

Can someone help please?

Offline tamim83

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Re: Sn1 and SN2 questions
« Reply #1 on: May 12, 2008, 11:16:12 AM »
For an Sn1 reaction, the solvent can be the nucleophile.  The solvent can be water, but you can also have alcohols acting as nucleophiles. 

Sn1 reactions can produce racemic products because the carbocation intermediate is sp2 hybridized.  The nucleophile can then add above or below the plain of the cation, producing a nearly 50:50 mixture of R and S enantiomers. 

Offline se7en47

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Re: Sn1 and SN2 questions
« Reply #2 on: May 19, 2009, 02:00:03 AM »
I understand that a protic solvent is able to stabilize a transition state by forming hydrogen bonds with the leaving group, but my question is how or when do you know a protic solvent can increase or decrease the rate of a reaction?

I think this also has something to do with solvent polarity but I'm a bit unsure about this as well

thanks

EDIT: actually I think I might have come across something, so basically if you have a more polarized solvent then the rate of reaction will increase? and vice versa? Also I think I know why but, again, I am not too sure. If anyone could let me know that would be Awesome!!!
« Last Edit: May 19, 2009, 02:13:30 AM by se7en47 »

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