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Offline darewinder

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nucleophile substitution question
« on: October 29, 2008, 07:29:59 PM »
Hi, I had a question about nucleophile substitution. For an sn1 reaction. Is the solvent the same thing as nucleophile? Sometimes they ask you questions about the major produced compound but they dont give you solvent, so what do we assume as solvent.

Also I had this question in book. CH3CH2CH2-Cl  +  P(CH3)3

They asked us the major predicted producted.

Im guessing the reaction has to be sn2 since the carbon is primary. so it should produce the inversion reaction.

But the book had the answer like this, CH3CH2CH2-P+(CH3)3  +  Cl-

and i guessed that it isnt inversion because the carbon the P and the Cl that was connected to wasn't a chiral carbon.

Is this right?

Thanks

Offline macman104

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Re: nucleophile substitution question
« Reply #1 on: October 29, 2008, 08:15:58 PM »
Hi, I had a question about nucleophile substitution. For an sn1 reaction. Is the solvent the same thing as nucleophile? Sometimes they ask you questions about the major produced compound but they dont give you solvent, so what do we assume as solvent.
You assume the solvent isn't important.  The solvent is not the same as the nucleophile, sometimes, the solvent may act as a nucleophile, but don't assume that.
Quote
Also I had this question in book. CH3CH2CH2-Cl  +  P(CH3)3

They asked us the major predicted producted.

Im guessing the reaction has to be sn2 since the carbon is primary. so it should produce the inversion reaction.

But the book had the answer like this, CH3CH2CH2-P+(CH3)3  +  Cl-

and i guessed that it isnt inversion because the carbon the P and the Cl that was connected to wasn't a chiral carbon.

Is this right?

Thanks
Yea, it technically should produce inversion, but you don't have a chiral compound, so it doesn't really have any noticeable effect.

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