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Topic: Are SN1 reactions in aprotic solvents still possible?  (Read 3376 times)

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Offline carotis

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Are SN1 reactions in aprotic solvents still possible?
« on: September 28, 2016, 11:56:16 PM »
The Prof said, it is required to conduct reactions in protic solvents, liek water to make SN1 reactions occur. My question is, do those reactions if aprotic occur just very badly, or don't SN1 reactions occurs at all? What are the possibillities if lets say a primary carbon is the leaving group for a nucleophile, E1 maybe or none?

Offline Vidya

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Re: Are SN1 reactions in aprotic solvents still possible?
« Reply #1 on: September 29, 2016, 12:18:16 AM »
leaving group on the primary carbon will give you primary carbocation which is itself is not good for SN1 or E1
Remember SN1/E1/SN2/E2 they all are always competing for reaction.Depending on the nature of the reactant,leaving group solvent and nucleophile it is decided which one is favored but it doesn't rule out all others completely.

Offline Dan

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Re: Are SN1 reactions in aprotic solvents still possible?
« Reply #2 on: September 29, 2016, 04:55:24 AM »
The Prof said, it is required to conduct reactions in protic solvents, liek water to make SN1 reactions occur. My question is, do those reactions if aprotic occur just very badly, or don't SN1 reactions occurs at all?

SN1 reactions can certainly occur in aprotic solvents, and some are routinely conducted in aprotic solvents. For example, introduction of trityl protecting groups with trityl chloride is certainly an SN1 reaction and is typically performed in dichloromethane.
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Offline kriggy

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Re: Are SN1 reactions in aprotic solvents still possible?
« Reply #3 on: September 29, 2016, 05:32:30 AM »
Usualy more important is that reagents are all dissolved. Of course, one can run reaction in suspension but I had always better results even if it resolved in some weird(ish) mixture of solvents

Offline carotis

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Re: Are SN1 reactions in aprotic solvents still possible?
« Reply #4 on: September 29, 2016, 07:15:12 PM »
I of course meant E2, was a tippo sorry :)

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