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Michael Georgiades

Nucleophilic Substitution and Solvent Effects

David Plantz  Follow
I think you are on the right track (except the word solvent vs reactant). I think you should think about the t-butyl product. There are two reasons the ratio is not 1:1. You gave a predicted result, what could be another? (Hint, could a product also be a reactant?)

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Bob Singer  Follow
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Did you observe a solvent effect in this experiment?
You can't have observed a solvent effect in this experiment, because you were reacting different substrates in the same solvent. To observe a solvent effect, you need to react the same substrate in different solvents, and see whether you can relate any differences in the results to the different character of the solvents.
I'm not saying there isn't a solvent effect, or that the points you make are wrong, but you can't observe it unless you compare the same reaction in different solvents.
In this experiment, the differences are primarily due to the different mechanisms of SN2 and SN1 in the same solvent.

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Carolyn Barnett  Follow
MJC hit the nail on the head.

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