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9.6 Using All Four Factors
The solvent shell is preventing the nucleophile from doing what it is supposed to do.
The solvent shell is the first thing the nucleophile needs to do.
solvent shells around negative charges are not formed very well by polar aprotic solvents.
The nucleophile does not have a solvent shell, so it is said to be naked.
Before it can react with something, it doesn't need to shed a solvent shell.
It didn't have a solvent shell to begin with.
The effect is very drastic.
A nucleophilic with a solvent shell will spend most of its existence with the shell, and there will be only brief moments when it is free to react.
We are speeding up the reaction by allowing the nucleophile to react all the time.
S 2 reac N tions can occur thousands of times faster than regular protic solvent reac N tions.
If a solvent is indicated, you should look to see if it is one of the polar aprotic solvents listed above.
It is a good bet that the reaction will be S 2.
Even though the substrate is secondary, a N reaction is still possible.
If you want to copy the list on a blank piece of paper, go back to the list and study it.
We need to see how to put all four factors together.
When analyzing a reaction, we need to look at all four factors and make a determination of which mechanism is predominating.
There is a strong nucleophile in a polar solvent.
Determine if the reaction will proceed via an S 2 or an S 1 mechanism by looking at all of the reagents and conditions.
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