Organic Chemistry : Substitution Mechanisms
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Example Question #11 : Substitution Mechanisms
Which of the following molecules would most readily undergo an SN2 mechanism?
I
III
II
V
IV
IV
Example Question #1 : Help With Sn2 Reactions
Suppose that a chemistry student is trying to run a reaction in the lab. In his solution, he adds 
What is the most likely reason for why the addition of hydrochloric acid to the solution allowed the reaction to proceed?
The addition of hydrochloric acid to the solution protonates the hydroxyl group on ethanol, allowing it be a better leaving group.
The addition of hydrochloric acid increased the energy of the transition state of the reaction, which resulted in enough energy to drive the reaction forward.
The addition of hydrochloric acid protonated the solvent and, as a result, the reaction was able to move forward because DMF is a polar aprotic solvent.
The addition of hydrochloric acid resulted in an increase in the concentration of chloride ion, which increased the reaction rate and drove the reaction forward.
The addition of hydrochloric acid to the solution protonates the hydroxyl group on ethanol, allowing it be a better leaving group.
In this question, we're presented with a scenario in which a chemistry student is trying to run a reaction. At first, the reaction doesn't work. But after the student adds a strong acid to the mixture, the reaction goes through. We're being asked to determine why this happens.
First and foremost, let's identify which kind of reaction is occurring. The student starts with 
Before addition of 
But, this all changes once 
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