sn1 vs sn2 reactions in ochem 1 compared "Other than the factors we have talked about so far, solvent is another key factor that affect nucleophilic substitution reactions. Proper solvent is required to facilitate a certain mechanism. For some cases, picking up the appropriate solvent is the effective way to control which pathway the reaction proceed. To understand the solvent effect, we first of all need to have more detailed discussions about solvents, then learn how to choose good solvent for a specific reaction. Solvents can be divided into three major categories based on the structures and polarities, that is: non-polar, polar protic and polar aprotic solvents. Non-polar solvents are non-polar compounds. (hexane, benzene, toluene, etc.) Polar protic solvents are the compounds containing OH or NH group that is able to form hydrogen bonds. Polar protic solvents are highly polar because of the OH or NH group. Polar aprotic solvents is a group solvents with medium range of polarity. They are polar because of polar bonds like C=O or S=O, but the polarity is not as high as OH or NH group. Typical examples of polar aprotic solvents include acetone, DMSO, DMF, THF, CH2Cl2. The general guideline for solvents regarding nucleophilic substitution reaction is: SN1 reactions are favored by polar protic solvents (H2O, ROH etc), and usually are solvolysis reactions. SN2 reactions are favored by polar aprotic solvents (acetone, DMSO, DMF etc)."
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