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- Aug 16, 2011
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Hi I am having trouble finding a textbook that will tell me about the possible stereochemical of using these reagents during alcohol reactions.
Of all the reagents I looked at: TsCl and MsCl and Hbr (Hbr provides protons so that OH can turn into H20 and leave) they all turn the OH into a good LG so that a halide or Nu can come in and attack. These guys follow the same rules of Sn1 and Sn2, inversion and racemization are possible depending on the stereochemistry provided.
The only exception I found is SoCl2, this reagent is used specifically to retain stereochemistry so there is no inversion. Is this correct?
Of all the reagents I looked at: TsCl and MsCl and Hbr (Hbr provides protons so that OH can turn into H20 and leave) they all turn the OH into a good LG so that a halide or Nu can come in and attack. These guys follow the same rules of Sn1 and Sn2, inversion and racemization are possible depending on the stereochemistry provided.
The only exception I found is SoCl2, this reagent is used specifically to retain stereochemistry so there is no inversion. Is this correct?