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Can you predict an undesirable side reaction that might occur using ethanol as a solvent that...

Can you predict an undesirable side reaction that might occur using ethanol as a solvent that

would not occur if we used THF as a solvent in an Sn2 reaction

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Answer #1

THF is a polar aprotic solvent which stabilize the transition state of SN2 reaction .Hence, it is used in SN2 reaction.

Changing the solvent from THF to ethanol will greatly affect the product and mechanism.

Ethanol is a polar protic solvent which stabilize the transition state of SN1 reaction . Hence , it is used in SN1 reaction.

It means changing the solvent from THF to ethanol will get us SN1 reaction instead of SN2 reaction . In SN2 we get high percentage of one chiral product but in SN1 we get equal amount of enantiomers and the product become racemic (not chiral.)

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