This problem is from a chapter with ONLY SN2 reactions. The configuration of the

Question

This problem is from a chapter with ONLY SN2 reactions. The configuration of the new substituent at the end versus the old is somehow the SAME afterwards even though it normally inverts. The only way I can think of this happening is through a double inversion WITHOUT doing an SN1 reaction. Is this mechanism possible with DMF acting as the first nucleophile? DMF normally does't do this from what I know. Also, whouldn't it experience steric hindrance? Can someone please explain if this is possible and why? If it is not possible, what is the real mechanism?

Explanation / Answer

In this mechanism DMF is a polar solvent and it acts as first nucleophile. if you take pyridine in reaction then pyridine also acts as a nucleophile and those type of reactions re called SNi reactions, substittution nucleophilic interolecular reactions. then nucleophile CH3SH attacks the substrate and forms retention product

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