Tricky Organic Chemistry Question


  1. Why would there be a cyclic intermediate?
    The only possible mechanism I could come up with is the SN2 mechanism, with the CH3CH2O- nucleophile from the dissociation of ethanol.
    Is this right?

  2. Yes, there is a cylic intermediate. There is S atom and is involved in the reaction as well as a nucleophile.

  3. The S atom attacks the carbon next to chloride to displace it and form a three member cyclic ring. Since 3 member ring is quite strain, it is reactive.

    The nucleophile CH3CH2O- attacks the three member ring to form the product. Is that correct?

  4. Hi WeiJie, you are almost there. Can anyone refine the solution that WeiJie has?

  5. Neighbouring group participation?


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