Tricky Organic Chemistry Question


Comments

  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?

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

    ReplyDelete
  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?

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

    ReplyDelete
  5. Neighbouring group participation?

    ReplyDelete

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