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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?
Yes, there is a cylic intermediate. There is S atom and is involved in the reaction as well as a nucleophile.
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?
Hi WeiJie, you are almost there. Can anyone refine the solution that WeiJie has?