Furfuryl chloride can undergo substitution by both SN2 and SN1 mechanisms. Since it is a 1° alkyl halide, we expect SN2 but not SN1 reactions. Draw a mechanism for the SN1 reaction shown below, with careful attention to the structure of the intermediate. How can this primary halide undergo SN1 reactions? Why is there no competition with E2 or E1 mechanisms?

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CI NaOCHo ethano H + NaCl furfuryl chloride sodium formate furfuryl formate