Furfuryl chloride can undergo substitution by both SNN2 and SNN1 mechanisms. Because it is a 1∘∘ alkyl halide, we expect SNN2 but not SNN1 reactions. Draw a mechanism for the SNN1 reaction shown below, paying careful attention to the structure of the intermediate

Organic Chemistry: A Guided Inquiry
2nd Edition
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Author:Andrei Straumanis
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Chapter14: Elimination
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Problem 24CTQ
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Furfuryl chloride can undergo substitution by both SNN2 and SNN1 mechanisms. Because it is a 1∘∘ alkyl halide, we expect SNN2 but not SNN1 reactions. Draw a mechanism for the SNN1 reaction shown below, paying careful attention to the structure of the intermediate.

Furfuryl chloride can undergo substitution by both SN2 and SN1 mechanisms. Because it is a 1° alkyl halide, we expect SN2 but not SN1 reactions. Draw a mechanism for the SN1 reaction
shown below, paying careful attention to the structure of the intermediate.
ethanol
+
NaOCHO
H.
+
NaCl
furfuryl chloride
sodium formate
furfuryl formate
Edit the reaction by drawing all steps in the appropriate boxes and connecting them with reaction arrows. Add charges where needed. Electron flow arrows should start on an
atom or a bond and should end on an atom, bond, or location where a new bond should be created.
L.
H
N
Br
+
(1]
H.
- O.
Transcribed Image Text:Furfuryl chloride can undergo substitution by both SN2 and SN1 mechanisms. Because it is a 1° alkyl halide, we expect SN2 but not SN1 reactions. Draw a mechanism for the SN1 reaction shown below, paying careful attention to the structure of the intermediate. ethanol + NaOCHO H. + NaCl furfuryl chloride sodium formate furfuryl formate Edit the reaction by drawing all steps in the appropriate boxes and connecting them with reaction arrows. Add charges where needed. Electron flow arrows should start on an atom or a bond and should end on an atom, bond, or location where a new bond should be created. L. H N Br + (1] H. - O.
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