Furfuryl ethyl ether (FEE) was identiied as a component that forms in aged beer, giving ita solvent-like taste U. Agric. Food Chem, 2004, 52, 1661) This ether can be formed fom furfuryl alcnhol (FAL, by either S.1 or S2 mechanisms. CH,CHOH OCH,CH, furtury alcohol (prolonated) furfury ethyl ether FEE) Draw a reasonable mechanism of the SN1 formation of FEE. Explain why it is possible for FALC to undergo a SN1 reaction, even though it would have to form a primary carbocation.

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Furfuryl ethyl ether (FEE) was identified as a component that forms in aged beer, giving it a
solvent-like taste U. Agric. Food Chem, 2004, 52, 1661) This ether can be formed from
furfuryl alcohol (FALC, by either S,1 or S2 mechanisms.
CH,CH,OH
OCH,CH,
furtury alcohol
(prolonatec)
furfuryl ethyl ether
FEE)
Draw a reasonable mechanism of the SN1 formation of FEE.
Explain why it is possible for FALC to underga a SNI reaction, even
though it would have to form a primary carbocation
Transcribed Image Text:Furfuryl ethyl ether (FEE) was identified as a component that forms in aged beer, giving it a solvent-like taste U. Agric. Food Chem, 2004, 52, 1661) This ether can be formed from furfuryl alcohol (FALC, by either S,1 or S2 mechanisms. CH,CH,OH OCH,CH, furtury alcohol (prolonatec) furfuryl ethyl ether FEE) Draw a reasonable mechanism of the SN1 formation of FEE. Explain why it is possible for FALC to underga a SNI reaction, even though it would have to form a primary carbocation
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