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Chemistry, 20.07.2019 00:30 stranger123

In a 2004 article, vanderhaegen et al. (journal of agricultural and food chemistry 2004,52(6), 1661- 1668) describe the formation of furfuryl ethyl ether (fee) in beer from two possible precursors, 2- furyl alcohol (falc) and 2-furfuryl acetate (fac), reacting with ethanol in an acid-catalyzed mecha- nism. they propose several interconnected routes leading to the ether functional group of fee. read the article (link to pdf) and answer questions below. 1. draw the three-step mechanism of formation of fee from fac. 2. the authors believe that the displacement by ethanol to produce furfuryl ethyl ether involves an sn 2 type mechanism, as opposed to an sn1 mechanism. what reasons do they provide to support the hypothesized sn2 mechanism? 3. beer is a complex mixture that contains a number of different substances. the concentrations of other nucleophiles in beer are low relative to that of ethanol. however, small amounts of products may form that affect the taste of beer due to their low flavor thresholds, meaning these substances can affect flavor at very low concentrations. these potential side reactions are represented in figure 3 using a generalized nucleophile (nuc). the authors cite one specific compound that might be produced in beer that has a roasted, coffee-like aroma. draw the structure of this compound.

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