a. Draw fructose and identify the three alcohol functional groups involved in the dehydra- tion reactions necessary to convert fructose into hydroxymethylfurfural. HO b. Draw the mechanism for each (one of them includes an enol tautomeriza- tion reaction!).

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Chapter1: Chemical Foundations
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3. The Seliwanoff Test tests for ketoses by forming hydroxymethylfurfural
(shown below) when heated with a strong mineral acid. This compound forms
a red complex with resorcinol (1,3-dihydroxybenzene). The Seliwanoff reagent
is a freshly prepared solution of 0.5% resorcinol in concentrated HCl. A visible
red complex will form quickly with ketoses and more slowly with aldoses.
a. Draw fructose and identify the three alcohol
functional groups involved in the dehydra-
tion reactions necessary to convert fructose
into hydroxymethylfurfural.
HO
O
b. Draw the mechanism for each (one of them includes an enol tautomeriza-
tion reaction!).
Transcribed Image Text:3. The Seliwanoff Test tests for ketoses by forming hydroxymethylfurfural (shown below) when heated with a strong mineral acid. This compound forms a red complex with resorcinol (1,3-dihydroxybenzene). The Seliwanoff reagent is a freshly prepared solution of 0.5% resorcinol in concentrated HCl. A visible red complex will form quickly with ketoses and more slowly with aldoses. a. Draw fructose and identify the three alcohol functional groups involved in the dehydra- tion reactions necessary to convert fructose into hydroxymethylfurfural. HO O b. Draw the mechanism for each (one of them includes an enol tautomeriza- tion reaction!).
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