When d-glucose is treated with an aqueous bromine solution (buffered to a pH of 6), an
Chapter 24, Problem 24.81(choose chapter or problem)
When d-glucose is treated with an aqueous bromine solution (buffered to a pH of 6), an aldonic acid is formed called d-gluconic acid. Treatment of d-gluconic acid with an acid catalyst produces a lactone (cyclic ester) with a six-membered ring. (a) Draw the structure of d-gluconic acid. (b) Draw the structure of the lactone formed from d-gluconic acid, showing the configuration at each chirality center. (c) Would you expect this lactone to be optically active? (d) Explain how you would distinguish between the d-gluconic acid and the lactone using IR spectroscopy
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