1. The molecule below is ascorbic acid, also known as vitamin C. a. As drawn below, ascorbic acid is shown as a diketone. An enol tautomer of ascorbic acid exists and is how the molecule is usually drawn. Draw the enol tautomer of ascorbic acid. b. Show the mechanism for tautomerization under basic conditions from the ketone to the enol. c. Ascorbic acid has a pKa of 4.6 which is more similar to that of a carboxylic acid than an alcohol. Which H is most acidic in ascorbic acid? d. Explain why Vitamin C is so acidic. OH OH ascorbic acid OH

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1. The molecule below is ascorbic acid, also known as vitamin C.
a. As drawn below, ascorbic acid is shown as a diketone. An enol tautomer of
ascorbic acid exists and is how the molecule is usually drawn. Draw the
enol tautomer of ascorbic acid.
b. Show the mechanism for tautomerization under basic conditions from the
ketone to the enol.
c. Ascorbic acid has a pK₂ of 4.6 which is more similar to that of a carboxylic
acid than an alcohol. Which H is most acidic in ascorbic acid?
d. Explain why Vitamin C is so acidic.
OH
OH
ascorbic acid
OH
Transcribed Image Text:1. The molecule below is ascorbic acid, also known as vitamin C. a. As drawn below, ascorbic acid is shown as a diketone. An enol tautomer of ascorbic acid exists and is how the molecule is usually drawn. Draw the enol tautomer of ascorbic acid. b. Show the mechanism for tautomerization under basic conditions from the ketone to the enol. c. Ascorbic acid has a pK₂ of 4.6 which is more similar to that of a carboxylic acid than an alcohol. Which H is most acidic in ascorbic acid? d. Explain why Vitamin C is so acidic. OH OH ascorbic acid OH
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