Anthocyanin is a naturally occurring compound that acts as a pigment in many fruits and vegetables. At low pH values (<3), it exists as the cation shown below and exhibits a bright red color. At higher pH values (~7), it exhibits a purple-ish color. As the pH is raised from pH 3 to pH 7, one of the hydroxyl groups can be deprotonated (the H* that is removed has been circled for you) to produce the corresponding resonance stabilized neutral compound. Draw the two most stable resonance structures for this anthocyanin at pH 7. Make sure to explicitly show all non-bonding lone pairs and formal charges where appropriate. Include curved arrows to show how you got from the first resonance structure to the other. first resonance strucure here OH НО. -[sugar] H OH Structure of anthocyanidine at pH 3 H+ second resonance structure here

Organic Chemistry
8th Edition
ISBN:9781305580350
Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Publisher:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Chapter4: Acids And Bases
Section: Chapter Questions
Problem 4.48AP: As we shall see in Chapter 19, hydrogens on a carbon adjacent to a carbonyl group are far more...
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Connections to biology
Anthocyanin is a naturally occurring compound that acts as a pigment in many fruits and vegetables. At low
pH values (<3), it exists as the cation shown below and exhibits a bright red color. At higher pH values (~7), it
exhibits a purple-ish color. As the pH is raised from pH 3 to pH 7, one of the hydroxyl groups can be
deprotonated (the H* that is removed has been circled for you) to produce the corresponding resonance
stabilized neutral compound. Draw the two most stable resonance structures for this anthocyanin at pH 7.
Make sure to explicitly show all non-bonding lone pairs and formal charges where appropriate. Include curved
arrows to show how you got from the first resonance structure to the other.
first resonance strucure here
OH
HO.
-[sugar]
H
OH
Structure of anthocyanidine at pH 3
H+
second resonance structure here
Transcribed Image Text:Connections to biology Anthocyanin is a naturally occurring compound that acts as a pigment in many fruits and vegetables. At low pH values (<3), it exists as the cation shown below and exhibits a bright red color. At higher pH values (~7), it exhibits a purple-ish color. As the pH is raised from pH 3 to pH 7, one of the hydroxyl groups can be deprotonated (the H* that is removed has been circled for you) to produce the corresponding resonance stabilized neutral compound. Draw the two most stable resonance structures for this anthocyanin at pH 7. Make sure to explicitly show all non-bonding lone pairs and formal charges where appropriate. Include curved arrows to show how you got from the first resonance structure to the other. first resonance strucure here OH HO. -[sugar] H OH Structure of anthocyanidine at pH 3 H+ second resonance structure here
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