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

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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.

**Explanation of Diagram:**

- The chemical structure shown is of an anthocyanidin at pH 3. 
- There is a benzopyrylium cation with a hydroxyl group adjacent to the pyran ring.
- The diagram illustrates that upon deprotonation (removal of H⁺) at higher pH, resonance structures may form which should be depicted in the labeled boxes.
  
**Tasks:**

- Box labeled "first resonance structure here": Draw the first stable resonance form at pH 7.
  
- Box labeled "second resonance structure here": Draw the second stable resonance form at pH 7.

Make sure to include any lone pairs and formal charges, and use curved arrows to illustrate electron movement between structures.
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. **Explanation of Diagram:** - The chemical structure shown is of an anthocyanidin at pH 3. - There is a benzopyrylium cation with a hydroxyl group adjacent to the pyran ring. - The diagram illustrates that upon deprotonation (removal of H⁺) at higher pH, resonance structures may form which should be depicted in the labeled boxes. **Tasks:** - Box labeled "first resonance structure here": Draw the first stable resonance form at pH 7. - Box labeled "second resonance structure here": Draw the second stable resonance form at pH 7. Make sure to include any lone pairs and formal charges, and use curved arrows to illustrate electron movement between structures.
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