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Quinine, found in tonic water, is shown below. Identify the most acidic proton from choices, I-V. .IV H 1 но. H-ZO `N H || = ||| NG ケレ

Quinine, found in tonic water, is shown below. Identify the most acidic proton from choices, I-V. .IV H 1 но. H-ZO `N H || = ||| NG ケレ

Chemistry
Chemistry
10th Edition
ISBN:9781305957404
Author:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Publisher:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Chapter1: Chemical Foundations
Section: Chapter Questions
Problem 1RQ: Define and explain the differences between the following terms. a. law and theory b. theory and...
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**Determine the most basic Nitrogen atom in this structure:** The diagram provided is a chemical structure with several labeled hydrogen atoms (H) attached to nitrogen atoms (N+), marked with roman numerals I, II, III, IV, and V. Underneath the structure, there are multiple-choice options: A) I B) II C) III D) IV E) V Please select the hydrogen atom that is attached to the most basic nitrogen atom in the structure.
Transcribed Image Text:**Determine the most basic Nitrogen atom in this structure:** The diagram provided is a chemical structure with several labeled hydrogen atoms (H) attached to nitrogen atoms (N+), marked with roman numerals I, II, III, IV, and V. Underneath the structure, there are multiple-choice options: A) I B) II C) III D) IV E) V Please select the hydrogen atom that is attached to the most basic nitrogen atom in the structure.
### Organic Chemistry Exercise: Analyzing Quinine **Quinine, found in tonic water, is shown below. Identify the most acidic proton from the choices I–V.** #### Molecular Structure of Quinine ![Quinine Structure](quinine_structure.jpg) This diagram shows the molecular structure of quinine, with certain protons labeled as I, II, III, IV, and V. The structural features include: - A quinoline ring system on the left. - A vinyl group (-CH=CH2) extending from the right side of the structure. - A methoxy group (OCH3) and an alcohol group (OH). - Two nitrogen atoms, one in the ring structure and one in a bridgehead position. **Choices for the Most Acidic Proton:** - **I:** Proton attached to the hydroxyl group (-OH). - **II:** Proton attached to the nitrogen of the quinoline ring. - **III:** Proton attached to the nitrogen of the bridgehead. - **IV:** Proton attached to the terminal carbon in the vinyl group. - **V:** Proton attached to the methine group (carbon adjacent to a double bond). #### Answer Choices: - **A) I** - **B) II** - **C) III** - **D) IV** - **E) V** When evaluating the acidity of protons in a molecule, factors such as the stability of the conjugate base after deprotonation, resonance stabilization, and inductive effects must be considered. An acidic proton is typically one whose removal yields a stable conjugate base. ### Explanation of the Most Acidic Proton: To solve for the most acidic proton in quinine, let's analyze each position: 1. **Proton I (OH Group):** The hydroxyl group can donate a proton to form a resonance-stabilized phenoxide ion, which can make this proton relatively acidic. 2. **Proton II (NH Group):** Protons attached to nitrogen can be relatively acidic due to the nitrogen's ability to stabilize the negative charge. 3. **Proton III (Bridgehead NH):** Similarly, this proton would be somewhat acidic due to nitrogen stabilization but may be less accessible. 4. **Proton IV (Vinyl CH):** A vinyl proton tends to be less acidic because removing this proton does not lead to significant resonance stabilization. 5. **Proton V (Methine CH):** This proton is also less acidic compared
Transcribed Image Text:### Organic Chemistry Exercise: Analyzing Quinine **Quinine, found in tonic water, is shown below. Identify the most acidic proton from the choices I–V.** #### Molecular Structure of Quinine ![Quinine Structure](quinine_structure.jpg) This diagram shows the molecular structure of quinine, with certain protons labeled as I, II, III, IV, and V. The structural features include: - A quinoline ring system on the left. - A vinyl group (-CH=CH2) extending from the right side of the structure. - A methoxy group (OCH3) and an alcohol group (OH). - Two nitrogen atoms, one in the ring structure and one in a bridgehead position. **Choices for the Most Acidic Proton:** - **I:** Proton attached to the hydroxyl group (-OH). - **II:** Proton attached to the nitrogen of the quinoline ring. - **III:** Proton attached to the nitrogen of the bridgehead. - **IV:** Proton attached to the terminal carbon in the vinyl group. - **V:** Proton attached to the methine group (carbon adjacent to a double bond). #### Answer Choices: - **A) I** - **B) II** - **C) III** - **D) IV** - **E) V** When evaluating the acidity of protons in a molecule, factors such as the stability of the conjugate base after deprotonation, resonance stabilization, and inductive effects must be considered. An acidic proton is typically one whose removal yields a stable conjugate base. ### Explanation of the Most Acidic Proton: To solve for the most acidic proton in quinine, let's analyze each position: 1. **Proton I (OH Group):** The hydroxyl group can donate a proton to form a resonance-stabilized phenoxide ion, which can make this proton relatively acidic. 2. **Proton II (NH Group):** Protons attached to nitrogen can be relatively acidic due to the nitrogen's ability to stabilize the negative charge. 3. **Proton III (Bridgehead NH):** Similarly, this proton would be somewhat acidic due to nitrogen stabilization but may be less accessible. 4. **Proton IV (Vinyl CH):** A vinyl proton tends to be less acidic because removing this proton does not lead to significant resonance stabilization. 5. **Proton V (Methine CH):** This proton is also less acidic compared
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