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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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.
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](/v2/_next/image?url=https%3A%2F%2Fcontent.bartleby.com%2Fqna-images%2Fquestion%2F468a1036-9eac-47e7-b3af-5f844e8c7d46%2F92f386a2-e1e2-477e-b3c6-eca4fc669c18%2Fsv340i_processed.jpeg&w=3840&q=75)
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
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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