Chemistry
Chemistry
10th Edition
ISBN: 9781305957404
Author: Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Publisher: Cengage Learning
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**Title: Ranking Protons by pKa in a Molecular Structure**

**Objective:**
Determine the order of the labeled protons in terms of increasing pKa values for the given molecule.

**Structure:**
The molecule features the following elements:
- An ether group to the left, connected to a cyclopentane ring.
- The cyclopentane ring is bonded to an oxygen atom with a double bond.
- Attached to the ring are two different groups:
  - **Ha:** Located on the ether oxygen.
  - **Hb:** Attached to the cyclopentane ring near the oxygen.
- A side chain extending from the ring contains:
  - Fluorine atom bonded to a methine group.
  - Connected to this group is:
    - **Hc:** Near the fluorine atom.
  - An additional ester functional group characterized by:
    - A carbonyl oxygen and methoxy group.
    - **Hd:** Hydrogen on the methoxy group.

**Task:**
Rank the protons (Ha, Hb, Hc, Hd) according to increasing acid dissociation constant (pKa). Lower pKa values indicate stronger acidity.

**Instructions:**
1. Analyze the electron-withdrawing and donating effects of surrounding atoms or bonds.
2. Consider the influence of functional groups on each hydrogen's acidity.
3. Complete the ranking by evaluating which protons are more acidic (lower pKa).

**Diagram:**
[Molecular structure with labeled protons including labeled hydrogen atoms and details on chemical bonds.]

**User Input Section:**
Allows input for pKa ranking:
- Respond by selecting the checkbox next to an answer box.
- Provide the order of protons based on pKa values.

**Tools:**
- [ ] Option to reset input
- Navigation arrows to adjust page view

**Outcome:**
Understanding the molecular environment's influence on proton acidity enhances your grasp of organic chemistry concepts related to functional groups and their reactivity.
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Transcribed Image Text:**Title: Ranking Protons by pKa in a Molecular Structure** **Objective:** Determine the order of the labeled protons in terms of increasing pKa values for the given molecule. **Structure:** The molecule features the following elements: - An ether group to the left, connected to a cyclopentane ring. - The cyclopentane ring is bonded to an oxygen atom with a double bond. - Attached to the ring are two different groups: - **Ha:** Located on the ether oxygen. - **Hb:** Attached to the cyclopentane ring near the oxygen. - A side chain extending from the ring contains: - Fluorine atom bonded to a methine group. - Connected to this group is: - **Hc:** Near the fluorine atom. - An additional ester functional group characterized by: - A carbonyl oxygen and methoxy group. - **Hd:** Hydrogen on the methoxy group. **Task:** Rank the protons (Ha, Hb, Hc, Hd) according to increasing acid dissociation constant (pKa). Lower pKa values indicate stronger acidity. **Instructions:** 1. Analyze the electron-withdrawing and donating effects of surrounding atoms or bonds. 2. Consider the influence of functional groups on each hydrogen's acidity. 3. Complete the ranking by evaluating which protons are more acidic (lower pKa). **Diagram:** [Molecular structure with labeled protons including labeled hydrogen atoms and details on chemical bonds.] **User Input Section:** Allows input for pKa ranking: - Respond by selecting the checkbox next to an answer box. - Provide the order of protons based on pKa values. **Tools:** - [ ] Option to reset input - Navigation arrows to adjust page view **Outcome:** Understanding the molecular environment's influence on proton acidity enhances your grasp of organic chemistry concepts related to functional groups and their reactivity.
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