8) Rank the following protons (lubelco HD) in order of decreasing acidity Explain using ARIO

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...
icon
Related questions
icon
Concept explainers
Question
**Educational Website Text:**

**Ranking the Acidity of Protons:**

**Question:**
Rank the following protons (labeled H\_A, H\_B, H\_C, H\_D) in order of decreasing acidity. Explain using ARIO principles.

**Explanation with Diagram:**

The chemical structure provided depicts a heterocyclic compound with labeled protons: H\_A, H\_B, H\_C, and H\_D. The task is to rank these protons based on their acidity using the ARIO framework.

**Diagram Explanation:**
- The structure includes an indole-like ring attached to a bicyclic system.
- Each proton label (H\_A, H\_B, H\_C, H\_D) corresponds to different positions on the molecule, indicating where these protons are attached.
- The ARIO method stands for:
  - **A**tom: Consider the atom to which the hydrogen is attached. More electronegative atoms stabilize negative charge better.
  - **R**esonance: Evaluate whether the conjugate base is stabilized by resonance.
  - **I**nductive Effect: Consider electron-withdrawing or -donating groups.
  - **O**rbital: Analyze the hybridization state of the atom bearing the negative charge after deprotonation.

**Application of ARIO:**
1. **Atom:** Examine which atom the proton is connected to and assess its electronegativity and ability to stabilize negative charge.
2. **Resonance:** Check if resonance structures can stabilize the conjugate base.
3. **Inductive Effect:** Identify any functional groups that might enhance acidity through electron-withdrawing effects.
4. **Orbital:** Consider the hybridization of the atom and how this impacts the acidity.

To determine the order of acidity, compare each proton using these criteria. The more stable the conjugate base, the more acidic the proton. Provide a detailed explanation based on these observations.

**Note:** Further experimental data or computational chemistry methods may be required for a precise ranking.
Transcribed Image Text:**Educational Website Text:** **Ranking the Acidity of Protons:** **Question:** Rank the following protons (labeled H\_A, H\_B, H\_C, H\_D) in order of decreasing acidity. Explain using ARIO principles. **Explanation with Diagram:** The chemical structure provided depicts a heterocyclic compound with labeled protons: H\_A, H\_B, H\_C, and H\_D. The task is to rank these protons based on their acidity using the ARIO framework. **Diagram Explanation:** - The structure includes an indole-like ring attached to a bicyclic system. - Each proton label (H\_A, H\_B, H\_C, H\_D) corresponds to different positions on the molecule, indicating where these protons are attached. - The ARIO method stands for: - **A**tom: Consider the atom to which the hydrogen is attached. More electronegative atoms stabilize negative charge better. - **R**esonance: Evaluate whether the conjugate base is stabilized by resonance. - **I**nductive Effect: Consider electron-withdrawing or -donating groups. - **O**rbital: Analyze the hybridization state of the atom bearing the negative charge after deprotonation. **Application of ARIO:** 1. **Atom:** Examine which atom the proton is connected to and assess its electronegativity and ability to stabilize negative charge. 2. **Resonance:** Check if resonance structures can stabilize the conjugate base. 3. **Inductive Effect:** Identify any functional groups that might enhance acidity through electron-withdrawing effects. 4. **Orbital:** Consider the hybridization of the atom and how this impacts the acidity. To determine the order of acidity, compare each proton using these criteria. The more stable the conjugate base, the more acidic the proton. Provide a detailed explanation based on these observations. **Note:** Further experimental data or computational chemistry methods may be required for a precise ranking.
Expert Solution
Step 1

HAH++A-

The acidity of a molecule (HA) depends on the stability of the conjugate base (A-).

This can be determined via ARIO rule

The stability of the -ve charge on the conjugate base depends on the following four factors.
1. The type of atom that carries the charge (A): Size and electronegativity of the -ve charge-carrying atom. Greater the size of the atom, the more stable the -ve charge. Similarly greater the electronegativity of the atom, the more stable the conjugate base. 
2. Resonance (R): Resonance stabilizes the -ve charge by delocalization. Hence greater the chance for such resonance, the more stable the conjugate base. 
3. Induction (I): Induction can also stabilize the -ve charge on the conjugate base by spreading it out.
4.  The type of orbital where the charge resides (O): Shorter the size of the atomic orbital where the electron pair is residing, the greater its stability.

These factors construct the acronym, ARIO. While comparing the acidity of protons, we generally use ARIO as
the order of importance of these stabilizing effects.

steps

Step by step

Solved in 2 steps with 1 images

Blurred answer
Knowledge Booster
Ionic Equilibrium
Learn more about
Need a deep-dive on the concept behind this application? Look no further. Learn more about this topic, chemistry and related others by exploring similar questions and additional content below.
Recommended textbooks for you
Chemistry
Chemistry
Chemistry
ISBN:
9781305957404
Author:
Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Publisher:
Cengage Learning
Chemistry
Chemistry
Chemistry
ISBN:
9781259911156
Author:
Raymond Chang Dr., Jason Overby Professor
Publisher:
McGraw-Hill Education
Principles of Instrumental Analysis
Principles of Instrumental Analysis
Chemistry
ISBN:
9781305577213
Author:
Douglas A. Skoog, F. James Holler, Stanley R. Crouch
Publisher:
Cengage Learning
Organic Chemistry
Organic Chemistry
Chemistry
ISBN:
9780078021558
Author:
Janice Gorzynski Smith Dr.
Publisher:
McGraw-Hill Education
Chemistry: Principles and Reactions
Chemistry: Principles and Reactions
Chemistry
ISBN:
9781305079373
Author:
William L. Masterton, Cecile N. Hurley
Publisher:
Cengage Learning
Elementary Principles of Chemical Processes, Bind…
Elementary Principles of Chemical Processes, Bind…
Chemistry
ISBN:
9781118431221
Author:
Richard M. Felder, Ronald W. Rousseau, Lisa G. Bullard
Publisher:
WILEY