Rank the following compounds in order of increasing acidity, and explain your ranking. -СООН -СООН Br E A A O₂N B COOH (least acidic) < C (most acidic) COOH The strongest acid has a strong electron-withdrawing group base. The weakest acid has a strong electron-donating group H₂C that will D B destabilize that will stabilize the E COOH Dositive D the negative charge in its conjugate charge in its

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Chapter1: Chemical Foundations
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**Ranking Compounds in Order of Increasing Acidity**

**Compounds:**
- **A:** Bromobenzoic acid
- **B:** Nitrobenzoic acid
- **C:** Methoxybenzoic acid
- **D:** Methylbenzoic acid
- **E:** Benzoic acid

**Order of Increasing Acidity:**
- **E (Benzoic acid) (least acidic) < C (Methoxybenzoic acid) < B (Nitrobenzoic acid) < D (Methylbenzoic acid) < A (Bromobenzoic acid) (most acidic)**

**Explanations:**

1. **The strongest acid**:
   - Has a **strong electron-withdrawing group** which **destabilizes** the **positive** charge in its conjugate base.

2. **The weakest acid**:
   - Has a **strong electron-donating group** which **stabilizes** the **negative** charge in its conjugate base.

This is crucial in understanding the influence of various substituents on the acidity of benzoic acid derivatives.
Transcribed Image Text:**Ranking Compounds in Order of Increasing Acidity** **Compounds:** - **A:** Bromobenzoic acid - **B:** Nitrobenzoic acid - **C:** Methoxybenzoic acid - **D:** Methylbenzoic acid - **E:** Benzoic acid **Order of Increasing Acidity:** - **E (Benzoic acid) (least acidic) < C (Methoxybenzoic acid) < B (Nitrobenzoic acid) < D (Methylbenzoic acid) < A (Bromobenzoic acid) (most acidic)** **Explanations:** 1. **The strongest acid**: - Has a **strong electron-withdrawing group** which **destabilizes** the **positive** charge in its conjugate base. 2. **The weakest acid**: - Has a **strong electron-donating group** which **stabilizes** the **negative** charge in its conjugate base. This is crucial in understanding the influence of various substituents on the acidity of benzoic acid derivatives.
Expert Solution
Step 1

For a carboxylic acid,

Electron withdrawing group enhances the acidity of the carboxylic acid

Electron donating group decreases the acidity of the carboxylic acid.

Among the given, -NO2 is the strongest Electron withdrawing group. So, B is the most acidic one.

-OCH3 is the strongest Electron donating group. So, C is the least acidic.

The order is 
C (least acidic) < D < A < E < B (most acidic)

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