F3C I OH Br3C III Rank the compounds (shown below) in order of increasing acidity. H3C OH II SOH A) | < ||| < || B) ||| < || < | C) || < ||| < | D) ||| < | < || E) || < I < |||

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**Ranking the Compounds in Order of Increasing Acidity**

Given the compounds below, determine the order of increasing acidity.

**Compounds:**

- **Compound I:** Consists of a carboxyl group (COOH) with a trifluoromethyl substituent (CF₃) attached to the carbon atom. This compound is labeled as I: \( F_3C-COOH \).

- **Compound II:** Contains a carboxyl group (COOH) with a methyl substituent (CH₃) attached to the carbon atom. This compound is labeled as II: \( H_3C-COOH \).

- **Compound III:** Comprises a carboxyl group (COOH) with a tribromomethyl substituent (CBr₃) attached to the carbon atom. This compound is labeled as III: \( Br_3C-COOH \).

**Options for Ranking:**

A) I < III < II

B) III < II < I

C) II < III < I

D) III < I < II

E) II < I < III

**Explanation:**

The acidity of carboxylic acids depends on the electron-withdrawing or electron-donating nature of the substituent attached to the carboxyl carbon. Electron-withdrawing groups stabilize the negative charge on the conjugate base, increasing the acid strength, while electron-donating groups decrease the acid strength.

- **Compound I (CF₃-COOH)** has a strongly electron-withdrawing trifluoromethyl group.
- **Compound II (CH₃-COOH)** has a weakly electron-donating methyl group.
- **Compound III (CBr₃-COOH)** has a strongly electron-withdrawing tribromomethyl group, but less so than the trifluoromethyl group.

Therefore, the order of increasing acidity generally follows the electron-withdrawing ability:
\[ \text{II} < \text{III} < \text{I} \]

**Correct Answer:**

C) II < III < I
Transcribed Image Text:**Ranking the Compounds in Order of Increasing Acidity** Given the compounds below, determine the order of increasing acidity. **Compounds:** - **Compound I:** Consists of a carboxyl group (COOH) with a trifluoromethyl substituent (CF₃) attached to the carbon atom. This compound is labeled as I: \( F_3C-COOH \). - **Compound II:** Contains a carboxyl group (COOH) with a methyl substituent (CH₃) attached to the carbon atom. This compound is labeled as II: \( H_3C-COOH \). - **Compound III:** Comprises a carboxyl group (COOH) with a tribromomethyl substituent (CBr₃) attached to the carbon atom. This compound is labeled as III: \( Br_3C-COOH \). **Options for Ranking:** A) I < III < II B) III < II < I C) II < III < I D) III < I < II E) II < I < III **Explanation:** The acidity of carboxylic acids depends on the electron-withdrawing or electron-donating nature of the substituent attached to the carboxyl carbon. Electron-withdrawing groups stabilize the negative charge on the conjugate base, increasing the acid strength, while electron-donating groups decrease the acid strength. - **Compound I (CF₃-COOH)** has a strongly electron-withdrawing trifluoromethyl group. - **Compound II (CH₃-COOH)** has a weakly electron-donating methyl group. - **Compound III (CBr₃-COOH)** has a strongly electron-withdrawing tribromomethyl group, but less so than the trifluoromethyl group. Therefore, the order of increasing acidity generally follows the electron-withdrawing ability: \[ \text{II} < \text{III} < \text{I} \] **Correct Answer:** C) II < III < I
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