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 < |||
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 < |||
Chemistry for Today: General, Organic, and Biochemistry
9th Edition
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Author:Spencer L. Seager, Michael R. Slabaugh, Maren S. Hansen
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Chapter13: Alcohols, Phenols, And Ethers
Section: Chapter Questions
Problem 13.61E
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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](/v2/_next/image?url=https%3A%2F%2Fcontent.bartleby.com%2Fqna-images%2Fquestion%2F80575cd1-5db7-410a-9515-d71a86ac864c%2Fe0752056-a592-42c2-987e-9f1cfec25ffc%2F8p94k19_processed.jpeg&w=3840&q=75)
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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