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The weakest acid (does not show acidic c...

The weakest acid (does not show acidic character) is:

A

`HC-=CH`

B

`CH_(2)=CH_(2)`

C

`Me_(3)CH`

D

`Ph_(3)CH`

Text Solution

AI Generated Solution

The correct Answer is:
To determine the weakest acid among the given options, we need to analyze the stability of the anions produced when each acid ionizes. The stability of the anion is crucial because a more stable anion corresponds to a stronger acid. ### Step-by-Step Solution: 1. **Understanding Acidity**: - Acidity is related to the stability of the anion formed after the acid donates a proton (H+). The more stable the anion, the stronger the acid. 2. **Analyzing the First Compound (Ethyne, CH≡CH)**: - Upon ionization, ethyne produces HC≡C⁻ (an anion). - The carbon in the anion is sp-hybridized, which has higher electronegativity compared to sp² or sp³ hybridized carbons. - Therefore, the anion is relatively stable, indicating that ethyne is an acidic compound. 3. **Analyzing the Second Compound (Ethene, CH₂=CH₂)**: - Ethene ionizes to produce CH₂=C⁻ (an anion). - The carbon in this anion is sp²-hybridized, which is less electronegative than sp-hybridized carbon. - Thus, the anion is less stable than that of ethyne, but still shows some acidic character. 4. **Analyzing the Third Compound (tert-Butyl anion, (CH₃)₃C⁻)**: - This compound ionizes to produce a carbanion with three methyl groups attached. - The presence of three electron-donating methyl groups increases the electron density on the anion, making it less stable. - Therefore, this compound is expected to be the least acidic. 5. **Analyzing the Fourth Compound (Triphenylmethane, (C₆H₅)₃C⁻)**: - This compound ionizes to produce a carbanion that is stabilized by resonance due to the three phenyl groups. - The resonance stabilization makes this anion very stable, indicating that this compound is a strong acid. 6. **Conclusion**: - Comparing the stability of the anions produced from all four compounds, the weakest acid is the one that produces the least stable anion. - The weakest acid, which does not show significant acidic character, is (CH₃)₃C⁻ (the tert-butyl anion). ### Final Answer: The weakest acid (does not show acidic character) is (CH₃)₃C⁻ (tert-butyl anion).
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