When considering the acidic strength of hydrocarbons, which reaction intermediate is formed that dir — GOC and Organic Chemistry Basics Chemistry Question
Question
When considering the acidic strength of hydrocarbons, which reaction intermediate is formed that directly dictates the relative acidity of ethyne ($HC\equiv CH$) compared to ethene ($CH_2=CH_2$)?
Answer: C
💡 Solution & Explanation
Acidic strength depends on the stability of the conjugate base. Ethyne loses a proton to form the ethynyl carbanion ($HC\equiv C^-$), which is $sp$ hybridized. The high s-character (50%) stabilizes the negative charge better than the $sp^2$ carbanion from ethene, making ethyne more acidic.
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