Which of the following hydrocarbons is exceptionally acidic (compared to standard alkanes or alkenes β GOC and Organic Chemistry Basics Chemistry Question
Question
Which of the following hydrocarbons is exceptionally acidic (compared to standard alkanes or alkenes) because the loss of its proton yields a highly stable, aromatic conjugate base?
Answer: C
π‘ Solution & Explanation
Cyclopentadiene ($C_5H_6$) readily loses a proton ($H^+$) from its $sp^3$ hybridized carbon to form the cyclopentadienyl anion ($C_5H_5^-$). This anion is planar, fully conjugated, and possesses $6\ \pi$ -electrons, making it aromatic and thus providing a massive thermodynamic driving force for the deprotonation.
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