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Exercise · Q30

Q.Compare the acidic character of ethyne, ethene and ethane, giving the reason based on percentage ss-character.

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Ethyne's acidic hydrogen sits on an spsp-hybridised carbon (50%50\% ss-character), ethene's on an sp2sp^2-hybridised carbon (33%33\% ss-character), and ethane's on an sp3sp^3-hybridised carbon (25%25\% ss-character). Since an ss orbital's electron density is held, on average, closer to the nucleus than a pp orbital's, a hybrid orbital with more ss-character behaves as though the carbon holding it is more electronegative, so the lone pair left on the carbanion after deprotonation is held more tightly and stabilised more effectively the higher the ss-character of the orbital it occupies. A more stabilised conjugate base corresponds directly to a stronger acid, so acidity runs in the same order as ss-character: ethyne (spsp, pKa≈25\text{p}K_a \approx 25) is the most acidic, followed by ethene (sp2sp^2 …

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