Q.Explain the following: Acidic nature of Alkyne OR Explain the following: Anti-Markownikoff rule
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Start your 14-day free trial to unlock the full solution →Terminal alkynes are weakly acidic because their terminal C-H bond is unusually polar, due to the high s-character of the sp-hybridised carbon.
In a terminal alkyne (a triple bond with at least one H directly attached to a triple-bonded carbon, e.g. HC triple bond C-R), the carbon bearing that hydrogen is sp-hybridised. sp orbitals have 50% s-character (compared to 33% for sp2 in alkenes, and 25% for sp3 in alkanes). Since s-orbitals hold electron density closer to (and more tightly bound by) the nucleus than p-orbitals do, a carbon with more s-character is more electronegative — it holds the C-H bonding electrons more tightly toward itself, making that C-H bond significantly more polarised (carbon delta-negative, H delta-positive) than a C-H bond on an sp3 or sp2 carbon.
This increased polarity means the hydrogen on a terminal alkyne carbon can be removed as H+ more readily than hydrogens elsewhere in the molecule — this is the basis of the (weak) acidic character of terminal alkynes. Evidence for this acidity:
- Terminal alkynes react with strong bases like sodium amide (NaNH2) to form sodium acetylides, releasing H2: HC triple bond CH + NaNH2 gives HC triple bond C-Na+ + NH3. …
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