Q.(a) Explain acidic nature of Ethyne with suitable examples.
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Start your 14-day free trial to unlock the full solution →(a) Terminal alkyne H is weakly acidic due to high s-character of the sp carbon; (b)(i) Cl2 addition to propene gives 1,2-dichloropropane; (b)(ii) Hg2+/H2SO4-catalysed hydration of propyne gives acetone.
(a) Acidic nature of ethyne: In ethyne (HC triple-bonded to CH), each carbon is sp hybridised (50% s-character), which is a much higher proportion of s-character than sp2 (33%, alkenes) or sp3 (25%, alkanes) carbons. Because s-orbitals hold electron density closer to the nucleus, the electrons in an sp C-H bond are held more tightly/closer to carbon, making the sp carbon effectively more electronegative and the terminal C-H bond more polarised, so the terminal hydrogen can be removed as H+ more easily than an sp2/sp3 C-H. This weak acidity is demonstrated experimentally:
- HC≡CH + 2Na -> NaC≡CNa + H2 (up) (sodium acetylide, liberates H2 gas)
- Ethyne + ammoniacal AgNO3 -> white precipitate of silver acetylide, Ag-C≡C-Ag
- Ethyne + ammoniacal Cu2Cl2 -> red precipitate of copper acetylide, Cu-C≡C-Cu
Alkanes and alkenes, lacking this acidic terminal hydrogen (or having much lower s-character), do not show these reactions.
(b)(i) CH3-CH=CH2 + Cl2: This is a simple electrophilic addition of chlorine across the C=C double bond of propene, adding one Cl to each alkene carbon:
CH3-CH=CH2 + Cl2 --> CH3-CHCl-CH2Cl (1,2-dichloropropane)
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