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Example · Example 3

Q.Explain why the carbonyl carbon of an aldehyde or ketone is electrophilic, using the polarity of the C=O\text{C=O} bond and the hybridisation of the carbon.

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The carbonyl carbon is sp2sp^2 hybridised, forming three coplanar σ\sigma bonds at ≈120∘\approx 120^\circ and one π\pi bond to oxygen from its remaining unhybridised pp orbital. Because oxygen is considerably more electronegative than carbon, it attracts the π\pi (and to a lesser extent σ\sigma) bonding electrons more strongly, leaving the oxygen with a partial negative charge (δ−\delta^-) and the carbon with a matching partial positive charge (δ+\delta^+). This can be represented by a minor charge-separated resonance form, C+-O−\text{C}^+\text{-O}^-, alongside the major neutral C=O\text{C=O} form.

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The planar, sp2sp^2 carbonyl carbon carries a partial positive charge because the more electronegative oxygen pulls the π\pi electron density towards itself, making the carbon electron-deficient and open to nucleophilic attack from either face.

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