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If a nucleophile is to attack the above compound, how do I determine wheather it kick the chlorine atom out via an SN2, or will it attack the electron deficient carbonyl?

Does it depend on the nucleophile used? If yes, please explain the variations I can expect if I am to expose the above compound to a range of nucleophiles (strong, weak, etc.) Does the solvent also play a role here? Pretty confused.

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  • $\begingroup$ Like everything synthetic chemistry it depends on the conditions. With a harder, more basic nucleophile you can also deprotonate and eliminate HCl to give acrolein which will do 1,4 additions - equivalent to attack on the Cl, just not directly $\endgroup$ – Waylander Jan 12 at 8:07

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