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mechanism

Was going through my notes and realised I didn't completely fill them in. The first few steps I think are quite self-explanatory but I'm really confused about the last step where I go from the five-membered ring to the final product by adding water.

I'd be really grateful if someone could clear this up or provide any suggestions!

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  • $\begingroup$ Does this related reduction help? $\endgroup$
    – user55119
    Commented Mar 19 at 17:57

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The last step represents the hydrolysis of the organometallic ring aduct during the acidic work-up of the reaction. This hydrolysis might proceed via deprotonation of a water molecule (or hydronium ion) by the carbon atom bonded to aluminium, since it holds a negative charge density (carbon is more electronegative than aluminium - https://pubchem.ncbi.nlm.nih.gov/ptable/electronegativity/). Aluminium will then be converted to Al(OH)3 as the oxygen atom is also protonated.

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