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Attempt:

I did aldol condensation in acidic medium followed by $\ce{E1cB}$ to get 1,3-diphenylbut-2-enone but the answer given is:

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I am unable to devise a mechanism to reach the above product from the reactant. Could someone please suggest the mechanism?

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  • $\begingroup$ Do another aldol onto the ketone of your 1,3-diphenylbut-2-enone $\endgroup$
    – Waylander
    Nov 5, 2018 at 12:46

2 Answers 2

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I have drawn a three step mechanism as opposed to the concerted step reaction proposed in the other answer.

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This mechanism has the added benefit of not leaving any room for formation of any side products as there is only one source carbon of acidic hydrogens in each compound.

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The only mechanism I see is, you write the three molecules in enol form (acidic medium) and try to form a cyclic compound in a concerted step as you did in forming benzene from acetylene and then as it is acidic medium, you gotta eliminate water molecules from the new cyclohexane to end up at the product.

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