HW5_N_Key - CH 2 O NaOH (aq) HO Intramolecular Aldol...

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Last Name: UTEID: First Name: SCORE: KEY Deadline for CH310N HW 5, Due: Oct 17 3:00 PM 2,6-Diketones can be cyclized to form cyclohexenones, through a series of equilibrating intermediates. Propose a mechanism for the example below. Show all important flows of electrons, charges and intermediates. Where indicated, (in the structure boxes)- draw the intermediates.
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Unformatted text preview: CH 2 O NaOH (aq) HO Intramolecular Aldol Formation of an enolate O H 3 C CH 3 O O CH 3 H O CH 2 O H 2 O CH 3 O HO-alkoxy-ketone O CH 3 O H H OH Continue on next page Box #3 heat OH-hydroxy-ketone-alkoxy-ketone Proton transf er (f rom water) Dehydration Final Product O CH 3 O H H OH O CH 3 OH H O H 2 O This is the same box #3:...
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This note was uploaded on 10/24/2011 for the course CH 310n taught by Professor Iverson during the Spring '08 term at University of Texas at Austin.

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HW5_N_Key - CH 2 O NaOH (aq) HO Intramolecular Aldol...

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