Acid_cat_hydrolysis0

Acid_cat_hydrolysis0 - transfer HO OH O O NH 2 HO CO 2 H HO...

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A student asks: 2005 test #3 part C…how do the EtO's turn into OH? Could you draw me an electron pushing solution? 3F too if you don’t mind. .. EtO OEt O O NaOEt H EtO OEt O O O OEt EtO OEt O O OEt O EtOH EtO OEt O O OEt O EtO OEt O O OEt O H 3 O EtO OEt O O OEt O H OH 2 EtO OEt HO O OEt O OH 2 proton transfer EtO OEt HO O OEt O OH H EtO OH OH O OEt O –EtOH H 2 O EtO O OH O OEt O same acid- catalyzed hydrolysis HO O O O OH O – 2EtOH H heat –CO 2 decarboxylation HO O OH O Michael reaction of the easily-accessible enolate Acid-catalyzed ester hydrolysis, followed by decarboxylation
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Here’s 3F, as requested: EtO OEt O O NaOEt N EtO OEt O O Alkylation of the easily-accessible enolate O O N O O R Br EtO OEt O O N O O acid-catalyzed ester hydrolysis, as above HCl, H 2 O HO OH O O N O O H 3 O HO OH O O N O O H H 2 O HO OH O O N OH O OH then proton transfer H HO OH O O N HO HO O H HO OH O O N HO H CO 2 H proton transfer H 2 O HO OH O O N HO H CO 2 H H 2 O proton
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Unformatted text preview: transfer HO OH O O NH 2 HO CO 2 H HO HO OH O O NH 2 + CO 2 H OH HO H 2 O CO 2 H CO 2 H O OH O O NH 3 O O NH 3 H heat, decarboxylation final product from this point is an arrow-pushing mechanism for acid-mediated hydrolysis of a phthalimide I'm not showing it, but this reaction is undoubtedly aided by the presence of carboxylic acid groups that can protonate intramolecularly . Indeed, the final cleavage step may well happen intramolecularly to give phthalic anhydride, which would then be ring-opened by water to give the dicarboxylic acid byproduct shown....
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Acid_cat_hydrolysis0 - transfer HO OH O O NH 2 HO CO 2 H HO...

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