CHEM 2332H Lecture : Lecture 522014.pdf
15 Jul 2014
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Can apply fischer in a lot of places. *w/ these themes, more challenging mechanism can be reduced to analogy to foundational ones. Acyl substitution under basic conditions (protonate later, not first) pka is important here. -usually primary halogens are the worst electrophile that still works. If under acid, do e1 (e1cb: for conjugate baseenolate then elimination) Acetoacetate & malonic ester synthesis ok w/ some secondary halides. Key step in acid hydrolysis of malonic esters & acetoacetate esters = loss of carbon dioxide. Ochem page 5 tautomer other cases that don"t fit here like bh3like of like hvz case. After step 1: identify the carbon in acetone as electrophile, identify the 2 carbon in di-ester as nucleophile, identify that we"re in base: substitute alpha to carbonyl should involve enolates. We"re in base --> deprotonate to make a better nucleophile. Ochem page 6 can"t be the ester on bottom has to be top ester group: identify acyl substitution to get cyclic intermediate.
