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To chapter 20, problem number 63 from the mcmurray organic chemistry textbook.
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This problem tells us that carboxylic acids having a second carbonyl group, two atoms away, can lose carbon dioxide through an intermediate enolate ion when treated with base.
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And so we are asked to draw the mechanism by which this reaction is going to proceed.
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Okay, so the first thing that's going to happen here is going to be deprotonation.
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And so the base molecule is going to accomplish that.
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And so that is going to look like this.
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And so we will then have this intermediate, so this carboxylate ion.
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And so one of the lone pairs on this carboxylate ion is going to add.
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In here, form a double bond.
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This carbon -carbon bond is going to break, and these electrons are going to go right here.
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And one of the carbon -oxygen bonds, those electrons will kick up to this oxygen.
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So after this step, that's when we form the enolate that the problem mentions...