Aspartame, the sweetener used in the commercial products Nutra...

Question

Aspartame, the sweetener used in the commercial products NutraSweet and Equal, is 200 times sweeter than sucrose. What products will be obtained if aspartame is hydrolyzed completely in an aqueous solution of HCl?

Chemical structure of aspartame, a sweetener, labeled with its name in blue text.

Accepted Answer

Hello everyone. So in this video, we're talking about the derivative of a known sweetener and we're given the structure here. So this big molecule here will undergo a complete hydrolysis in a delude solution of H C L. So, because we're mentioning H C L here, we are still being under acidic conditions because of this, we're dealing with a acid catalyzed hydrolysis reaction. All right. So of this whole entire compound, the only two functional groups that can actually undergo this reaction is going to be our amide group as well as our group. All right. So let's go ahead and actually copy some of the general mechanisms that already drew for our groups and our amide groups when they're going under this acid cally hydrolysis reaction. So again, these are just general mechanisms but they will help us in determining our final products. All right. So starting off with our ester functional group, we can see here because we're going under acid conditions. Our first step will always be a pro step. So we can go ahead and grab a proton from our acid. And then we see that this carbon carbon becomes very electrolytic. So the H O will act as a nuclear file and attack at this electrolytic site. So then we get our tetrahedron intermediate and we have the deportation of our H2O group and the lone pair or the bond between the oxygen and hydrogen will become a lone pair on this oxygen making it another alcohol group. Then the pairs on auction here will grab a proton of pro nation step again. And then we know that carbon Neals like to reform. So from our top alcohol group, we have the lone pairs coming down to form a pi bond. And essentially, we get back the carbon neal group and we are left with an alcohol group. So we see that our, our group does actually leave and then we have just in alcohol at the end. All right. Now, moving on to the amide functional group. So same thing we are under acidic condition. So the first step will always be a pronation step. So we see that we have a pronation from our acid and we're using our lone pairs from our oxygen to grab this proton. We get a positive charge on the alcohol group or the O H group. Now, because we have lost a lone pair. Now again, the carbon carbon is extra electrolytic. So the H O will come in as a nuclei and attack again, we have a de step of our H2O group. And then we get another tetrahedron intermediate. But this time, the lone pairs on the nitrogen will go ahead and perate itself. And we can see here that basically the following three steps are exactly the same. We do have a leaving group of N H three here. And of course, we can see that the A two has left and we were left with an alcohol group instead. So we can see here that most of the art groups are going to leave and they eventually just become an O H group. So now if we go back to the region here, let's go ahead and actually erase the circles for the functional groups that, that we already know that ester and amides here will go ahead and undergo this acid cally. So we can see which our groups, we're going to go ahead and actually cleave out. So we can see that the R group on our group is this on the left here. So we can go ahead and cleave that bond as well as our amide. We can see we have a cleaving over here. All right. So we can see then that we get three different segments in this big molecule. And those are going to be our three products in this reaction. Straw reaction arrow there. All right. So one of the products, the smallest product that we get is over to the left. So we get these three carbons and then an alcohol group. And of course, this, as we can see is an alcohol group. So that's one of our products. And then this one in the middle here, let's go ahead and draw that one out. So we have, of course, the six membered ring here with alternating pie buns. Then we have the alcohol group, of course, then we have a carbonyl group and then we have a N H three group and this N H three group, of course, has a plus one thermal charge because we have a quinary amine, we have three bonds to the hydrogens and then we have one bond to the carbon. And then the last and final product is going to be the right side of our molecule. So, of course, again, we have a alcohol group, then we have a Carboni group. And over to the right here, we have a nitrogen group with two methyl groups attached. And all the way at the end, we have another alcohol group and carbonyl group. So we see here at the terminal ends of our third product, we have coo H groups over to the right and left and slightly in the middle, we have the nitrogen here with the two methyl groups. Let's actually bring those a little bit closer. All right. So we can see here that we do get three total products here. And this all comes from this derive of a sweetener that undergoes a acid callis hydrolysis. So let's go ahead and highlight our three products because that's going to be our final answer for this problem.

Aspartame, the sweetener used in the commercial products NutraSweet and Equal, is 200 times sweeter than sucrose. What products will be obtained if aspartame is hydrolyzed completely in an aqueous solution of HCl?

Key Concepts

Hydrolysis

Aspartame Structure

Acid-Catalyzed Reactions

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