Predict the products and propose mechanisms for the following rea...

Question

Predict the products and propose mechanisms for the following reactions. (a)

Accepted Answer

Hey, everyone, let's do this problem. It says predict the products or product for the following reaction and propose a mechanism. So we have an ester reacting with an acid, right H plus is an acid. And that will make this reaction an acid catalyzed Esther hydraulic sis and the products of that type of reaction are a carb oxalic acid and an alcohol. Okay. So we're actually knowing what the structure of a carb oxalic acid looks like we have a C double bond o single bonded to O H, right? So our carb oxalic acid is basically going to be this half of the molecule and then the rest of the compound, these last three carbons in this group will turn into an alcohol group. Okay. So let's get started with the mechanism, I'll redraw or reactant. So the first step since we are existing in an acid, right, our oxygen, our carbonell oxygen that has some lone pairs is going to be predominated by the acid like so which will result on or sorry result in a positive charge on the oxygen now. Okay. So there are some resonance structures that you can have here with this structure. This positive charge, one of those would include a positive charge on this carbon in a single bond to the oxygen. Okay. So knowing that this carbon also sort of has a partial positive charge. It makes sense that in the next step, this water that we are in is going to attack the pro native carbonell group at the carbon to form a tetrahedron intermediate. So we have our O H group that was originally there and then we just added our water. So now this oxygen has a positive charge. Okay. So with the positive charge on this oxygen, it's looking to get rid of a proton, right? So this neighboring oxygen Is actually going to d protein eight from the water group. Okay. So we're sharing those protons all around to all the oxygen atoms. So now this oxygen has a positive charge. All right. So that makes this a good leaving group. So one of the alcohol groups is going to swing its electrons down toward that carbon, kicking off this chunk to form an alcohol, which is one of our products, 1, 2, 3 carbons. So there's our alcohol and then we're left with and almost car bucks of the acid, except this oxygen has a proton, right? We had two alcohol groups. Now we have one alcohol group and we just need to get rid of this proton on the carbonell group. So that water, since we're in acidic conditions, we'll come back take this hydrogen to give us our carb oxalic acid. Oops, what is that? Just making up my own stuff now? So we have our Quebec silic acid and then each 30 plus from that water. That was just, that just deep resonated our compound. So we have our carb oxalic acid and our alcohol and this is our whole mechanism which makes d the correct answer for this problem. That's it for this one. I hope this video was helpful and thanks for watching.

Predict the products and propose mechanisms for the following reactions. (a)

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