Draw the products you would obtain from acid-catalyzed hydroly...

Question

Draw the products you would obtain from acid-catalyzed hydrolysis of the following esters.

a. Isopropyl benzoate

Accepted Answer

Hi, everybody. Our next problem says, draw the products that would be formed when ethyl acetate is subjected to acid catalyzed hydrolysis. So with that name ethyl acetate that tells us that we are talking about an ester. And when we hydroly an ether, we regenerate our carboxylic acid by hydroly it by adding a water molecule to form the ester, we had a condensation reaction. So to form the ether, we had a condensation reaction of a carboxylic acid and an alcohol. So we can hydrolyze our ether and a water molecule to regenerate those two. Now, another important key here is, it says acid catalyzed. And that's key because when we think about carboxylic acids, we know they're weak acids and they can exist in their acid form or in their basic form, their carboxyl ion form. So if we have an acid catalyzed hydrolysis, so, acid catalyzed, we expect the product to be the carboxylic acid since we have excess hydrogen ions around if we have a base catalyzed reaction, which is called a saponification, that means our carboxylic acid instead of being its acid form, it will be in the form of a carboxylate. And I am because in basic conditions, you wouldn't expect it to be sitting around in the acidic form. But we have acid catalyzed hydrolysis. So we're going to be regenerating the carboxylic acid. So we actually don't even need to fool around with mechanisms or anything like that because the very name of our era tells us what the initial reactants were. The name of an ester consists of the our group from the alcohol and then the parent acid with the ending eight rather than OIC acid. So our name Ethel acetate of our Esther tells us that the original alcohol was ethanol and the parent acid was acetic acid. So the product of an acid catalyze hydrolysis will be acetic acid, which is CH three. So just that methyl group, then our carbon group C double Bruno and oh and our ethanol is a two carbon alcohol. So ch three, CH two and then, oh, our answer choices are in line structures. So I have drawn the line structures as well. So we have our alcohol and our parent acid that formed our Esther. So let's look at our answer choices to see which is correct. When we look at choice. A, we see we indeed have acetic acid and ethanol. So right away, we have our correct answer to be thorough though. Lets look at our other answer choices. Choice B our carbonel group has ch three groups on either end. So this is not acetic acid. This is a ketone, not an the carboxylic acid at all. So this is a ketone. So we're going to go ahead and cross that out. And indeed, when we look at our other product that has a carbon carbon with an oh and nothing, this is formic acid. So choice B doesn't have either product. Correct. Choice C shows us as the first product, an ester not a carboxylic acid, we have ach three co double bond bonded to an oxygen and then ACH three group. So this seems to show the bond breaking in the middle of the ethyl branch, which is not what would happen. So that's incorrect. And then it shows the alcohol being the oh group and ACH three. So that shows the bond breaking in the wrong place. Let's recall that if we look at our original um ester that's being hydrolyzed since it's from acetic acid, we have ach three group, a carbonyl carbon, then that carbon carbon is bound to an oxygen which then has an athol branch on it. So our products in choice C would be as if you broke the bond between the in the middle of the ethanol, which is not what's happening here. When we hydrolyze this ester, we are breaking the bond between the carbon and carbon and the oxygen that is going to be part of the alcohol. Then an oh group from the water, a hydroxy ion will be added to the carbon carbon. And a proton will be added to the oxygen of the al to generate the alcohol. So twice C, in correct choice D gives us ch three C, double B turn O and then just an O. Well, we have, we would have an acetate anion that would be generated in basic conditions. But, and it would just have its oxygen here, but it would be negatively charged. And again, that would only be in basic conditions. So this is incorrect because we should have a hydrogen there since we're in acidic conditions. This also shows instead of ethanol, it has two hydrogens on the oxygen. So that's incorrect to just be oh on the end of that ethanol. So that's incorrect. It shows the hydrogens going in the wrong place on our products. So once again, the product form when ethyl acetate is subjected to acid catalyze hydrolysis is choice a acetic acid and ethanol. See you in the next video.

Struggling with GOB Chemistry?

Draw the products you would obtain from acid-catalyzed hydrolysis of the following esters.

a. Isopropyl benzoate

Watch next

Ester Reactions: Acid-Catalyzed Hydrolysis practice set

Struggling with GOB Chemistry?

Draw the products you would obtain from acid-catalyzed hydrolysis of the following esters.a. Isopropyl benzoate

Watch next

Ester Reactions: Acid-Catalyzed Hydrolysis practice set

Draw the products you would obtain from acid-catalyzed hydrolysis of the following esters.

a. Isopropyl benzoate