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.

b. Chemical structure of an ester featuring a phenyl group and a cyclohexyl group connected by an ester linkage.

Accepted Answer

Hi, everybody. Welcome back. Our next question says, determine the products that would result from the complete acid catalyzed hydrolysis of phenyl acetate. We have four different answer choices with four different possibilities. And we'll look at each of those once we think about what is going on in this reaction. So we have acid klise hydrolysis of an ester. We can tell by looking at the name, that's what we have. And when we look at estra names, we know esters are formed by the condensation reaction between an alcohol and a carboxylic acid. So we can hydrolyze our ester and regenerate those two things. However, with a slight difference, when we have acid catalyzed hydrolysis, there's lots of protons around. We regenerate the carboxylic acid in its acid form. If we had base catalyzed reaction, we would instead have a carboxylate, an iron in those basic conditions. So just something to keep in mind when we think about the products that we would generate when we're hydroly an ester. So when we look at an astro name, we can actually figure out the answer to this just by looking at its name, the first word. So fennel would be the alcohol. So the r group of the alcohol and the acetate reflects the parent acid. So in this case, Fenny means our alcohol was spinal. So a phel group with an O, so we draw our benzene ring with an O age group attached and our parent acid, we have the name with the ending eight. So it would be acidic acid if the and eight ending is acetate. So, acetic acid is just ach three attached to a carbon carbon and then oh in the acidic form, because we have acid catalyzed hydrolysis. And just so that we keep clear what's going on. When we think about the mechanism of this, our original Esther would have had our ch three group attached to the carbon carbon and that carbon carbon is attached to an oxygen, which then in this case would have been attached to our benzene ring. Excuse this sort of weird appearance of that benzene ring. And the bond that would have been broken in the hydrolysis would be between the carbon carbon and the oxygen that would be reacting with water in water. The bond would have been broken between the oh and one of the hydrogens, the lone pairs on the fennel or what would be phenol on that oxygen will pick up the proton and the electrons on the oh minus will react with that carbonyl carbon to form reform the carboxylic acid. So that's where the bond is breaking to regenerate these products. So now let's look at our answer choices to determine which is correct. In choice. A our carboxylic acid is not correct. We have two methyl groups on that carbonyl carbon. So this is incorrect. That should be, this is a ketone. You should have C three on one side and oh on the other, our second product is also incorrect because we do not, don't have a benzene ring. We have a carbon chain with two double bonds and two alcohol groups. So that's not what we want there. We need phenol as our product choice. B, we don't have a carboxylic acid. We have a dye alcohol here. We have ach three attached to a carbon with 20 groups. So that's incorrect. And we don't have pol or we don't have phenol. Excuse me, we have an open up ring. So a carbon chain with two double bonds and two carbonel bonds. So we actually have a di aldehyde here and Choice B. So that's incorrect to C we do have acetic acid correctly indicated and phenol, so it looks like to C is our answer to be thorough. We'll look at choice D in choice D, our acetic acid is in the form of and acetate an ion has that O minus instead of oh which should only form in basic conditions. And our phenol instead of being phenol has an H2O plus. So that's not going to be the product. We would just want it to be an oh group. So this shows the hydrogens of water uh assorting incorrectly to our product. Our rea our products, excuse me, the choice D is incorrect. So once again, the products that would form from the complete acid catalyse hydrolysis of Fenty ay. This choice C acetic acid and phenol. See you in the next video.

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

Key Concepts

Acid-Catalyzed Hydrolysis

Esters

Reaction Mechanism

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