Predict the product of the following series of reactions.

Question

(a) Chemical reaction diagram showing a benzene derivative with reagents for side-chain oxidation and product prediction.

Accepted Answer

All right. Hi, everyone. So for this question, lets go ahead and identify the final products formed in the series of reactions shown below. Here, we have our starting material, one sec butle four tuttle bez reacting first with potassium permanganate, hydroxide and heat. And then in the second step with isopropyl alcohol and H two. So four. So if I scroll down here, I have four different answer choices labeled A through D. So lets go ahead and get started. Now, in this case, because we have a series of two different reactions, we have to consider each one step by step. So on the bottom of the screen, I went ahead and I redrew or starting material. So in the first step, I'm going to go ahead and consider the first reaction in my series, right. So on the screen, I read through one sec bel four turpal benzene and I'm first going to react this compound with potassium permanganate km four in the presence of hydroxide and heat. Now, let's go ahead and talk about what this reaction is going to entail. Now, our starting material is an ocho benzene. We've got a benzene ring with oche substituents and the reagent combination of potassium permanganate and hydroxide is if you recall a very strong, powerful oxidizing agent. So, not only is this a strong oxidizing agent, we're also introducing very harsh conditions for this reaction because of the presence of a high heat. So recall that this is going to be the oxidation reaction of an O benzi. Now recall that an oxidation reaction involves two different things because when we talk about an oxidation reaction, we discuss two different definitions, either there's an increase in bonds between carbon and hetero atoms or there is a decrease in bonds between carbon and hydrogen. So in the case of this reaction, if there is at least one benzo carbon hydrogen bond, then that benzo carbon is going to be converted into a carboxylate ion. And because these, these reaction conditions are so harsh, the length of the ocho group does not actually matter. So recall the benzo position refers to a carbon atom, an oteo carbon atom directly attached to a benzene ring. So in this case, I have two ben delic positions. I have one from the TP beetle group and another from the sect beetle group. Now, the benthic carbon of my turpal group actually has no hydrogen atoms attached. So this position cannot be oxidized. However, the carbon atom or the Belic carbon atom of the seburo group does in fact have one hydrogen. So the benic carbon from the sec beal group is going to be oxidized into a carboxylate ion. So this means that the remaining carbons from the sec beetle substituent are going to be removed entirely because these conditions are so harsh. So, in this case, for the product of the first step of the reaction, I'm going to first draw my benzene ring which remains intact. And I'm also going to go ahead and redraw my torpedo group which was not oxidized. But instead of redrawing my sec beal substituent, I'm going to go ahead and draw a carboxylate ion instead on that position. So that gives me my final product of the first step, which is four T Betty benzoate. Now recall that this type of oxidation reaction produces a carboxylic acid only after acid is added to proton the resulting ion. But now that we have our carboxylate ion, we can introduce our second step. And our second step involves taking her carboxylate ion reacting that with isopropyl alcohol and also in the presence of H two. So four. So now notice how in the second step of our series here, we have a carboxylate ion reacting with an alcohol in acidic conditions. If you recall, the second step of this reaction is going to involve Fisher S stir education in which we are going to produce an ester in water as a by product. So in this case, the isopropyl group of isopropyl alcohol is going to install itself onto the oxygen here of the carboxylate ion that has a negative charge. So I'm going to bring those two things together to create my Esther. So here's my benzene ring with my torpedo group and now attached to my carboxylate oxygen is an isotopy group and we have water here as a by-product. But because the question is requesting only the organic final product, what I'm going to highlight is our ether here which is isopropyl or tery benzoate. So here is our final organic product. And so if I consider the answer choices that we saw in the beginning, our answer is going to be option D in the multiple choice and there you have it. So the following series of reactions was first an oxidation to produce a carboxylate ion followed by a Fisher ester application process to produce an ester. And so with that being said, if you stuck around until the end of this video, I thank you so very much for watching and I hope you found this helpful.

Predict the product of the following series of reactions.
(a)

Key Concepts

Side-Chain Oxidation of Alkylbenzenes

Chromic Acid Oxidation

Esterification Reaction

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