Predict the major products of treating the following compounds...

Question

Predict the major products of treating the following compounds with hot, concentrated potassium permanganate, followed by acidification with dilute HCl.

(a) isopropylbenzene

(b) p-xylene

(c)

Accepted Answer

Hey everyone and welcome back. What are the major oxidation products expected when the following compounds are treated with hot basic. But as in permanganate and then acidified with hydrochloric acid that is the absolute. Now we're given three compounds. But before we begin solving this problem, let's just understand the general reaction sequence. Now, let's suppose that you have a benzene ring and suppose that we have a side chain with an L kill group are in particular, we're dealing with a side chain oxidation for this reaction. We need the following set of regions just as described in the problem. First of all, step, number one is addition of potassium permanganate in a strong basic solution so that we are going to include hydroxide as well as heat right now, for number two, we are going to use, let's suppose hydrochloric acid. We want to use a strong asset which is a proton donor. Now, essentially in the welfare step, we're going to produce our color box late and ion. And the reason why we need to use a strong asset is to make sure that we protein ate it into an asset. So what you're going to do, you're going to identify your Benz Ilic carbon and you're going to eliminate all of the rest of your side chain and turn that Ben's Ilic carbon into carbon cilic acid. So the general reaction scheme would look as follows you're just going to turn that Ben's Ilic carbon into a carb oxalic acid group. Once again in the first step, we're getting our car box late and in the second step, we are protein. Ating it into an asset. It doesn't really matter how long your chain is. We are always getting one carbon atom immediately. We get our asset at the first men's Ilic carbon. So the problem becomes really simple. If we start with a we have to Halloween, we can throw the structure of Halloween which corresponds to benzene ring with a metal group bonded to it. So we understand that this is our zilla carbon. Right? And we are going to turn that Ben zilla carbon into carbon oxalic acid group. Let's once a game include our regions. So that would be number one. But as in permanganate in a basic solution, Addition of heat number two hydrochloric acid. According to the problem. We're using dilute solutions. We can also include dilute. Okay, and we can see the same in our modal equation. So as we said before, we are going to redraw the benzene ring from the left side and we are going to turn that carbon into a car book silic acid. So we're going to get Ben's OIC acid. That's the first product that we get. So let's label this is our answer to part A and we are ready to move on to part B. You may simply redraw the starting with cereal. Similarly, we have our benzene ring, But now it's bonded to a five member drink. Okay, so that's our five. Number grain 12312345. Okay, so what we want to do, we want to once again think About the sequence of our reaction. # one addition of potassium permanganate in a strongly basic solution Which is hot. And number two edition of hydrochloric acid dilute. We identify our Ben zilla carbons. There are two meaning the side chain oxidation will take place at each of these carbon atoms. We're going to break apart the remaining fragment which corresponds to our alcohol group. Right? So if we just break it apart and we understand that we have to be in zilla carbons, we're going to oxidize each of them into an asset. So the structure for our product would look as follows. We have our benzene ring first wall and we're going to turn this first carbon atom into a car broke cilic asset group and we will perform exactly the same steps over here on the adjacent carbon atom we get our curb oxalic acid as well. So that's our product for B. Let's label this is our final answer for B. And let's continue with the third one. We have Ortho xylene. Let's recall that Ortho xylene essentially means that or generally is Eileen means that you have two metal substitutions bonded to your benzine ring because it's Ortho. It basically means that the two metal substitutions are worth with respect to each other. So if you add one metal substitution over here at the top, the adjacent position is Ortho. So you can add another metal group adjacent to this one because they're Ortho with respect to each other. So that's Ortho xylene. And from here we are just going to use our set of regions That would be number one potassium permanganate in a strongly basic solution which is hot. And # two edition of dilute hydrochloric acid. Because we have to Ben zilla carbons over here in blue were going to turn each of them into a car bookseller Kassid group. So we are ready to draw our product. We may simply draw benzene ring and you may notice that we don't get the same product we will get one card oxalic acid group and the adjacent one just as in power bi. So we can draw it in the same orientation. For simplicity. Right suppose that this is our metal group which is now turned into a car, broke cilic asset and then at the adjacent position we have our other curb oxalic acid group. And that would be it. We got our product for part C. Let's label this is our final answer. And basically we can just stay that for this problem. We had to recall the side chain oxidation whenever you have an L kill group bonded to your benzene ring and whenever you use but as simple magnate in basic solution which in the presence of heat followed by the addition of hydrochloric acid or a strong asset which will be dilute. Generally you're going to turn your Benz Ilic carbon or basically the world first carbon that is bonded to your benzine ring into a cab oxalic acid, breaking apart all of the rest of your alcohol group. That's what we saw in Part B, right. We essentially had to break apart this fragment and we only took into account our Benzali carbons. In each case we are turning our benzel, a carbon atoms into carbon silicon acid groups. And that's it. Based on our answer, we may conclude that the correct answer to the multiple choice question is C Thank you for watching.

Predict the major products of treating the following compounds with hot, concentrated potassium permanganate, followed by acidification with dilute HCl.
(a) isopropylbenzene
(b) p-xylene
(c)

Key Concepts

Oxidation Reactions

Potassium Permanganate (KMnO4) as an Oxidizing Agent

Acidification with Dilute HCl

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