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☢ Deux profs de chimie en prison !? ☢ Quelle chimie dans Breaking Bad (2/n) ?


What? 2 chemistry teachers arrested for making meth at university in Arkansas? ♪ "Breaking Bad" credits ♪ Hello chemists! Okay, today, a little special video We'll talk about : news, current events, drugs, organic synthesis So you may have heard of it on November 15, we have 2 chemistry colleagues who were arrested in an American state, Arkansas, because they are suspected of synthesizing a very very hard drug, (S) N-methyl-1-phenyl- propan-2-amine So you probably know it because in fact her known name is methamphetamine

So methamphetamine chemically, it's very close to amphetamine There is just an additionnal methyl group, so one CH₃: 1 carbon and 3 more hydrogens But one CH₃ changes everything, because this drug is much harder, much more devastating than amphetamine So let's be clear chemists, this video is not intended to judge those 2 teachers Besides, they haven't gone to court yet, so uh Who knows What interests us is the chemistry behind it So, little tutorial for methamphetamine No, seriously we’re just going to do it on paper, because I don't want to end up in jail, and obviously I will not show you how to make meth, but We're going to revise organic chemistry a little bit

Come on, let's go, fasten your belts Let's go Good chemists, let's start by talking about the methamphetamine molecule In fact, this molecule exists in 2 forms, which are mirror images of each other, a bit like your hands: my left hand is the mirror image of my right hand but I can't overlay them In short, without going into detail, let's say that I represent these 2 molecules, placing all the hydrocarbon part in the plane of your screen

The nitrogen atom can go: either backwards or forwards And it turns out that these 2 molecules called enantiomers do not have the same biological properties For the cook who seeks to synthesize his drug, methamphetamine one must get only one of these 2 molecules, and it turns out that this is where the nitrogen atom on your screen, is positioned backwards The other molecule will not have the desired activity, and that is very important for what follows

So what betrayed our 2 colleagues? Well, we measured particularly high levels of benzyl chloride in their laboratory And benzyl chloride, it can be used to synthesize a lot of stuff, but also methamphetamine Good, chemists, before talking about the famous synthesis that our colleagues could have made from benzyl chloride, I already suggest that we resume the 2 syntheses presented in the Breaking Bad series So, the 1st synthesis, it takes place from pseudoephedrine Pseudoephedrine, I put the diagram here, it's this molecule, and you can get methamphetamine by reduction I had already presented this synthesis in the recent episode which I made on Breaking Bad and the reduction will be done thanks to the red phosphorus, in the presence of iodine And besides, we had seen that the scene with phosphine gas, it was phony, etc

I draw your attention to a very important point: the advantage of synthesis with pseudoephedrine, is that the carbon that carries the nitrogen atom is already in the right configuration That is to say, you see the nitrogen atom on your screen, it's backwards, and suddenly, it will ask less work for chemists Finally, we just have to reduce an alcohol group So it's a pretty simple synthesis It's it's art! No, it's chemistry, uh

very basic Walt, carbon 1, it carries the alcohol group, and carbon 2, it carries the amine group So these are 2 asymmetric carbons that we have in pseudoephedrine

Do you have another question? Well in this synthesis with pseudoephedrine, the alcohol group is reduced to an alkane, and we preserve the amine so very clearly, we eliminate asymmetric carbon n° 1 and we keep asymmetric carbon n° 2 That's it, chemists, for the 1st synthesis So I hope you understand it, the big advantage of synthesis with pseudoephedrine, is that we already have carbon who has the right configuration with the nitrogen atom well positioned, and which allows to arrive only to the right form of methamphetamine Now in the series if you remember correctly, at one point, well they have they have more pseudoephedrine They therefore turn to a second synthetic route from P2P P2P is phenyl-2-propanone

So to make this synthesis, we're going to do what's called a reductive amination So now how does reductive amination work? I'll make it short, but basically it is done in 2 steps: in a 1st step, we will make an addition methylamine on P2P So 2-phenyl-propanone which will lead us to an imine Besides, remember in the series, at least 2 times, They have to steal enough stocks important methylamine, precisely And then this imine, we're going to reduce it to a secondary amine

So there are lots of possible conditions for reduction there I do not go into detail, but this synthesis will pose a problem because in fact when reducing you are going to get the 2 enantiomers of methamphetamine, so the 2 forms I told you about at the beginning and that's not interesting because we have: one of the forms that has the desired biological activity, but the other of the forms which is useless So finally, it's like we have 50% of loss And Walt, he talks about this problem elsewhere

Listen to him So technically, he said something stupid In reality, we need a stereoselective synthesis here and not stereospecific But you know what ? I want to detail this synthesis a little more so, for those who want to go further in chemistry or higher education students, I remind you that I have a secondary channel, so I’m making a video where I’m detailing the mechanism a little bit, reductive amination, and I explain a little better to you steroselectivity / sterospecificity I close the parenthesis

And we make a little summary: the reductive amination, uh interesting synthesis But we have to add

uh a technique for have a stereoselective synthesis and therefore get the right molecule at the end I think that with regard to the 2 syntheses of the Breaking Bad series, we’re pretty good, and now I suggest you come back, uh to the problem of our 2 colleagues and their benzyl chloride

Well chemists, now we have benzyl chloride Chloride Benzyl chloride

Benzyl chloride And from benzyl chloride, we have to switch to methamphetamine Bah already what I propose: we're not going to break our heads too much Benzyl chloride, we just have to convert it to P2P, and as we already know how to transform P2P methamphetamine by reductive amination, it's over Now chemistry students, I count on you: to pause there, and suggest me in the comments, please play the game

Suggest in the comments a P2P synthesis route from benzyl chloride Of course, several answers are possible Okay, while you are making your proposals, huh, I'm going to read a little Ah well, NADH / NAD + co-enzyme We’re going to talk about it chemists soon, huh

Okay, is that good? You made me your proposals in the comments? I will read them carefully So How can we do ? Well, I want to tell you: we want to create a carbon-carbon bond, since we need to lengthen the carbon chain For that, normally, you should know that one of the most effective means, – at least within the framework of current higher education programs – is to go through a mixed organomagnesium We offer transform benzyl chloride in benzylmagnesium chloride, and then after that we can make it react cold with an equivalent of acetic anhydride, and normally we come to P2P

Ok students, for synthesis with acetic anhydride I explain it to you on my secondary channel And you will see that in fact: it's not on the agenda, but it should be there because, here it is: it's interesting Uh well, it's time to conclude I want to say that like any self-respecting chemistry teacher, I'm a huge fan of the Breaking Bad series, but however, I don't want to start doing meth I wanted to wish you all, well a very happy new year 2020 Don't take too many good resolutions because anyway, we never stick to them Don't drug yourself, that's it

And then as always, thank you again for your confidence, huh Thanks to everyone who, who follow the adventures of Blablareau at the lab, remember if you want chemistry more daily, you can follow me on Instagram, Facebook, Twitter, and for those who want to support the creation of our videos, You can find us on Tipee, and UTip, And as for me, I tell you soon

in the lab !

Source: Youtube

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