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Day 2: Synthesis and Chemiluminescence of an Oxalate EsterWe will be synthesizing the oxalate ester from methyl salicylate and oxalyl chloride in the presence of a ...

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Day 2: Synthesis and Chemiluminescence of an Oxalate EsterWe will be synthesizing the oxalate ester from methyl salicylate and oxalyl chloride in the presence of a non-nucleophilic base in what is a textbook addition-elimination reaction_ Because oxalyi chloride is a di-acid halide, there will be two consecutive addition-elimination reactions

Day 2: Synthesis and Chemiluminescence of an Oxalate Ester We will be synthesizing the oxalate ester from methyl salicylate and oxalyl chloride in the presence of a non-nucleophilic base in what is a textbook addition-elimination reaction_ Because oxalyi chloride is a di-acid halide, there will be two consecutive addition-elimination reactions



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As discussed in Are You Wondering $27-2,$ carbocation rearrangements occur in some substitution and elimination reactions. What elimination product would you expect in the following reaction if no rearrangement ofthe carbocation occurs? Experiment reveals that the main product is 2,3 -dimethyl- 2 -pentene. Suggest a mechanism that shows how 2,3 -dimethyl- 2 -pentene is formed. [Hint: Consider the formation and rearrangement of a carbocation.]

You're asked to predict the product that would result from a carbon cattle and shift not occurring and suggested mechanism for the carbon cat island shift occurring. So we're starting with two Barimo three metal fencing, reacting with water. So we have secondary alcohol load. We have a polar partick solvent. So because of these two conditions, we it can be either s and one or e one. But we're told the major product was the one, but they had the same carbon cat on intermediate. The first step is for the alcohol had to leave giving us a secondary car. Park it on. So if no rearrangement were, they were they were to occur. The water would grab a hydrogen here and for me, not keen right there. So we know this. It wouldn't form a double bond here because this relieved to five bombs. So we have a mono substituted Arkin we brought with us bound to some our group. So it's always better to have an internal a keen or to have more substitutes if we redraw it with the the shift. We have a metal shift where the metal goes where one method goes with a carbon cat iron was, and it changes place with the the card account on. So we have this. We don't have a tertiary carbon cat on as opposed to secondary, and this is more stable because it has, um, more substitue. It's that act as electron donating groups that help stabilize the car back out on. But Russia is always more stable than secondary, and secondary is more stable than primary, so water then grabs this hydrogen. It's more accessible and forms anarchy in earlier giving us this and can redraw with this so we have more substitue. It's making it more stable because they can, um, stabilize the R key. But it's always better to have more substitutes and internal hockey and results from a metal shift.

Hillary want whoever during chapter 23 poems 60 forints from ass to drug to different hallow ketones are conformed a bi intra molecular calculation reaction and be synthesized a using issue acidic as your servicer Solis Servan s o the service. The hallow key tone. So we didn't just start with a very simple one. It's one Brahmin. Then we see that we have to add this entire our group. But we already have intellectual found here. So we need to make this carbon good fall. So that way we can do is make that into a cranium so we can add and g b are so green arid regions. And then this counter number carbons and you want to answer We have 123 for five, and then six carbon. And then we have these six here on the side of the sixth car. That was not a blown me so first thing first What I react Thes tool. This is the car Bannon's do a new cliff look attack of this position. So what we're gonna be left with is something that looks like this. And now if I add in some sort of strong base So I'm a dockside deep. Only the alpha proton here deformity estimate carbonite and witching goes through an essence who stepwise essence to a neutral flick Attack at this carbon Electra filler. Carbon here to kick off roaming to now form the final product like this. So this is one way in no way is that you can actually make pull through these carbon nuclear Philip by having both the mounds of green, your region so and DVR and junior. And then you're going to react that with now your key tone. But now I'm gonna have to heroes. So then you're gonna have to nickel files attacking the carbon with your tool. You're leaving groups. So then right away, in one step, you'll get your final product. This reaction will be very messy. Go Wouldn't really recommend Doing this in the lab is because you are very minimal control about what else can go on this reaction. But is that to ask possibilities form for using the conditions provided in the question of Halki tone But apart being us to do from the cereal asio acid acidic acid S s s s so sorry. From where asio acidic acid um we start from the estrogen being thiss, and now we have a strong base. Sorry, it's oxide and they weren't at our electro file. There's even be the carbons that we need to answer all of these carbons here. We'll see home of drawing it. That kind of little resembles the shape that I want. So it is easier to count carbons that way. So after one equivalence of this reaction, we'll have reacted one of these Elektra files. So we make our man, and I'll hit one of these electoral Filic carbon centers to form this. And then if I reacted with another equivalent of space sort of meth oxide, you make deep only the other second. But Proton proton here to form the carbon in which can then go threats into backside attack to give us this product here like this. And now, if I at an acidic water and heat, you get spontaneous Deke remarks, elation and hide dialysis off our Esther. Just leave our Qi Tian plus years

To its mechanism Problem starting with this very long s there. We have sodium at dockside, Of course. Access your bass. So in this case, we can actually form the late all the way at this terminal raffle. We're going to have a lot of the Cascade Oven electron movement to this conjugated. You know, late Now, at this point, we can react with our die asshole Aqsa late at the terminal. Karpin at this point will actually kick off this ATHOC side group, and we will generate little bond here. Total bond here. New carbon carbon bon formacion to our car venial. And we have this dangling Esther off of the end. So our new carbon carbon bond forms was from you know, it nuclear filic carbon attacking this electric filic carbon. It's also asked, why's this reaction? Example? The crossed Claes and reaction? Well, we're reacting. Want us there with on different Esther, not of itself

If we start with the following structure and react with and acid, we get this product, we have a one to metal shift that leads to this product here which undergoes an elimination reaction to give to final products to the major product. It is this here ch two ch three that is 23 dime Ethel Le Pen to being and then the minor product will be this here.


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