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The following sequence, beginning with a cyclic hemiacetal (compound A); was part of a recently reported enantiospecific synthesis of powerful sex pheromone (curren...

Question

The following sequence, beginning with a cyclic hemiacetal (compound A); was part of a recently reported enantiospecific synthesis of powerful sex pheromone (currently used in pest management) of the mealybug Pseudococcus viburni (Tetrahedron Lett: 2010, 51 5291- 5293). Determine the structure of compounds Bj C and E formed in the reaction Be able t0 show the detailed mechanism for the whole process_HoCE:TshHealMeCulRO

The following sequence, beginning with a cyclic hemiacetal (compound A); was part of a recently reported enantiospecific synthesis of powerful sex pheromone (currently used in pest management) of the mealybug Pseudococcus viburni (Tetrahedron Lett: 2010, 51 5291- 5293). Determine the structure of compounds Bj C and E formed in the reaction Be able t0 show the detailed mechanism for the whole process_ Ho CE: Tsh Heal MeCul RO



Answers

An outline of a racemic synthesis of $\alpha$ -multistriatin, a pheromone of the elm bark beetle, is shown below. (Sections 21.3 and 21.4 ) (a) Suggest reagents for a one-step synthesis of 1 from but-2-yne- 1,4 -diol. (b) Give the IUPAC name of compound 1. (c) Suggest a reagent for a one-step synthesis of 3 from 2. (d) Suggest a structure of the product formed from the reaction of 3 with $\mathrm{HO}^{-} / \mathrm{H}_{2} \mathrm{O}$. (o) Name the functional group(s) present in compounds $2,3,$ and $\alpha$ -multistriatin.

23. Problem number 23 Fromthe Smith Organic chemistry textbook. Ah, and this problem asks us, um, to draw our Sorry. It asks us what cyclic product is formed from each di hale. I using the moronic Esther synthesis. Ah, and so we're giving these to Di Hale IEDs. Um, and remember the melodic Esther synthesis it's gonna be using, um, this moronic Esther and sodium ASAC side followed by, uh, agree. It's acid in heat. Um, and the thing to keep in mind is that the product of each of these is going to be a ring in this case, since it's a di hale I that we're starting from Ah, and it's gonna be a ring with one more carbon. Ah, then these starting molecule. So, for a we have three carbons with a chlorine on each end on DSO, our product is going to be a four member dring with a car box. Ilic acid. Okay, um and so B is gonna follow the same pattern. So we're starting from four carbons and an oxygen. So that's five Adams. And so our product is going to be a six member dring. Ah, and so that is going to look like this. So it's gonna be a six member ring with an oxygen in it. Ah, and then Pera to that oxygen is going to be a car box. Like acid. Okay, um, and that's the answer here. The explanation for this and the mechanism of how this occurs appears right above this problem in the textbook, if you need to review it, um, as I said, I think it's easiest to think. Think of this just in terms of just adding one carbon and making a ring of that many members. Okay, s So that's the answer to Chapter 23. Problem number 23.

Going on with the reactivity off Elkins and all kinds. So we have a few different examples to take a look at, so we'll jump straight into the first example that we have. So what we have is this starting material and then in the presence off P C I five, there are degrees south CIA. We found the following what we have ch three c c i to ch three. Let me have three equivalents of any NH two mineral oil and heat on what we form is an al kind. You have ch three C triple bond C H to have SP hybridized carbons associated with that triple bond. Next, what we have is ch three stage two c h be off to so again the same re agents of mineral oil Heat two equivalent of NH four plus we then generate our al kind against. We have C H three see triple bond C H without SP hybridized carbons while we're using all of those pill bottles. Now for our sad reaction, we have ch three c h v r c h two. We are using the same the agents that's have used all along to form or al kind, which is reminding ourselves or triple bond used with our SP hybridization. It's moving onto the final example. What we have is ch three c h double bond, C H two. Then we have the off to that gives us ch three c h p r ch to be off, have the addition off Burr mean We then have the same regents that we've used all along informing our al kind bond ch three c triple bond C H.

Hi, everyone. The ST Lucian ex center in the molecular is as follows. Hmm. Eugenic send in the molecular is as follows. So two days see the will or No, she Oh, okay, that is double bond. Little one ch two c another ch two ch teau the next he has to say yes to on then this. Now you know, stay. Does anything, Dad? And that Ma'lik it is this these things the state owes in Extender studio. Jenny, send out then next. Not this molecular heads Odd and named Shaima. I'm sorry. I'm a lot articulate so much and in China or articulate so much, they're not superimposing mirror images on each other. Then next, the other possibilities. Somewhere off this camp ponies, the or the possible. I saw much off this compound ease. Yeah, components. It's follows. Yeah. So mortal Gatorade's. Yeah. Okay. Okay. Look, season okay? Yes. Yeah. Wow. So this one day, they're about possibilities somewhere off this compound, right? Yeah. No, Uh, you know, this compound has s an in China. Okay? The components, I mean, compound shows is in Ngoma. Goodbye. What things

Hi everyone. The Dave off the reaction occuring in each step. Abe off reaction. Anchoring, anchoring, you know, in each step Spain is, as far loads follows. So first one, it's reduction of a kid can see here Step then a pro free action. So Step one, a deduction off on the king I killed Step two. The election off Kidan. We'll keep it on right then. Step three. Formation off. Messily automation off myself. Yeah, nestle it. That is good. Living roof. Good living growth and removed up or age. I mean more love or each group to form again. Then step four in words. Reduction up on the hill. Oh, of the king. And stay fighting once the monopoly Proton, that is deeper donation nation Then be overall killed off a product our pyro leading Toa do file off by a leading to do for you with respect toe initial records Sarees, respect toe initial. Thank you, Ricardo Sarid's is 20 sun wind. Certainly 1% The ST so this ill Can we explain as follows? That is, uh, Conde percent. Original Precursor is present in Draper ST. Okay, Original. Our initial brick garza is present. The name for Saint initial precursor is present 100%. So this gives Oh alc income parents 85% then these kids he don't compound 75 these girls kitten compound 75% 25% So 75% off 84 years, 63.75% Then this Kato again. What? Undergo a Riemann Off age group. Informational palkin. And they did 63.75%. So it's 63 point 73% off. 75% is 33.15% then Anakin Yeah, undergo reduction. The deduction. The released compound, you can say. And that girls 95% ill now 95% off. 63 points 25 years. 31 point sure 49 23%. Then these girls a wow for a new compound, buy a new compound. Who's allays 18%. It did percent off 31.49 to 5%. Nothing but 27.71 passing


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