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For each of the 5 reactions (Synthesis of(2R,3R)-3-methyl-3-hydroxyp-ipecolic acid ,N-Boc-(2R,3R)-3-methyl-3-hydroxypipecolic acid,2R,3R)-EpoxygeraniolN-Benzylcarba...

Question

For each of the 5 reactions (Synthesis of(2R,3R)-3-methyl-3-hydroxyp-ipecolic acid ,N-Boc-(2R,3R)-3-methyl-3-hydroxypipecolic acid,2R,3R)-EpoxygeraniolN-Benzylcarbamate ,(2S,3R)-3-Methyl-3-hydroxypiperidine-2-methanol,andN-Boc-(2S,3R)-3-Methyl-3-hydroxypiperidine-2-methanol) :Draw the reaction, with the structure drawn in detail, andwithout abbreviations such as “TBDMS.”Draw the mechanism, using the specific compound. No “R”groups.Indicate the type of reaction, such as nucleophilic acyls

For each of the 5 reactions (Synthesis of (2R,3R)-3-methyl-3-hydroxyp-ipecolic acid , N-Boc-(2R,3R)-3-methyl-3-hydroxypipecolic acid, 2R,3R)-EpoxygeraniolN-Benzylcarbamate , (2S,3R)-3-Methyl-3-hydroxypiperidine-2-methanol, and N-Boc-(2S,3R)-3-Methyl-3-hydroxypiperidine-2-methanol ) : Draw the reaction, with the structure drawn in detail, and without abbreviations such as “TBDMS.” Draw the mechanism, using the specific compound. No “R” groups. Indicate the type of reaction, such as nucleophilic acyl substitution, and the parts of the reaction, identifying the leaving group, the nucleophile, etc. Provide the overall reaction sequence that involves your 5 reactions THANK YOU!!



Answers

Determine the mechanism of nucleophilic substitution of each reaction and draw the products, including stereochemistry.

Okay, so problems eight. You're asked to identify the leading group and nuclear violent each of these reactions and predict the products. So in impart a this is your substrate. It's rib Ramo contains, and you're after attack it with Oh, th th three. I wish all these out of them still in reform just because I think it's easier to see then condensed form s So this is going to attack in us and to fashion because this here, shown in blue, is the nuclear file. Nuclear files typically are the electron rich cheese. In a reaction, they usually have a negative charge, but they don't have to, but they will always have either a long pair or a pie bond. The leading group is what leaves the substrate. And in this case, Sharon Green, it's the Fermi. So for the products of this reaction, you would have something that looks like this because this a nuclear file substrate has replaced the bro me in the broom in his left. Okay, In part B, the reaction substrate is claro cycle vaccines, and it's attacked with the nuclear file sodium hydroxide, inorganic chemistry. You can leave off the counter ion which in this case is sodium. So I'm just going to write the CIA files, which in this case is hydroxide. And once again, this is the nuclear file because it has the low fares, and in this case, it has a negative charge. So it's a good nuclear about, and the leaving group in this case is going to be scoring. So it attacks in s into factions and the corn grew, please. And in its place as a product, this is formed Psychlo six in all, plus foreign clients. Okay. And c, the substrate a beautiful idea. And it attacked with Eva had ion, which is in three minus. I'm gonna show you specific of the reaction, and it's gonna kick out the eye because once again, a size is famously a vile and eyes the leading group. So if on s into reaction, it will form. No, what I did, I am so in solution or D. The substrate is bro mo like waxing and the nuclear file once again leaving out the counter Ion is cyanide. So sign is going to be the nuclear file because it has the negative charge one to get it doesn't have to have a negative charge, but it has a lone pair that can react and the living group is going to be growing. So this reacts menace into fashion, looking out for me informs, but from my client, and that's the fore problem, mate.

Waiting to draw the product that each of these nuclear Felix substitution react. The first step is going to be identify whether it's going to react by an S and two Rs and one. This is a strong nuclear file s. So it's going to favor us into reactions. And this is a second, uh, yeah, secondary alcohol light so I can react either s and one arrest into. But since the nuclear file a strong, it's going to be in Essen Turia. Our product is going to be there. And, B, you need to identify whether it's a strong nuclear file. Fist is a strong clear file because it bears the negative charge. And this is a primary alcohol allied, which means it can only react by s and two mechanism start product or B is gonna be the night instead of in alcohol or C. Our substrate is this. Yeah, and our nuclear file is water. So in this reaction, the nuclear file is weak. Meeting that it favors s into s and one reactions. Sorry. And the alcohol light is tertiary, meaning it can only react finding us in one. So our product for sea is going to be, uh, receiving mixture of products being this and this and we are substrate. Is this okay? In our nuclear file is ethanol. So once again, our nuclear file is weak. Which favors and Essen One reaction, and it's once again at a tertiary Alfa Hey, light, so it could only reacted by innocent one. So our product in this case is going to be another ischemic mixture. And it's going to be this for e our substrate business and our nuclear files. Is this so this is a strong nuclear file, meaning that it favours us into reactions in its That's a secondary awful. Hey, life. So I could be there s and one arrest into, but favors s into because technically, a file. So our product for this reaction going to be this for out our substrate is this and our nuclear file is this. Now, this is a weak nuclear file because it doesn't marinated charge. It's neutral, But this is a primary awful Hey, life so it can only be s into. So our reaction is going to proceed. Inform this product and it bears a positive charge. So you need to You can include the Orions as it's counter ayan

So still let the product. So the 1st 1 is tthe e Esther Formacion reaction, and it will generate 2345 Ito proper. Know it'll? Penton? Oi! Sorry. This is too see. Oh! Oh, See it to seek age. This reaction with heat, it basically will be high. Great. Um, so basically, this one will attack in this one. First, open this. See Obama. And then when the charge come back, it will cost the always group to leave. And basically it's ni hydration. And from ah, cycling on hide right six cyclic and hydrate. 12341234 or six six Memory.

So now we're gone. Problem twenty Problem eighty two from chapter twenty one here were given two reactions and were asked to determine the products for each car. Big Cilic acid reaction So first way are given Ah, this reaction his three ch too C o h. And we react with an h o h. So this here is an acid base reaction and the product here is simply the D protein ated acid coordinated with B Can I an sodium plus and we produce water. So that's for R A and part B. We are given another car Vic Selic acid. And this time we're reacting with an alcohol. So ch three ch too C h two o age and we further at H two s o for sulfuric acid. And what this does is this gives us the Esther This always group one of these old age groups Khun b. Protein ated this one here and it will leave as water and we get the Esther product when the two linked together So that ch three see age too ch too See plus H two o. Now this reaction here is a condensation reaction


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