Show how you would accomplish the following syntheses.
(c) hexan-...

Question

Show how you would accomplish the following syntheses.
(c) hexan-1-ol → 2-hydroxyheptanoic acid

Accepted Answer

All right. Hi everyone. So for this question you must propose the re agents required for the following conversion and the conversion in question is from Butin one all to two hydroxy Penton OIC acid. So let's draw it out first. So Butin one all our starting material is going to be a four carbon chain Right? With an O. H. group attached to carbon one. So we're going from butin 1022 hydroxy Penton OIC acid. So instead of a four carbon chain we have a five carbon chain. So we have five carbons like that. And on the first position we have a carb oxalic acid group. This is our carb oxalic acid And we have an O. H. on position two. So before we start talking about the steps that we can take to get to this point. Right? What I want to bring to your attention is that two hydroxy Penton OIC acid is what we refer to as an alpha hydroxy acid. And recall that if our carbonnel here of our acid is the reference point, then the alpha position is going to be one carbon over from the reference point. So because we have an O. H group on the alpha position, it is an alpha hydroxy acid. So now um recall it a convenient way to synthesize an alpha hydroxy acid is from a cyan oh, hydrate hydrant mhm and SIA no hydrants recall that they look something like this. So we have a night trial and we have an O. H group bound to the same carbon. So this is our sion a hydrant and our cyan a hydrant can be converted to an alpha hydroxy acid relatively easily. So let's go through what that would look like. Right? Our first step given that we have a primary alcohol is the oxidation of it. So recall that if we were to react a primary alcohol in this case our Beauty in 10 with an oxidizing agent like PCC, we're going to generate an alga hide. So we're gonna have the same four carbon chain but we're gonna have an al to hide here instead of a primary alcohol. So from this album hide we can get to our cyan a hydrant. Right? Because our sign a hydrant if we add in cyanide to the system in the presence of H. C. N. Then what's going to happen is that our cyanide is going to attack the carbon carbon and it's going to generate a cyan a hydrant after the oxygen is protein ated. So we're gonna have four carbons here, we're going to have an additional carbon because of our night trial group. And like I said before we're going to have, ohh so this is our cyan a hydrant and this is working out pretty well right? Because notice how from Beauty in one all to two hydroxy pentatonic acid, we added a carbon and the presence of this night trial group did precisely that right now we have um Now we have five carbons in our intermediate product. So as our last step, right, recall that Saya no hydrants can undergo hydraulic sis um in acidic conditions relatively easily. So um the night trial is what's going to be hydrolyzed, right? So if we have H30 plus in the presence of heat, then that night trial is going to get hydrolyzed to our alpha hydroxy acid. And that is going to be the answer to this question. So on the bottom here, I'm gonna do a quick recap right. Our first step was the oxidation of a primary alcohol with PCC. And the second step was um the addition of cyanide in the presence of H. C. N. To generate our Saya No hydrant. And then our last step was the hydraulic basis of the night trial in our sion, a hydrant via acid and heat. So that is going to be our synthetic sequence for this question. And thank you very much for watching. I hope you found this helpful

Show how you would accomplish the following syntheses. (c) hexan-1-ol → 2-hydroxyheptanoic acid

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