Predict the products of the reactions of the following compoun...

Question

Predict the products of the reactions of the following compounds with:

1. chromic acid or excess sodium hypochlorite with acetic acid.

2. PCC or NaOCl (1 equivalent) with TEMPO.

a. cyclohexanol

b. 1-methylcyclohexanol

c. cyclopentylmethanol

Accepted Answer

All right. Hi everyone. So for this question it asks what are the expected products when each of the following compounds react separately with PCC and chronic acid. So PCC and chronic acids are two oxidizing agents. And so now before we do anything let's compare them really quickly. So over here I'm gonna write PCC. And over here I'm gonna write our chronic acid. I'm just gonna write the formula instead. So for P. C. C. And chronic acid just gonna make a little table. So recall that PCC is going to be a weaker oxidizing agent than our chronic acid. So when you react a primary alcohol and you oxidize it with PCC you're going to generate an alga hide. Just make sure I'm spelling this correctly. Right. So like I said before, if you react a primary alcohol um with PCC you generate an al to hide because it's a weaker oxidizing agent than chronic acid. And with that being said recall also that if you react a secondary alcohol this time with PCC you're going to generate a keto. So that's P. C. C. And so now let's talk about chronic acid. So chronic acid is actually a very strong oxidizing agent and it is not easy to work with. So if P. C. C. Is going to generate an al to hide if you reacted with a primary alcohol, chronic acid is going to convert a primary alcohol all the way to a car box silic acid. So that's car box silic acid because it's so much stronger it's that much stronger of an oxidizing agent than PCC is. So a primary alcohol is going to become a carb oxalic acid and a secondary alcohol is going to also become a keto. So that's pretty much it. And now let's get started by drawing out our starting material are first starting material because we have cyclo hep channel one methyl cyclo hep panel and cyclo hexane, methanol. So let's get started with our cyclo hep panel. I'm gonna write I was gonna say cycle hex and all but that's not right. So for part a we have a seven carbon ring that looks wonky but that's seven carbons. And we have an O. H. Troop up top here. So if we react our cyclo hep panel with PCC just to start us off. If we look at our little flow chart here um cyclo hep total is a secondary alcohol. So we know that this is going to generate a ketone if we reacted with Pcc. Yeah so this is our same seven carbon ring but now we have a car bottle instead. Yeah so that's our P. C. C. Product. And if we react it if we react are cyclo hep panel with chronic acid according to our flow chart. The product is actually going to be the exact same. It's still going to be oxidized to a ketone. So this is our seven carbon chain seven covered ring I should say. And here's our card bottle and now we ended up with a ketone after reacting with both chronic acid and pcc. If you were if you were to react either one of them you get the same product. So with that being said let's proceed to part B. And part B. Okay I don't need to scroll up. So for part B. Which I'm going to write down here off to the side. We have one method cyclo hep panel. So we have the same seven carbon ring. Right? Just trying my best here too. We have a methyl group and we have our O. H. group both on position one. So just as a quick interlude, right recall for a second that tertiary alcohols are actually very resistant to oxidation. They're not going to be oxidized even if you have something strong like chronic acid. So the reality is is that our one methyl cyclo hep panel is not going to react. So there will be no reaction with either re agent with either oxidizing agent because like I said before it's a tertiary alcohol. So it's going to be very very resistant to that sort of reaction. So with that being said let's proceed on to part C. And now I can scroll down and part C. Which I'm gonna write out in red, Part C. Is going to be cyclo hexane, methanol. So cyclo Hexcel methanol It's going to be a six member ring this time with methanol attached to it. So we have one carbon and an O. H. Over here. So let's start by first reacting our cyclo hexane methanol to PCC. And if we look at our flow chart here our table, I guess you could say for a second if we react with PCC because it's the weaker oxidizing agent we're going to generate and all the hide. So let's draw what that would look like. If we react this molecule with PCC we're going to end up with a six member ring all the same. But we're going to have an alder hide instead of a primary alcohol. Like. So now if we react are cyclo hexane, methanol with chronic acid because it's a primary alcohol, we're actually going to end up with a carb oxalic acid. It's going to be oxidized all the way to a carb oxalic acid. So if we react this with chronic acid we're going to get the same six member ring. Except now, instead of that primary alcohol, we have a carb oxalic acid. So that is pretty much it for all of our parts. Right? So I'm just gonna highlight our re agents and our products based on the starting materials that we have. So part B. Didn't react at all. No matter what re agent you put in because it's tertiary and then for A. And B. Well for a we got ketones for both. Right because they generate the same product for secondary alcohols. And for C we got an al to hide or a carb oxalic acid. So thanks for watching, and I hope you found this helpful.

Predict the products of the reactions of the following compounds with:
1. chromic acid or excess sodium hypochlorite with acetic acid.
2. PCC or NaOCl (1 equivalent) with TEMPO.
a. cyclohexanol
b. 1-methylcyclohexanol
c. cyclopentylmethanol

Key Concepts

Oxidation Reactions

Reactivity of Alcohols

Selectivity of Oxidizing Agents

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