What alcohols would you oxidize to obtain the following carbon...

Question

What alcohols would you oxidize to obtain the following carbonyl compounds?

a.

b.

c.

Accepted Answer

Hi, everyone. Welcome back. Here's our next problem. Provide the alcohol that can be oxidized to yield the carbon containing compounds shown below. We have three different compounds provided with carbonel groups in them. So let's look at molecule number one. And we see that here we have a ketone because the carbon in the co double bond has two R groups. So I'm going to label them R one and R two, they're symmetrical. They both have 123 carbons with a methyl group on carbon two. And then we have the central carbon bonded to and oxygen. So we know that ketones can be the result of oxidizing a secondary alcohol. So our carbon oxygen double bond each of those atoms. I'm going to go ahead and highlight that would have had a hydrogen removed from it in that oxidation process. So to redraw my alcohol, I'll just need to put hydrogen back on each of those. So let's first draw my R one group. Of course, R one and R two are the same. But we know we have three carbons here ch three chch two and then that middle carbon has a methyl branch coming off of it. Ch three. Now I've reached my carbon that's in the carbonel group. So I draw that carbon I need to add back on a hydrogen, which I'll write in red. So we can kind of see that that's the one that went back in. So it's now ch and then I draw the link to my oxygen, which is now an alcohol. So it's a single bond to O with an H added on to the oxygen. So right in the middle, I have the ch bonded to an oh and then just add in my R two group. So I have my three carbons ch two chch three and a methyl group onto that middle carbon. So there we have it, the alcohol that this came from a secondary alcohol and we've made it into CH three ch with ach three branch ch two ch with an oh group ch two ch with ach three branch CH three as its structure. Now let's move on to molecule number two, this is a cyclohexane ring with a carbon bond on one side that we call carbon one and a methyl group on the other side, pera to it on carbon four. So we have another ketone here. In this case, the R groups are the two other carbons in the ring adjacent to it in the ring. So to get the alcohol, we'll draw our cyclohexane ring because that will remain the same the methyl group on carbon four remains the same. We just have to change the ketone into a secondary alcohol. So instead of a double bond to an oxygen at carbon one, it will be a single bond to an oh group, the other hydrogen would have been added to this carbon one. But in a line structure like this, the hydrogens are understood and not drawn explicitly. So that one was pretty straightforward. We have our cyclohexane with an oxygen on carbon one and a methyl on carbon six or carbon four. Excuse me. Now, let's move on to molecule. Number three, we have a benzene ring connected to 123 carbon molecules. Carbon Adams, excuse me with a methyl branch on the middle one. And then we have one last 1/4 carbon at the end, which is part of a carboxylic acid group. So these are carboxylic acid. We have an R group which is that carbon chain with a benzene ring at the end of it. And then we have a double bond to an O and a bond to an oh. So let's recall that carboxylic acids can be the product of this double oxidation of a primary alcohol. So the primary alcohol gets oxidized to an aldehyde group, which in the presence of more oxygen can be oxidized to a carboxylic acid. So we're going to look for the primary alcohol that started it all. So we recall that the aldehyde would have our, our group. I'm just gonna put a squiggle because I'll redraw it for the alcohol structure. And then we would have our carbon which still has ac O double bond, it's an aldehyde. But instead of the bond to the oh group, that's now just a hydrogen on that carbon. So now we have our aldehyde. Let's go back and draw the primary alcohol it came from. So we'll draw our group. So we have or benzene ring and then we have that chain of 123 carbons. So benzene ring attached to CH two chch two and the middle one there which is ch has ach three group on it. And now we get to our fourth carbon which was an aldehyde. So we need to put another hydrogen onto this carbon and then a hydrogen back onto the oxygen when we break the double bond. So it will now be CH two instead of ch and then it will finish up with. Oh, so we have our final molecule here, our benzene ring and then 1234 carbons finishing up in an oh with a methyl branch on that second carbon from the benzene ring. See you in the next video.

What alcohols would you oxidize to obtain the following carbonyl compounds?
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b. <IMAGE>
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Key Concepts

Oxidation of Alcohols

Types of Carbonyl Compounds

Reactivity of Alcohols

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