What products would you expect from oxidation of the following alcohols?
a. CH₃CH₂CH₂OH
b.
c.

Question

What products would you expect from oxidation of the following alcohols?

a. CH₃CH₂CH₂OH

b.

c.

Accepted Answer

Hi, everyone. Here's our next question. It says, predict the product that will form from the complete oxidation of the alcohol shown below. And we have three different alcohols to look at. So we need to think about what is the result of an oxidation of an alcohol? Well, let's recall that that depends on what type of alcohol it is if it's a primary alcohol, so that the carbon that is attached to the hydroxy group has only one R group, then the alcohol is completely oxidized in two steps first to an aldehyde and then to a carboxylic acid. So since our question is asking us for a complete oxidation, we know that our product will be a carboxylic acid. If we have a secondary alcohol where that carbon bonded to the alcohol group has two R groups, it gets oxidized to a ketone and can't react any further. And if it's a tertiary carbon, our tertiary alcohol, excuse me, where that carbon has three R groups, then there is no reaction, it cannot be oxidized. So let's look at our three alcohols and determine for each of them what the product will be. Well, and number one we have a cy butane ring and then it has a three carbon chain, the carbon that's attached to the cyclo butane ring also has a hydroxy group. So we want to focus on the carbon that is attached to our oxygen in the alcohol group. And we see that that carbon is bonded to two other carbons. It has two R groups, one on either side. So we have here a secondary carbon. So we know that it will become our secondary alcohol, excuse me. So we know that it will become a ketone. So the co single bond of the alcohol becomes the carbonel group in our ketone. So if we draw that product, we have our cyclo butane ring, it has a single bond to the carbon that was attached to the hydroxy group. That carbon now has a double bond to an oxygen and it's lost its hydrogen. So it's now a single c double bonded to an O and then with an ethyl group attached CH two CH three. And to describe this properly, if we want to have the knee, this would be one Cyclo butyl, one prop with the carbonel group on carbon one as well as the cy butane. So that's our product for molecule number one. Now let's move on to number two. Number two is written as a condensed structure CH three CH and then in parentheses, CH three CH two C H2O H. So we see that alcohol group at the very end of the molecule. So there's its carbon that it's attached to, which is the terminal carbon in the chain. And so that terminal carbon is only attached to one other carbon. So this is a primary alcohol. So we know it will go all the way to a carboxylic acid. So I'm going to draw this a little farther down, I'm running out of space. So for molecule number two, let's write out our structure and we'll write it in the condensed form since that's how it was given to us. And it's simple enough since we're dealing with the terminal carbon in this molecule. So we have CH three ch and then in parentheses, ch three CH two. And now we're on that last carbon which is bonded to the oxygen. And again, our alcohol has now become a carboxylic acid. So we would write this as C we know this c now has a double bond to an O and also a bond to, oh, so this is a carboxylic acid with one methyl branch. So it will be three methyl and we have four carbons in the main chain. So Banic acid. So once again, we had a primary alcohol here. So that is now completely oxidized two a carboxylic acid. And finally, we go to our last molecule here and it shows us that we have a three carbon chain with the oxygen group on the middle carbon C three C with an oh group CH three. So once again, if we look to the carbon that's bo bonded to our oxygen and the alcohol group, it has two carbons attached to it, two R groups. So we know this is another secondary alcohol. So were looking for another kone. So we would have CH three. There's our first carbon, the middle carbon C now with a double bond to the O and then another CH three. So what we have here is two propan since we have a three carbon chain there. And again, being a secondary alcohol, we have a kone product. So here's all three of our products. Again, we had secondary alcohol in the beginning oxidized to a ketone. Our number two molecule was a primary alcohol that got oxidized to a carboxylic acid. And our number three molecule is secondary alcohol that got oxidized to a ketone. See you in the next video.

What products would you expect from oxidation of the following alcohols?
a. CH₃CH₂CH₂OH
b. <IMAGE>
c. <IMAGE>

Verified Solution

Key Concepts

Oxidation of Alcohols

Types of Alcohols

Oxidizing Agents