Which of the following alcohols can undergo oxidation? Draw the line structure of the product expected for those that can. Assume an excess of oxidizing agent is present.
a.
b.
c.

Question

Which of the following alcohols can undergo oxidation? Draw the line structure of the product expected for those that can. Assume an excess of oxidizing agent is present.

a.

b.

c.

Accepted Answer

Hi, everyone. Welcome back. Our next problem says, identify the substance that can react with an oxidizing agent, provide the line structure of the expected product that will form for those that can assume complete oxidation. And we have the structures of three different alcohols. So we need to think about how different types of alcohols will react with oxidizing agents. And that depends on the structure of those alcohols and particularly how many R groups are on the carbon that is bound to the hydroxy group. So we know that if we have a primary alcohol, just one R group on our carbon, it can be completely oxidized in two steps first to an aldehyde. And then since our problem has assumed complete oxidation, it can become a carboxylic acid. If we have a secondary alcohol with two R groups on that carbon, it gets completely oxidized to a ketone and then stops there. And if we have a tertiary alcohol with the three R groups, there is no reaction with an oxidizing agent because that oxidation reaction has to remove a hydrogen from the carbon. And in the case of a tertiary alcohol, there is no hydrogen on the carbon. So let's begin looking at our different structures. In number one, we have a cop pentane ring and on one of its carbons, it has two bonds, it has an ethyl branch and then it has the hydroxy group that makes it in alcohol. So this is a tertiary carbon, the carbon that our hydroxy group is attached to has four bonds and no hydrogens. It's our groups, R one and R two are other carbons in the ring. And R three is that ethyl group. So there's no reaction in this case, as that carbon has no hydrogens available for an oxidation reaction. So that's our answer for. Number one, no reaction possible. Now, let's look at number two, the number two, we have a cyclops ring with an ethyl branch and a hydroxy group, but they are on adjacent carbons. So when we look at the carbon that our hydroxy group is attached to, it is a secondary alcohol. It has two R groups which are the two adjacent carbons in the ring. So in this case, we know, so we draw our cyclen ring with its apple branch and then instead of the alcohol group, that carbon is now have a double bond to an oxygen in a, in a carbon group. So that is our ketone. We have two ethyl proin as our product here. So let's move on to our third structure which is another cyclops and on one of its carbons, it has a methyl group and then another carbon bonded to an a hydroxy group to make it an alcohol. So note that the carbon of our alcohol is not on the ring but is one carbon away from the ring. So this is a primary alcohol since our carbon just has the one R group, which is the cycling ring itself. So in that case, our primary alcohol is going to go all the way to a carboxylic acid. So we're going to draw our Cyclin ring, fix that a little bit, the methyl group and then the bond to the carbon. But that carbon now has a double bond to an oxygen and a single bond to an O group tidied up that structure a little bit. So that product we have is one methyl cyclops, carboxylic acid. So again, since it was a primary alcohol to be completely oxidized, it goes all the way to carboxylic acid from alcohol. So there we have our two products from the two that react. And of course, instruction number one being a tertiary alcohol, there's no reaction. See you in the next video.

Which of the following alcohols can undergo oxidation? Draw the line structure of the product expected for those that can. Assume an excess of oxidizing agent is present.
a.
b.
c.

Verified video answer for a similar problem:

Key Concepts

Oxidation of Alcohols

Types of Alcohols

Oxidizing Agents

Which of the following alcohols can undergo oxidation? Draw the line structure of the product expected for those that can. Assume an excess of oxidizing agent is present.a. b. c.

Verified video answer for a similar problem:

Key Concepts

Oxidation of Alcohols

Types of Alcohols

Oxidizing Agents

Which of the following alcohols can undergo oxidation? Draw the line structure of the product expected for those that can. Assume an excess of oxidizing agent is present.
a.
b.
c.