Draw the structure and name the product formed if the...

Draw the structure and name the product formed if the following alcohols are oxidized. Assume that an excess of the oxidizing agent is used. If the alcohol is not expected to react with a chemical oxidizing agent, write NR (no reaction). (a) $\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{CH}_{2} \mathrm{CH}_{2} \mathrm{OH}$ (b) 2-butanol (c) 2-methyl-2-propanol (d) 2 -methyl-1-propanol

Draw the structure and name the product formed if the following alcohols are oxidized. Assume that an excess of the oxidizing agent is used. If the alcohol is not expected to react with a chemical oxidizing agent, write NR (no reaction).
(a) $\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{CH}_{2} \mathrm{CH}_{2} \mathrm{OH}$
(b) 2-butanol
(c) 2-methyl-2-propanol
(d) 2 -methyl-1-propanol

Key Concepts

Oxidation of Alcohols

This concept involves the transformation of alcohols into carbonyl compounds (or further into carboxylic acids) through the loss of electrons facilitated by an oxidizing agent. The nature and extent of oxidation depend on the type of alcohol (primary, secondary, or tertiary) as well as the conditions used, such as an excess oxidizing agent.

Primary Alcohols

Primary alcohols have the hydroxyl group attached to a carbon atom that is connected to only one other carbon. Under strong oxidation conditions or with an excess oxidizing agent, primary alcohols commonly undergo oxidation beyond the aldehyde stage to form carboxylic acids.

Secondary Alcohols

Secondary alcohols feature the hydroxyl group bonded to a carbon atom that is attached to two other carbons. Their oxidation typically results in the formation of ketones, as the process stops with the generation of the carbonyl group and usually does not proceed further under standard oxidizing conditions.

Tertiary Alcohols

Tertiary alcohols have the hydroxyl group attached to a carbon that is bonded to three other carbons. They resist oxidation by most oxidizing agents due to the absence of a hydrogen atom on the carbon bearing the hydroxyl group, making it difficult to remove electrons for further oxidation, and as such, they usually show no reaction under typical conditions.

Transcript

00:01 So before we start this question, i'm just going to review the oxidation of various alcohols.

00:06 So when you go ahead and oxidize a primary alcohol, which again, remember, is just your alcohol group attached to your carbon.

00:17 And then that carbon is only attached to one other carbon.

00:22 So just in our group.

00:23 So when you go ahead and oxidize a primary alcohol, this compound is going to go straight to a carboxylic acid.

00:31 And remember that carboxylic acid is just that c double bonded o oh, with that r group.

00:40 Now, when we go through a complete oxidation of a secondary alcohol, which remember is when that carbon is connected to two other carbons.

00:55 So when we do a complete oxidation of something that looks like this, we end up with a ketone, which is just that double bonded o and your two.

01:06 To r groups.

01:09 Now a tertiary alcohol, which remember is, sorry, that tertiary alcohol, which is that c, and it's connected to three other r groups.

01:29 When we go ahead and try to oxidize a tertiary carbon, we get no reaction, which we can signify just by writing nr.

01:37 So now that those definitions are out of the way, let's look at our first compound.

01:42 We are going to oxidize.

01:46 So when we look at this, we can see that this oxygen right here is connected to this carbon right here, and that carbon is connected to only one other carbon, which makes this alcohol a primary alcohol.

02:01 So if we were to go ahead and fully oxidize this alcohol, we would get something like a carboxylic acid, which remember is just that c double bonded o, oh.

02:20 So that's what that structure would look like completely oxidized.

02:23 And now all we have to do is name it.

02:24 And remember that carboxylic acids have the suffix annoic acid.

02:28 And this is a four carbon compound.

02:30 So we can just title this butenoic acid.

02:38 All right, part b.

02:40 Now, if we were to fully oxidize two butanol...

Please give Ace some feedback