0:00:00.000,0:00:00.390


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What I want to do in this video[br]is talk about a bunch of

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molecules or classes of[br]molecules that can be derived

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from carboxylic acid.

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And just to show a specific[br]example I'll show things that

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can be derived from[br]acetic acid.

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And just as a review, acetic[br]acid looks like this.

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The common name, as I just said,[br]is acetic acid, and if

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you want to use the systematic[br]name, you look for the longest

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chain, which is right[br]over there.

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There's two carbons.

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So we use the eth- prefix, so[br]it's ethan-, and since this is

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a carboxylic acid, it[br]is ethanoic acid.

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Now, the derivatives of acetic[br]acid, and we can later

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generalize this to all[br]carboxylic acids.

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We really just have to change[br]what's going on in this carbon

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chain right here.

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It won't have to necessarily[br]just be two carbons.

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It can just keep going.

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It could have benzene rings,[br]whatever, and that would

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change the name.

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But really, I just want to give[br]you the gist and the gist

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of the naming.

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So if we were to replace this[br]hydroxyl group with an amine,

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and in future videos we'll see[br]how that is done, so let me

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just draw the acyl group.

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So the acyl group is just[br]that right over there.

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And we're just going to keep[br]changing what's bonded to the

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acyl group right over here.

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So if this is bonded to an[br]amine, so let me draw-- well,

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this would be the simplest amine[br]right over here, which

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would be NH2.

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This thing right here it's[br]called an amide, and if we

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were to give this its common[br]name, it would be acetamide.

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This particular example[br]would be acetamide.

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And if we wanted the systematic[br]name for it, it

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would be ethanamide.

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You have two carbons right there[br]so it is ethanamide.

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Now the natural question is,[br]all amines won't just be

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primary, you might have other[br]things other than hydrogens

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attached to it, other radical[br]groups, other carbon chains,

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so how do you name those?

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And so if you had a molecule[br]that looked like this, and

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actually, let me just change[br]things up a little bit so that

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we diverge a little bit[br]from the ethane route.

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So let's say you had three[br]carbons bonded or part of the

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acyl group right there.

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And then, we are bonded to a[br]nitrogen, which is bonded to a

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methyl group and then[br]another hydrogen.

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In this case, you start naming[br]with this methyl group right

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here and to show that that[br]methyl group is attached to

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the nitrogen, you call[br]this N-methyl.

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And then you look at the chain[br]that forms the acyl group, the

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carbon chain.

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We have one, two, three carbons[br]so it is propanamide.

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If you had another methyl here[br]you would say N comma

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N-dimethyl.

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If you had a methyl here and[br]a propyl group here, you

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would've called it[br]N-methyl-N-propyl-propanamide.

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So hopefully that gives[br]you a sense of amides.

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Now, and this is something we've[br]seen before so it's a

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little bit of review, if you[br]have something that looks like

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this, I'll have it attached[br]to a methyl

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group right over here.

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We've seen this before.

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This is an ester.

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And if we have an-- let me[br]actually make the part that

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makes it an ester in blue[br]to diferentiate it.

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We keep substituting what is[br]attached to the acyl group.

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Let me label it.

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This right here is called[br]an acyl group.

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That right there is[br]an acyl group.

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So right over here, for the[br]ester, if we were to give it

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its common name, and we've[br]seen this ester

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before, it is acetate.

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And if we wanted to give it its[br]systematic , name you look

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at the longest chain, one, two[br]carbons so it is ethan-- and

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you don't call it ethanoic[br]acid anymore.

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You call it ethanoate,[br]just like that.

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Now, the next one, and we[br]haven't seen this one before,

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and it looks complex, but when[br]you really break it down into

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its constituents,[br]it's not so bad.

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So let's say we have a molecule[br]that looks like this.

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So we have one acyl group bonded[br]to an oxygen, which is

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bonded to another acyl group.

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So it's almost like you have two[br]carboxylic acids that have

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been joined together.

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And you really do have two[br]acyl groups joined by an

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oxygen here.

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This is called an anhydride.

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And they look very complex, but[br]you just have to realize

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they're two carboxylic acids[br]attached to each other and

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usually the same one.

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Most anhydrides you're going[br]to see in organic chemistry

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are formed from the same[br]carboxylic acid, so how ever

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many carbons you have on this[br]end, you're normally going to

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have on this end.

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So the way the name these is you[br]name it just the same way

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that you would have named the[br]carboxylic acid, but instead

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of writing the word acid, you[br]write the word anhydride.

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So this right here would[br]be acetic anhydride.

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It's derived from acetic acid.

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This right here is[br]acetic anhydride.

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Or the systematic name is, we[br]have one, two carbons so it's

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ethanoic anhydride.

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And just to make things clear,[br]if this molecule instead of

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that, if we had something that[br]looked like this, where the

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carbons chains on either[br]end had three carbons.

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One, two, three, one,[br]two, three.

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We would call this propanoic[br]anhydride.

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In the unusual circumstance, and[br]it is unusual, where you

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would see different carbon[br]chains here, you would list

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each of them.

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So if this had two here and[br]three here, it would be

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ethanoic propanoic anhydride.

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But that is very,[br]very unusual.

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Normally, these carbon chains[br]on either end of-- or both

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acyl will groups will contain[br]the same number of carbons.

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Now, the last carboxylic acid[br]derivative that you should

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know about, and we've already[br]seen it, are the acyl halides,

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and, in particular, the[br]acyl chlorides.

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So let me draw it[br]right over here.

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So you have your acyl group[br]right there and then it is

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bonded to a chlorine and this[br]right here is an acyl

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chloride, maybe the most[br]intuitive name.

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This right here is an acyl[br]group and then you have a

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chlorine, so it's an[br]acyl chloride.

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And we've seen this exact[br]acyl chloride.

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It's derived from acetic acid,[br]so this is acetyl chloride.

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But if you wanted to give it[br]its systematic name, and we

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haven't seen it's systematic[br]name before, we have one, two

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carbons so it is ethanoyl.

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This tells us that we are[br]dealing with an acyl group.

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Ethanoyl chloride is how[br]we would name this.

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And if this had three[br]carbons, it would

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be propanoyl chloride.

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So, hopefully, that gives you[br]at least a good introduction

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to the differences in structures[br]of all these groups

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and an introduction[br]to naming them.

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In the next video, we'll talk[br]a little bit about the

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relative stabilities and then[br]it'll give you good intuition

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on which direction a[br]reaction might go.

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Are you more likely to go from[br]amide to an acyl chloride or

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from an acyl chloride to an[br]amide or anything in between?

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