Okay gang, we're going to be covering chapter three today in the Smith Organic Chemistry textbook, which deals with the second topic I call Unit 2, which is about functional groups. It is chapter three in the Smith text, although I prefer to discuss it before chapter two. Okay, so...
It turns out that there are an enormous number of organic molecules that exist in the universe. It's like on the order of 10 to the 200 or 10 to the 300 or something like that. It's just phenomenal. If you kind of downsize that a little bit, and I read an article recently where some theoreticians developed an algorithm and used a computer to, the algorithm on the computer, to predict the total number of compounds that would be of what we call a druggable size, a size of a molecule that can be used as a drug that contains carbon, hydrogen, oxygen, nitrogen, sulfur, you know, the common elements that we see in living systems.
That algorithm spit out the number of 10 to the, between 10 to the 23 and 10 to the 30, okay, different drugable or drug-sized organic molecules. So that's an enormous number of compounds. So how do you keep it all straight?
I mean, we can't even cover a couple thousand in a class like this. Okay. Well, luckily for us, it turns out that those 10 to the 23 or 10 to the 30 or the 10 to the 300 that exist in chemical space that are possible to make or possible to exist, we can take those and we can sort them. And we can put them in boxes, so to speak.
Kind of like when early biologists began to look at the world around us and start saying, you know, there's all these living systems, but they're not all identical. And so we're going to take, we're going to say, you know, the fish are different than the horses, and the horses are different than the cows, and the cows are different than the giraffes. And, you know, and they began to come up with the idea of a genus and the idea of species.
and families and so forth. Basically, humanity's been sorting things from this very complex world we live in for ages. For many, many hundreds of years, humanity has had a tendency to sort and take things that are scattered all over the place and try to organize them.
Well, luckily for us, those 10 to the 23 to 10 to the 30 organic druggable molecules are even more molecules if you don't consider those are just druggable, you can sort them into different categories according to their function. Okay. And so that brings us to this idea of functional groups. Okay.
And so there's a limited number of functional groups and you can sort any organic compound that we'll be talking about this semester into one of these possible functional groups. And I lost my pointer. That has always been true when it's an arrow.
So, or, you know, yeah, an arrow. So I'm going to go back to the laser pointer, and here we go. And so this unit and this chapter in the Smith book, chapter three, is about functional groups.
Groups on the molecule that give rise to its function, how it behaves in terms of its reactivity. what its physical properties are, and so forth. Okay, and there are luckily a limited number of functional groups. It all depends on what source you look at. Different textbooks say there's a different number, and different ones kind of don't subdivide some functional groups and so forth and so on, but here are some general ones.
All right, I got this scheme off of Wikipedia because it's not patented or not patented. It's not copyrighted, so this is copyright free. And so they call us chemical class, but it really ought to be called functional group. So if you're taking notes, this really should be the functional group column. And I'm going to show you that the charts in our textbook also don't use the right classification.
I don't know what's with these authors, but that chart is on the inside flyleaf of your hard copy textbook, the Smith textbook. She's got the functional group column mislabeled. At any rate, this is the functional group, and the first one we want to talk about are the alkanes. The alkanes are the entry-level, kind of most boring organic compounds of all. They contain only carbon and hydrogen.
with single bonds, no double bonds, no triple bonds, no oxygen, no sulfur, no nitrogen, no nothing, just carbon, hydrogen. They call that a hydrocarbon. Hydrocarbon. That word is down here along the side, hydrocarbon. Don't worry about this word here for a minute, but hydrocarbon is an organic molecule that just has hydrogen and carbon.
And an alkane is a hydrocarbon. You name them by tacking on the A-N-E. e suffix we learned the names of the first 10 ones uh 10 alkanes in um in chapter one uh here's an example ethane but the 10 you remember them they're methane ethane right propane butane pentane hexane heptane octane nonane decane yeah that's the first 10 all righty uh another kind of hydrocarbon that contains just carbon and hydrogen are the alkenes Alkenes are characterized by having at least one carbon-carbon double bond. I'm not talking about a triple bond. I'm saying at least one.
You could have two alkenes. I call it a diene, but we're splitting hairs here. We won't quite get to it. This will build on complexity.
So for right now, we're just looking for the presence of at least one carbon-carbon double bond, and that's an example of an alkene. The suffix there, you add E-N-E. So the three carbon alkene is propene.
The four carbon alkene is butene. Five carbon alkene is pentene, et cetera, et cetera. Here's the two carbon alkene ethene or ethylene.
Ethylene is a common name. That's the IUPAC name. IUPAC stands for International Union of Pure and Applied Chemistry. And there's a set of rules that we'll be learning as we go along. And, um...
This is kind of a common name that people kind of adopted and IUPAC accepts, but this is the IUPAC name. And we'll learn how to name all of these in more detail as we go along. Okay. Another kind of hydrocarbon is an alkyne.
And alkynes share in common that they have a carbon-carbon triple bond. And at least one. You could have another one down the chain.
You can have di-ynes or tri-ynes or what have you. But what you're looking for is a carbon-carbon triple bond. You name these by adding the suffix Y-N-E onto an alkane name. So the four-carbon alkynes name is butyne, the five-carbon pentyne, six-carbon hexyne, etc. We won't worry about the nomenclature for now, but just be aware that this is coming.
Another kind of hydrocarbon is called an aromatic hydrocarbon. And these have also been referred to as benzene derivatives. And so the functional group would be the benzene ring, and the benzene ring looks like this.
Okay, from this chart, don't worry about this group name. We'll learn about these later. So don't, you know, scribble that out.
Don't worry about that. This is the functional group class, alkane, alkene, alkyne, aromatic hydrocarbon. I prefer you use aromatic hydrocarbon, although this chart used benzene derivative.
Okay, and basically, aromatic hydrocarbons share in common this six-membered ring with alternating double bonds. Now, we'll learn in 352 that having three alternating double bonds in a six-membered ring makes this molecule very different than an alkene like this that is not in a ring, and when there's not three of them. So this actually has very, very different properties, hence it warrants its own functional group name, and that is aromatic hydrocarbon.
Okay. Here's an example, cumin. And yeah, so we've gone through four already.
Okay. Alrighty. Now in your textbook, both in a table in the chapter and in the, you know, fly leaves inside the front cover, she has tables and she calls that the functional group.
That's wrong. Okay. That is not right. Okay.
The hydroxy group is not a functional group. The alkoxy group is not a functional group. I don't know why she used that. Where she says type of compound, the vast majority of textbooks out there and what I learned and I think what every MCAT and DAT and GRE is going to be asking you is in this column. These are your functional groups.
Take and fix your textbook. Make note of that. That she should have re... Labeled this calm. I should email her about that.
I never have I've emailed her about something else that she had an error And she's not perfect. I think I've already made the joke that even Moroni drops his trumpet every once in a while So, you know, I'm not perfect either. I thought I was wrong once, but I was mistaken.
You probably heard that little joke before, but anyway. All right, these are functional groups. Alkyl halides have an R group, which is sp3 hybridized.
And okay, what do we mean by R? Okay, organic chemists are famous for using symbols. I told you before, a few minutes ago, that there are literally billions and billions and billions. of different organic molecules out there. And you can't draw all structures all at once.
So people have devised a symbol. This letter R stands for the rest of the molecule. I'm not sure if that's exactly why they chose the letter R, but that's how they use it for the rest of the molecule. As long as that is sp3 hybridized, that would be considered an alkyl halide because this R group would be like an alkane attached to a halogen. with the X letter being used for fluorine, chlorine, bromine, and iodine.
Here's an example, methyl bromide, and there's kind of a 3D structure, blah, blah, blah. Okay, alcohols have either an sp3, we're going to say technically an alcohol that our group is sp3. We're going to say there's another kind of alcohol where you have a benzene ring here, they call that a phenol. or a phenol, and that's slightly different than an alcohol. It's actually a different functional group, and she doesn't list it, but we will.
And in an exam-type setting, I'm not going to pit an alkyl alcohol versus an aromatic hydrocarbon alcohol, which is coldophenol. I'm not going to pit those two against each other. Not yet.
We'll learn about it more as we go along. This honestly is a little bit like learning a board game. It's got all kinds of subtle nuances and subrules.
different things. It's very complex. And so we'll just kind of give you the lay of the land, 30,000 feet, as it were, the best I can.
And then little details will crop up as we go along, little exceptions to little rules. And trust me, it'll all begin to gel as we go forward. All right. So here is an example of an alcohol.
This is methanol or wood alcohol. This stuff, if you drink 50 mils. It'll make you blind. 100 milliliters will kill you.
Used to be a lot of people in the U.S. would drink this. They'd see a can or a bottle that said wood alcohol on it. They'd think, oh, alcohol. I can get drunk. This one is very different from ethanol, which has a CH3 and a CH2.
That's the alcohol in alcoholic beverages. But anyway, anything that has an sp3 hybridized carbon here and a bunch of other stuff. This would be the functional group alcohol.
And all alcohols behave very, very similarly. Ethers are what I refer to as oxygen sandwiches, where the oxygen is the piece of meat, and you have two R groups, and R stands for the rest of the molecule. And this can be sp3 hybridized, as in this example. Or we could have an sp2 hybridized carbon over here.
So we could have an alkene type group or a benzene type group, and that would still be considered an ether. The main thing is you have an O here in between. I'm going to skip down really quick and show that the ether is very similar to the sulfide. Sulfide being a sulfur sandwich.
And again, you have sulfur being the meat in two R groups, either sp3 or... sp2 hybridized so here's an example with two sp3 hybridized groups ch3s yeah and so that is kind of the sulfur version of an ether it's called a sulfide okay back up here uh there's another functional group class called amines and amines um have an n with two h's and an r or an n with one h and two r's or an n with three r's okay you The R's here are not hydrogen. They are not hydrogen. They are something carbon, either sp3 hybridized or sp2 hybridized. And you can have with one R group or two R groups or three R groups.
Over here we have it with just one, and this guy is called methylamine. And amines react and behave very differently than other kinds of compounds. Kind of interesting.
We'll see in a few minutes there's an amine called putrescine. and an amine called cadaverine. And I'll give you three guesses what those two amines smell like. Cadaverine obviously smells like rotten flesh. And the reason rotten flesh smells like rotten flesh is because it produces an amine.
Amines as a group tend to smell like fish. In fact, what makes fish smell fishy is that they produce amines, and amines have that kind of fishy smell. Thiols are another functional group, where R here is not H.
It is an sp3 or an sp2 hybridized carbon, and then you have an sh here. Here's an example, CH3SH. These guys are also very smelly, and in fact, it's thiols that give rise to the smell of skunk scent.
So if you've ever smelled a skunk, you have smelled a thiol. And almost all of them smell at least that bad. And when you've been working with them in the lab, it's hard not to take that smell home with you. And we've worked with thiols from time to time in our lab.
And students say that their wives make them take their clothes off before they come in the house just about, or for sure take a shower and keep their clothes in an outside closet or whatever. So they're pretty stinky. The disulfide is a little bit different than a sulfide.
It has two sulfur atoms connected. These R groups are either sp3 or sp2 hybridized carbons. I don't know of any that would have sp. Is it sp3 or sp2? And here is dimethyl disulfide.
We see this group a lot in proteins. It's how the cysteine units in... proteins join together and hold the secondary structure, you know, the alpha helices and beta sheets and stuff like that. It can hold them together and give tertiary structure to a protein via these disulfide linkages. Yeah, it's kind of cool functional group.
All right, so that table was taken from your textbook, and there's more to come from the text as well. All righty, so this This table that I found on the internet calls the alkyl halides haloalkanes, and those are synonymous terms. And they even drill down further and they talk about fluoroalkanes, chloroalkanes, bromoalkanes, and iodoalkanes. I'm not going to ask you to know those specific ones, just use the term haloalkane, or as she says back here, alkyl halide.
Those are equivalent or synonymous terms, which reminds me of a question. It goes, is there another word for synonym? And apparently there is.
I can't remember what it is, but there is another word for synonym, which kind of cracks me up. That's a joke. All righty. So haloalkanes, that's the same thing as an alkyl halide.
And don't worry about classifying them as to whether or not they're fluoroalkanes, chloroalkanes, bromalkanes, or iodoalkanes. But you might see these as you move forward in different places, different. papers you may read or something like that in your future. All right, we talked about alcohols already.
We have the ROH. Oh, here's a new one, ketones. Okay, so ketone is the functional group. Okay, and a ketone contains a carbonyl. Okay, that word right there, a carbonyl is just a carbon and a double bond O.
That group right there is referred to as a carbonyl. It is not a functional group. Okay.
It's a piece of a functional group. And I don't know, honestly, what the accepted designation of it is. You can call it, more likely they would use a word called, people would use a word moiety, which is a fancy word for piece.
Okay. But you should know that a carbonyl is a C double bond O, and it's found in ketones and aldehydes. Aldehydes have a carbonyl.
And so do ketones. The difference between a ketone and an aldehyde is ketones have two non-hydrogen groups on either side of the carbonyl. Okay, R prime means that it's different than R. Okay, or they could be the same.
Like acetone, for example, the stuff you use in fingernail polish remover. That's two CH3s. Okay.
And yeah, so anyway, acetone is a ketone and these two R groups could be the same or they can be different. Acetone is also used in priming PVC pipe. If anyone who's ever laid sprinkler pipe, you take and you put that kind of blue stuff or that purple stuff on the pipe to soften the plastic. It's actually acetone.
It's just kind of starting to not actually melt. It actually starts to dissolve the PVC. plastic. Then you put on glue, put the two pieces together, hold it for a while, and you got this bond between two pieces of pipe that's as strong as the pipe itself. Okay.
Alrighty. So ketones, again, the word ketone, you have up to two different R groups, but they must not be hydrogen in order for this to be a ketone. With an aldehyde, okay, the aldehydes differ from the ketone in that you have one R group and one hydrogen.
Okay. Now I'm going to warn you that later on, in a later chapter, we're going to see that there is a molecule that's considered an aldehyde, that both of these guys are H's. Okay, that's the most simple aldehyde of all.
It is called methanal, derived from methane. Hence the name methan. It's derived from methane.
Methanal has two H's. But otherwise, all the rest of them, every aldehyde except... Methanol has a non-hydrogen thing here, carbon sp3 or sp2 hybridized carbon and whatever else attached. Okay, here's an example, acetaldehyde where we have a CH3, a carbonyl, again that's a carbonyl group, and an H attached. Okay, those are the aldehydes.
Acyl halides look like this. You have an R bound to a carbonyl. This can be sp2 or sp3.
And you also have a halide attached to the carbonyl. This can be, in practice, chlorine, bromine, or possibly iodine. Most likely, the only ones I've seen commercially available have chlorines attached.
And this would be a great reagent for making aspirin, for example. There's a related reagent, which I'll show you. later and you see probably in 352 but anyway yeah that's where we see acyl chlorides okay perfect carbonates i'm not going to hold you to that in in any exam we give in 351 but you should be aware that they look like this you have a carbonyl and two ors you get or1 and or2 where r is not hydrogen okay you It's sp3 or sp2 hybridized carbon.
Okay. Carboxylates. I actually wouldn't make this its own functional group.
Most textbooks and most practicing organic chemists would say that a carboxylate is just a deprotonated carboxylic acid. And that's true. Okay. So don't worry about this one, nor this one. But carboxylic acids look like this.
We have an R bound to a carbonyl and an oxygen. Okay. R, carbonyl oxygen, and an OH attached to the same carbonyl carbon.
You have a carbonyl and an OH. This must be, for the most part, sp3 or sp2 hybridized carbon. Now, this is an example that later on, we'll see in a later chapter, that there is one carboxylic acid where R is an H. And it is derived from the most simple carboxylic acid of all called methanoic. acid, okay, named after methane because it has one carbon in it, methanoic acid.
In that case, R can be an H, but ordinarily, for all the rest of the carboxylic acids, R is not H. It is either an sp3 or an sp2 hybridized carbon. Okay, esters.
Esters have a carbonyl, okay, attached to an OR. They look an awful lot like a carboxylic acid, and in fact, they are made from carboxylic acids. And we will learn in 352 how you make esters from carboxylic acids. And we don't have to worry about that right now, but the difference between a carboxylic acid and an ester, take a look at it and think about it. If you were to explain to your neighbor how these two differ, what would you say?
You see it? The carboxylic acid, you have an H on the O. Here you have an organic piece.
either an sp3 or sp2 hybridized carbon and it can either be the same or different than that r group okay This one cannot be H, or if it is H, it's a carboxylic acid. That one could be an H for the most simple ester of all derived from methanoic acid. Okay.
All righty. Let's press on. I disagree with this.
Let's scratch that out. In fact, for the most part, other than ethers. I wouldn't worry. We'll see peroxides later and hydroperoxide later.
This is not really a functional group. So let's kind of back burner those. Don't worry about those. But ethers, we talked about before, they're oxygen sandwiches where the R groups are SP2 or SP3 hybridized, and they can either be the same or they can be different.
Diethyl ether is a very commonly used ether. It used to be used as an anesthetic. in surgeries but it can cause pneumonia it kind of condense causes water to condense in the lungs and so they stopped using it it's also flammable and it's very highly volatile it can fill an operating room with fumes and if you drop something and it sparks it gets a lot warmer than you thought it was going to be so okay so disregard these top three ethers you should know and amides We already talked about in the slide from your textbook, or table from your textbook, did we? No, we talked about amines. Amides we've not yet talked about.
Okay, amides are sort of like esters, but they have a nitrogen here instead of an oxygen. Since the nitrogen can take on up to two other things on the nitrogen other than hydrogen, you can have up to a total of three algorithms, one here, one there, one there. These can be hydrogen, or they can be SP3 or SP2 hybridized carbon. So this one's kind of a little bit complex, right?
This is what I was saying about the subtle nuances, and bear with me. I'll show you some examples, and this will begin to make more and more sense as we go along. But the key thing here is you have a carbonyl attached to a nitrogen. That's what you're looking for in the amide. The nitrogen is attached to the carbonyl carbon, and that nitrogen can have two hydrogens, or two R groups, or one R group and one hydrogen, and the R groups don't have to be the same, nor does that have to be the same.
Okay? We talked about amines. When an amine has one R group, they call it a primary amine.
When it has two R groups, they call that a secondary amine. When it has three R groups, they call that a... tertiary amine, and when it has four, one, two, three, four, they call that a quaternary ammonium ion. We'll learn more about these in chapter 25 and 352, so for now, just worry, be aware of the name amine, and in an exam type setting for 351, you would be asked to classify these guys just as amines and not worry about whether or not one's primary, secondary, tertiary, or quaternary.
Okay, thiols we talked about already. One non-hydrogen R group attached to an SH. Sulfides are like a thioether. Two non-H R groups, the sulfur sandwich, the sulfur in the middle, etc., etc.
Okay. All right, this actually is, I think, scanned. I think I scanned this out of your textbooks.
It's in the flyway for the textbook. And I want to make the point here again, this is not right. That's not the type of compound. It's the functional groups.
I put the functional group over here. Okay, and this is just a piece of the functional group But you've got acyl chloride so look like that you have don't worry about these. Okay, we're gonna ignore that That's what you find in like ATP or Yeah, any phosphorylated Biomolecule alcohols we talked about aldehydes we talked about alkanes, alkenes, acyl halides, alkynes, amides, amines, anhydrides we didn't yet talk about, and we will eventually. But an anhydride has essentially two carbonyls attached via an O.
So it's a little bit different than an ether. It's almost like an ether. And here's... Where's the ether? Ether has two R groups sandwiched on either side of the O.
So does this, but if you have a carbonyl, two carbonyls on either side of the O, that gives us a very different kind of reactivity, and so it warrants its own functional group name, which is anhydride. Aromatic hydrocarbons we talked about. Carboxylic acids we talked about, okay, where this R can be SP3 or SP2 high-rise or an H.
Disulfides, it's two R groups, non-hydrogen, neither side of two sulfurs. Esters, we have the R and a carbonyl OR. Here's an example.
Ethers, oxygen sandwiches, ketones, both of these R groups must be non-hydrogen. If one of them is a hydrogen, it's an aldehyde. If both are hydrogen. it's also an aldehyde, and the aldehydes are shown over there.
Okay, don't worry about the monophosphates. Okay, nitriles, I won't cover in the first exam, something we cover in 352. Sulfides, you ought to be aware of. They are, again, sulfur sandwiches, very much like ether's thiols, and they're very stinky, smell like skunks, and the bottom one I can't see because my zoom thing's on top of it. And, um, so, oh, it went away.
Thank goodness. Thioester. Okay. Um, it's very similar to a, uh, an ester, but it has a sulfur right there.
Okay. Alrighty. Uh, not to beat a dead horse.
It's just going to review the tables. She has the textbook, the hydrocarbons. There are four kinds of hydrocarbons. There are the alkanes with no double bonds, alkenes with two double bonds, alkenes with three double.
With a double bond in the alkene and in alkyne, you have a triple bond. Aromatic hydrocarbons have this six-membered ring with alternating double bonds. And yeah, okay. Alkahalide, we already talked about. We've already seen this slide before, so I'll skip through it.
Same thing here. I just refer you to your text, and I would encourage you to make flashcards. Okay. Now.
I went through and made a bunch of examples on my iPad a few years ago, and these are incorporated here just to kind of give you some examples of alkanes. There are a bunch of them here. Take a look at them.
Methane, ethane, propane. What is this? Three of this.
Five. Pentane, hexane, blah, blah, blah. Ane.
All these long-chain alkanes, branch-chain alkanes like this. As long as you don't have double bonds and all you have is carbon and hydrogen, they call that. and alkane.
Alkenes have at least one carbon-carbon double bond. This one has three, so that would be called a triene. We won't hold you to that quite yet. This one's called a diene.
Bottom line is you have to have at least one, and it cannot be cyclic. If it's cyclic and you've got three alternating ones like this, you've got an aromatic hydrocarbon. So if you have three or more, it can't be cyclic or it would be aromatic hydrocarbon.
So take a look at all these. They all share in common the fact that they have one double bond. It doesn't matter what else is on there if you have fluorines.
Okay, so technically, some people would say this is not a hydrocarbon because you have more than hydrogen and carbon, but you can also call it an alkene. Okay, so here's an alkene, here's an alkene, here's an alkene. It's a halo-substituted alkene.
But people wouldn't really expect you to differentiate in an exam type setting. If you see something like this, classify it as an alkene. Alkines have carbon triple bonds. You can have settling, the most simple one.
This one's called a terminal alkyne. This one's called an internal alkyne, where you have two R groups on either side. Here's an example of an internal alkyne. Here's another internal alkyne.
terminal alkyne. A terminal alkyne has a CH. H is either going to be explicitly drawn or implied. More often than not, it'll be implied and not explicitly drawn. Here's an implied one.
There's an implied one. There's an implied. So there's a CH implied at the end of each of these.
Okay, that's something a lot of people miss when they start out, is if I draw it like this, a lot of textbooks don't make it very clear, and I guess I haven't made it very clear as an instructor either. that all of these have a CH that's implied. There's an H there, there's an H there, H there, H there, H there, H, H. That would be formally a diine, but right now at this level in 351, we're not going to call it that. We're just going to say it has two alkyne functional groups in it, as does this one. Yeah, and alkynes share in common the fact that they do.
many, many things similar to one another, okay? They behave or function similarly to all other alkynes. That's why they're in this alkyne functional group.
Aromatic hydrocarbons, basically you have a benzene, a six-membered ring with alternating double bonds. Here's an example of benzene. It's got an alkyl group, an alkane attached here. In an exam-type setting, I'm not going to ask you to identify the alkane.
For our purposes, the alkane is kind of the entry level. It's like all organic molecules could be viewed as derivatives of alkanes. So you start with alkanes, and then you start... adjusting them and modifying them.
And so an exam type question, I would not ask or even suggest that you call that an alkane because it's kind of understood. Yeah, of course it's an alkane, but this is the more interesting, unusual piece of it. Okay.
So we're going to consider the whole thing an aromatic hydrocarbon for the purposes of this exam. Okay. The whole thing we're going to consider an aromatic hydrocarbon, although technically this piece right here, if we were to cut it off. would be an alkane type hydrocarbon, but we're going to consider the whole thing an aromatic hydrocarbon, okay?
All right, so there's a whole bunch of them. Doesn't matter what else you have attached to the benzene. We're going to consider this whole thing as an aromatic hydrocarbon for now in terms of identifying functional groups. And it turns out that the benzene does a lot more interesting things than an alkane does as far as its reactivity is concerned.
So it's... Kind of an interesting beast. It allows you to modify it much more readily than the alkane allows you to. And yet it's in some ways lower in energy than the alkane. We'll come back and talk about that in Chapter 18 in Chem 352. All right.
Alkyl halides, again, we talked about. You have an R group attached to a halogen. The halogens are fluorine, chlorine, bromine, or iodine. and typically the R group is sp3 or yeah I guess for me alkyl halide it must be sp3 hybridized so here's some examples take a look at them okay so they have all these different alkyl groups or alkanes attached to the halogen a whole bunch of different ones there okay alcohols you have an R group attached to an OH, and technically this R group must be SP3 hybridized in order for this to be considered an alcohol. There's another kind of alcohol with an SP2 hybridized carbon, basically a benzene, and that's called a phenol.
It's a special kind of alcohol, but for our purposes, I'm going to go ahead and in an exam, I will let you call a phenol. I'll let you classify that as an alcohol, although technically it's a special kind of alcohol, and if you really want to drill down and get uber specific about it. Phenol is very different from an alkyl alcohol.
Okay. So methanol and what alcohol, ethanol is in, you know, alcoholic beverages. Isopropanol is the stuff that you use in hospitals.
Okay. When they say, give me some alcohol, that's what they're talking about. Okay.
Generally speaking is rubbing alcohol is that stuff right there. I guess they say they could be asking for ethanol. I think there are definitely medical purposes uses for this guy. Okay. But rubbing alcohol is that.
Anyway, just gives you some idea of some of the possible alcohols. Okay. Here's the phenols.
All right. Phenols have a benzene attached to the OH, and technically they are their own distinct functional group. I will not pit a phenol against a non-aromatic. I'm not going to pit those two against each other right now. For right now, all I care is if you see an OH attached to a carbon that doesn't have a carbon-oxygen double bond.
If there were carbon-oxygen double bonds here, that would be a carboxylic acid. As long as it's attached to an sp3 hybridized carbon like these guys are, that's an alcohol. If it's attached to an aromatic ring, I'm going to be okay with you calling this an alcohol for now, but technically it is a special kind of alcohol called a phenol, and it has actually very different properties from... that kind of alcohol.
Specifically, it is a million times more acidic. That OH is 10 to the 6 times more acidic than that OH, and that makes a big difference in how this behaves. In fact, it's quite interesting that in poison oak, the compound that makes you itch actually has two OHs, and that's part of what makes you itch is it's so acidic that it gives you some localized acid concentration and and that's one of the reasons your body reacts to it but anyway here's some examples of phenols notice we can have the benzene with all kinds of different things attached ch2 ch3 ch3 that group right there blah blah blah okay there's your phenols Okay, cool.
Ethers. The oxygen sandwich with two R groups, one on either side. We've got, this is called dimethyl ether.
This is methyl ethyl ether. They don't have to be the same R group, right? They can be like this guy, which is a 1, 2, 3 propyl group.
Here's a cyclohexyl group. Benzene attached to an O. Two of these cyclohexyl groups, cyclopentyl groups. Two benzenes. blah blah blah etc etc okay that's kind of the general thing you're looking for in an ether sulfides are like sulfur versions sometimes some people call them phyo ethers and they're very similar in fact i think when i made these i just i just take yeah i did i just took with my my um apple pencil and erased the o and every one of these yeah and replaced them with sulfur and Yeah, just that easy.
Okay, those are called sulfides. Disulfides, you have two sulfurs bound together, and we see these a lot in proteins. I said before, the cysteine units in proteins undergo an oxidation reaction, form a disulfide linkage, and the secondary structures are such as alpha helices and beta sheets and so forth there. joined together at different places by these disulfide linkages forming between cysteine units. Thioesters are very similar to esters.
You have a carbonyl and an SR. Okay, so carbonyl R, SR prime. Here are some examples.
Okay, look at these with me. I know you can see them probably as well as I can point them out to you, but I'm trying to lead your eye with the pen. Here's your R group, carbonyl, SR, carbonyl, R group.
SR that our groups are tethered together carbonyl our group tethered to the other are on the s Here is a carbonyl R and SR prime carbonyl R SR there's a R prime. Here's your R carbonyl SR prime our carbonyl s our prime that's one I should have done that before our carbonyl Sr prime. Okay.
And here's an example. Sometimes for esters, that R group can be an H. R carbonyl Sr prime, R carbonyl Sr prime, R carbonyl Sr prime. So sometimes you can have an H at this position.
Okay. So R can be H for the thioesters. For regular ester, you have an oxygen.
Attached to the carbonyl. We have an R carbonyl. Oh our prime. Here we go our carbonyl Oh our prime our carbonyl yeah, Oh our prime our carbonyl Oh our prime our carbonyl Oh our prime our Carbonyl Oh our prime the our primary are are tethered together in this case our carbonyl O, R prime. The R and the R prime are tethered together.
Here we have it written backwards. Okay, I've just flipped the molecule. Here is my R, my carbonyl, O, R prime.
So what I'm trying to show with this one is that the writer of an exam or whoever writes the scheme isn't always going to write it in this direction. You could just flip that molecule 180 degrees, which I've done here. Here's the R prime group. the O, the carbonyl, and the R. So this has been flipped 180 degrees.
So there's no convention. It requires that you write it in that direction. You can flip this and have the R prime first, then the O, then the carbonyl, then the R, as I've done here.
Yeah. Think about that. Okay. R, carbonyl, O, R prime.
R, carbonyl, O, R prime. R, carbonyl, O, R prime. And then you can have an H in place of an R for the esters. It's the only, one of the few functional groups where you can have something non-carbon here, okay? You have H carbonyl OR prime, H carbonyl OR prime, there's our prime, H carbonyl OR prime, okay?
So there are several esters for you to look at. Amides, similar to esters, remember the ester we had, the R carbonyl OR prime. Here we're going to have in the amides R carbonyl N, R prime, R double prime.
The R's can be carbon organic pieces or they can be hydrogen. Okay, so here we go. R, carbonyl, carbonyl actually is not a functional group.
The whole amide, this whole piece right here is the functional group, the amide, the carbonyl. And the fact that it's got an R over here. So anyway, that's the functional group carbonyl. And in this case the R prime and R double prime are the same. Okay.
R prime and R double prime. They don't have to be different. They can be the same.
Okay. R carbonyl and R prime, R double prime. Okay. R prime and R double prime are different this time.
Okay. See how they're different? This is called a methyl group. That's called an ethyl group. We'll come back to that later.
Here's our R group attached to the carbonyl and R prime, R double prime. They are two different R groups. R carbonyl, N, R, R prime rather, R double prime.
Carbonyl, R, N, R prime, R double prime. The R prime and the R are connected in this case. This is a cyclic amide, also called a lactam. I'm not going to hold you to that nomenclature.
We'll learn that later in 352. You've maybe heard of beta-lactam antibiotics like penicillin. Beta-lactam antibiotics have not a six-membered ring, but a four-membered ring. They are cyclic.
They are amides. And as part of how penicillin works is by the reactivity of the cyclic amide, which we call the lactam. Okay, R carbonyl and R prime, R double prime.
In this case, the R and the R prime are joined together. I've flipped it now. And again, I want to make the point that it doesn't have to be written in this direction. We can flip that 180 degrees.
It's still an amide, right? Here is the R group. Here's the carbonyl.
Here's the N, R prime, R double prime. It turns out that R prime and R double prime in this case are the same, and that's okay for it still to be an amide. And so on and so on. So I won't bore you with all the details. I think you're getting it.
Sometimes the R group can be an H, just like with esters. and thioesters and carboxylic acid, this group attached to the carbonyl can be an H, and we'll learn more about that in chapter, in 352. Okay, so yeah, this is H-carbonyl, N-R-prime, R-double-prime, they're the same this time, H-carbonyl, N-R-prime, R-double-prime, blah, blah, blah, et cetera, et cetera. One of the things I don't have here, do I have it, I hope? Oh yes, I do. Okay, so these groups on the nitrogen can also be hydrogen.
I think what I did here was just took this whole thing and lassoed it with my iPad and cut and paste it. And so these are the same examples, but what I've done is I've removed the R double prime and replaced it with an H. Okay, so this is also an amide.
That's an amide. all these are amides. The point is that that does not have to be a non-hydrogen thing. It can be hydrogen.
In fact, they can both be hydrogens. And I think I did that again, cut and paste. And, excuse me, lassoed and cut and paste.
So both of the groups on nitrogen can be hydrogen for an amide. So all of these are examples of amides. R-carbonyl N2Hs, R-carbonyl N2Hs, R-carbonyl N2Hs, et cetera, et cetera.
Now, again, like the esters, the thioesters, and the other examples of amides, this can be an H, and that would still be considered an amide, and we'll learn why in 352. Okay, all right, pause this anytime you want, and look at it, and then we'll go on. Okay, amines are similar to amides, but... they don't have a carbonyl. What you're looking for for an amine is you're looking for the absence of that group. You do not want a carbonyl in an amine.
In fact, if you have the carbonyl, it's an amide, not an amine. That's the difference. So an amine can have one R group attached to the N and two Hs. So here's our R group, N, two Hs.
R group, N, two Hs. R group, N, two Hs. R group, N, two Hs.
R group. and two H's our group and two H's to the two H's and the our group you can flip it don't have to write it that direction. You could have your R group off your other right. R group and two H's, blah, blah, blah, blah, blah. Okay.
That's a special kind of amine. I think we have other kind of amines. We do.
Okay. That's called a primary amine. There's a secondary amine where you have two R groups and one H, two R groups, one H, two R groups, one H, two R groups, one H, two R groups, one H, all attached to the nitrogen.
R-group, nitrogen, R-group, H. Okay, R-group, R-group, nitrogen, H. R-group, R-group, nitrogen, H. They can be written in different orders.
Okay, you can have them kind of like this relative to each other or another side. That doesn't matter. Okay, whether they're on the other side of the nitrogen or down there, or you can even flip the molecule to where you draw the H first attached to nitrogen, then the R-group and the R-group, etc. These are called secondary amines. Okay?
Okay, look at those. Think about them. Secondary amines.
Here are tertiary amines with three R groups, and you can write them in any order. Just take a look at them. I don't want to confuse you with the pointer. Every one of those nitrogens has three non-hydrogen things attached to it.
Every nitrogen has three non-hydrogen things attached to it. That's the telltale sign of a tertiary amine. Okay, carboxylic acids.
R turns out can be an H. This is formic acid. And why I wrote that three times, I don't have the slightest idea.
I don't know what I was thinking, guys. I apologize, okay? But you get the point, right?
So I've written it three times. And so that definitely... It's three copies of the same carboxylic acid, and its name is methanoic acid. And it is the most simple carboxylic acid of all.
What's interesting is it's actually derived from the jaws of ants. And I laugh every time I think of it. I think to myself, what's sicko out there?
We'd go gather up together enough ants and boil them in water. That's what they have to have done to get this. Boil a ton of ants. I guess it depends on how mad you are at your ants and how serious you are about getting rid of them.
the, you know, I guess if you're Terminex or any of these other pest control companies, you know, you want to get rid of ants, right? So anyway, that's where that comes from. It's from the jaws of ants.
And it is called methanoic acid, okay? Or formic acid is another name for it. That's the Latin name, formic acid. And it's when an ant bites you, that's what stings, okay?
Now you know, right? Inquiring minds want to know. and now you do.
Okay. All right. But most carboxylic acids have a non-hydrogen attached to the carbonyl and the OH. Non-hydrogen attached to the carbonyl and the OH.
This guy is acetic acid. This is found in vinegar. When you eat vinegar on your salad, that's what you're eating.
That stuff right there. Okay. Most of you have eaten plenty of this in your lives. Benzoic acid, okay, has a benzene attached to the carbonyl and the OH.
This stuff is found in soft drinks. You read... a can of any of your cans of soda. I don't care what it is.
It's Coca-Cola or 7-Up or Sprite or you name your soda and it has sodium benzoate. It's actually the sodium salt of this where you pulled off the hydrogen, put a sodium in its place, but the parent for sodium benzoate is benzoic acid. I don't know about you guys, but I drink my fair share of soda and I have had plenty of this in my lifetime.
R group carbonyl OH, R group carbonyl OH, R group carbonyl OH, etc., etc. And, okay, so here's an example that for our purposes, we're going to still call this a carboxylic acid, even though it's attached to a nitrogen, okay? This part of it is a carboxylic acid.
That part of it's an amide. That's got both functionalities in the same molecule. I will not do that to you in an exam. Okay, I'm not going to ask you to which one should take precedence, but this has both an amide on this side.
That would be considered an amide, yeah, and this would be considered a carboxylic acid on that side. Okay, we get that twice. Okay, that twice, and this one's different.
Okay, acyl chlorides. You have an R carbonyl and a chloride. And obviously, if you want to stop this one and take a break, this is getting kind of long. But I'm going to get through it and do it maybe in one fell swoop here. And you can come back and listen to it in pieces.
Okay, R group, carbonyl, Cl, R group, carbonyl, Cl, R group, carbonyl, Cl, R group, carbonyl, Cl, R group, carbonyl, Cl, blah, blah, blah. Here we have an NH2 and a carbon in a Cl. It would still be considered an acyl chloride, this side of it.
This side would be considered an amide. I won't pit these two against each other in an exam type setting, just so you're aware of it. In fact, this probably isn't a very good example because that probably wouldn't exist very long, probably transient intermediate, so kind of forget that one. This one we've seen before up there, this one there, this one's new, and I do that one three times.
I, again, must have been tired when I made these. My apologies, okay? What do I say every time I'm trying to excuse myself?
Eva Moroni drops his trumpet every once in a while, right? Okay. You'll probably be tired of hearing me say that by the time this is over.
Okay, aldehydes, R, carbonyl, H. The R group in this case can be H. And there it is.
That's the most simple aldehyde of all. It's called formaldehyde. or methanal okay h carbonyl h that is an aldehyde but other than that one the rest of them have to have a non-hydrogen thing like a ch3 a carbonyl or an h a c3 ch2 carbonyl or an h r carbonyl h i didn't say i didn't mean r or h r carbonyl h r carbonyl h r carbonyl h r carbonyl H. Here's your whole R group carbonyl H, R group carbonyl H, R group carbonyl H, R group carbonyl H, et cetera.
Okay. All righty. So this has gone about an hour.
I don't want to get it too much longer than an hour. I'm afraid it may not save properly. So I'm going to go ahead and close out at ketones and let's maybe page ahead.
Yeah, well, let me finish ketones, and then we'll start up with part two of unit two, which is actually chapter three in the Smith textbook. All right, ketones are very similar to aldehydes, except for both of these R groups cannot equal to H. That's the difference between a ketone and an aldehyde.
The R groups cannot equal to H. I'm going to say that about three times, because this is a very commonly missed point for beginners, okay? The r group cannot be a hydrogen okay the r groups cannot be hydrogens so we have a carbonyl so let's do r group carbonyl r group r group carbonyl r group r group carbonyl r group r group carbonyl r group r group carbonyl r group and i should put a prime up here to indicate that these can be different from one another or they can be the same.
So this is an example of what we call a symmetrical ketone. There's a plane of symmetry here, and what's over on the right hand side is the same on the left. We call that a symmetrical ketone. When they aren't the same group, they call it an unsymmetrical ketone. I think all of the rest of these are all unsymmetrical, because the only symmetrical one we have here, this R group is different than that one, this R group is different than that one, that R group is different than that one, that's different than that one, that's different than that one.
Bottom line is you have a carbonyl and two R groups. These cannot be hydrogens. If one is a hydrogen, okay, actually if one or both are hydrogen, we're looking at an aldehyde, okay?
If one or both of these groups are hydrogen, like in this case both are, okay, that's an aldehyde. It's the only aldehyde that has two Hs. The rest have one R group and an H.
One R group, H. One R group, H. Blah, blah, blah. Okay, ketones.
two R groups, one on either side of the carbonyl. They cannot be H. Okay, I would encourage you to make some flashcards.
And I think probably the most helpful thing out of all these slides are these ones I've done by hand. And what I'd recommend you do is just go ahead and the red thing, yeah, make that be one side of your flashcard. And the back side, just put some of these examples and just quiz yourself.
Go over these a few times and remind yourself of the different functional groups. And, you know, it's good to look at these tables. That helps too.
And then I've got a handout that will be on Learning Suite. And I know for sure that the key for this is on Learning Suite. I'll put the blank, this part here on Learning Suite. The assignment for you to think about with a handout is what are the functional groups present in these really cool molecules. These are awesome molecules.
We're going to come back and talk about them more next time. But look at these and think about them. And it's almost 1130 p.m.
I'm going to shut this out for a second. turn this back into a arrow. I'm going to come over and in my Zoom thing, I'm going to stop recording.