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From Wikipedia, the free encyclopedia

Isopropyl group
Isopropyl group
Methyl group
Methyl group

In organic chemistry, an alkyl substituent is an alkane missing one hydrogen.[1] The term alkyl is intentionally unspecific to include many possible substitutions. An acyclic alkyl has the general formula of CnH2n+1. A cycloalkyl is derived from a cycloalkane by removal of a hydrogen atom from a ring and has the general formula CnH2n-1.[2] Typically an alkyl is a part of a larger molecule. In structural formula, the symbol R is used to designate a generic (unspecified) alkyl group. The smallest alkyl group is methyl, with the formula CH3−. [3]

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  • ✪ Naming alkanes with alkyl groups | Organic chemistry | Khan Academy
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  • ✪ Alkyl groups

Transcription

So far we've dealt with simple chains and rings of carbons. But let's think about what happens when things get a little bit more complex. Let me just draw a molecule here and we can think about how we'll name it. So let me draw it like that. So here we don't have a simple chain. It branches off at some point. So what we do in this situation is we find the longest chain in this molecule, and let's think about what the longest chain is. If we start here we get one, two, three, four, five, six, seven, eight carbons. If we start here we get one, two, three, four, five, six, seven, eight, nine carbons. So what we do is we look at the longest chain. The longest chain is this one right here. Let me do this in a different color. So this is one, two, three, one, two, three, four, five, six, seven, eight, nine carbons. And so this will be-- that will be kind of the core of our naming. So it's nine carbons. So that right here, longest chain, has nine carbons. You can kind of view this is the backbone of our molecule and also the backbone of our naming. Nine carbons, so we're dealing with a nonane. Remember, nine, non- for nine, and then -ane, because we're dealing with an alkane. We have all single bonds over here. Now, what do we do with this thing over here? Well, what's kind of sticking off of this chain? Well, we essentially have one carbon here that's attached to the chain, right? This carbon is bonded to a carbon on the chain. If we wanted to draw the entire molecule, we could draw carbon here and it would it be bonded to three hydrogens, but that is all implicit. But what is this thing right here? Well, it's one carbon. You might be tempted to say it's methane, but it's not methane because it's attached to other things. But it would be right to use the prefix meth-. So this right here, you would use the prefix meth-, so this is one carbon, so you would want to use the prefix meth-, but because it isn't the main chain, it is added to something else, we don't write methane, we write methyl. So let me write this right here: methyl. So this means it branches off longer chain. So this molecule right here would be called-- and actually, there's one more thing that we have to think about. This thing could have been-- we could just call it methylnonane. Let me just write that down right now. So we could just call this right from the get-go, we could call it methylnonane. But there's one problem with just calling it methylnonane. This is methylnonane, but so what's-- let me draw it. So the thing I just drew here, this is, one, two, three, four, one, two, three, four, five, six, seven, eight, nine. So that's the nonane. And the one I drew here's one, two, three, the methyl is right over here. That's what I just drew. That is-- let me do it in the same color. So this is what I just drew. But maybe, what if it was something like this? What if it was one, two, three, four, five, six, seven, eight, nine? And let's say that the methyl group was, instead of being right here, let's say the methyl group was right here. So how would you name these two things differently? This name right now does not differentiate between the methyl group being on this carbon versus the methyl group being on this carbon over here or this carbon over there. And what you do in this case is you number the carbons on the longest chain, on the main backbone, and you number them so that the methyl group is attached to the lowest possible number. So there's two possible ways to number this chain. You could start here as one, two, three, four, five, six, seven. Then you would say that this would be that the methyl group is attached to the seven carbon. Or you could start numbering from this end of the chain. It would be one, two, three. Or so it could also be attached to the third. Three, four, five, six, seven, eight, nine. So you want to number it so you're closest to the methyl group. So you want to start here. One, two, three, four, five, six, seven, eight, nine. So in this case, this would not just be methylnonane. This thing right here would be three. Let me make this very clear. It would be 3-methylnonane. Because the methyl group, that one carbon, that one CH3, is attached to the third carbon on our nonane backbone, so that right there is 3-methylnonane. Since I drew this out, what is this right here? Well, once again, we have this nonane backbone, one, two, three, four, five, six, seven, eight, nine, and you want to number it so that this methyl group is at the lowest number carbon as possible. So it's closer to this end than that end. So it's one, two, three, four, I'll do that in magenta, and you can keep numbering, five, six, seven, eight, nine. So this one is going to be four, and then you have your methyl group. It's just one carbon sitting right there, so 4-methylnonane. Now, let's go the other way around. Let's say we start with the name and we want to figure out its formula. And hopefully, this gives you a good understanding how things will get more complex. And over the next few videos, they'll get more and more complex, but you'll see it's all at least reasonably logical. So let's say I were to give you let me think of one. Let's say 2-propylheptane. So how do we take this apart? So the first thing you see, it is an alkane. It's all going to be single bonds. Heptane, this is kind of the core. So the longest chain here, hept- is the prefix for seven. So this tells us-- let me make this clear. This tells us that we're dealing with all single bonds. That's what the -ane tells us. If we had double bonds, it would be -ene, triple bonds, -ine. We're going to see that in the future, but let's stay simple right now. The hept- tells us we're dealing with seven carbons. And then what does this 2-propyl mean? Well, propyl tells us-- what was the prop- prefix? If methyl is one, ethyl is two, propyl is three, butyl is four, so this is a three-carbon group, and it's going to be attached to the second carbon on the heptanes. Let me draw the heptane chain. So we have seven carbons, so one, two, three, four, five, six, seven. And then on the second carbon-- just let me pick a good color here. On the second carbon, so if we just number it one, two, three, four, five, six, seven, on the second carbon right there, we have a propyl group. We have a propyl group, but it is a three-carbon group. So let me draw the propyl group. So we have a one, two, three, three-carbon group, and it's attached at the second carbon right there. So this molecule, 2-propylheptane looks just like this. Let's do another one, maybe one that seems a little bit more difficult. Let's say that we have 6-butyltetradecane. And all of these might seem a little daunting when you see it at first, but if you really just break it up, it actually is pretty logical. So once again, we have the -ane there, so it's all going to be single bonds. What is tetradec-? What is that prefix? Well, dec- is 10 and then we have tetra-, that's 4 plus 10, that's 14. Tetradec- is 14. So this is telling us that we're dealing with a 14-carbon chain. Let's draw that. So one, two, three, four, five, six, seven, eight, nine, ten, eleven, twelve, thirteen, fourteen carbon chain. And if we number them, one, two, three, four, five, six, seven, eight, nine, ten, eleven, twelve, thirteen, fourteen, this tells us that the sixth carbon will be butyl, will be a butyl group. So let's see, the sixth carbon is right here. And butyl, and you should memorize this, methyl is one, ethyl is two, propyl is three, butyl is four, so we have a four-carbon group. So let me write this in a pink maybe. So this is a four-carbon group. When you call it an alkyl group, it's attached to something else. So on the sixth carbon, we have a four-carbon group, so one-- let me draw it this way. No, this is fine. Let's say we have one, two, three, four, so that is our butyl right there, and it's attached to the sixth carbon. It's attached to the sixth carbon right there. So this is what our molecule would look like. Now, let me ask you a question. Would you ever see a 9-butyltetradecane? Would you ever see a 9-butyltetradecane? So something where-- so let me redraw it like this. So a 9-butyltetradecane, so it would have butyl over here. One, two, three, four, one, two, three, four. Would you ever see a 9-butyltetradecane? Will you ever see that written? You might say, oh, yeah, Sal, you just drew it. And the reason why you won't ever see that written is because there's a better way to number it if it's like this. Instead of starting over here at one at this end, you'd want to start one that end. So instead of saying 9-butyltetradecane, you should number it the other way. You should say this is one, two, three, four, five, six. So this is actually also 6-butyltetradecane. Let me be sure I got that. One, two, three, four, five, six. So instead of starting from the left and making this the ninth carbon, you always want to start numbering from the direction that has the lowest number for the first group.

Contents

Related concepts

Alkylation is an important operation in refineries, for example in the production of high-octane gasoline.

Alkylating antineoplastic agents are a class of compounds that are used to treat cancer. In such case, the term alkyl is used loosely. For example, nitrogen mustards are well-known alkylating agents, but they are not simple hydrocarbons.

In chemistry, alkyl is a group, a substituent, that is attached to other molecular fragments. For example, alkyl lithium reagents have the empirical formula Li(alkyl), where alkyl = methyl, ethyl, etc. A dialkyl ether is an ether with two alkyl groups, e.g., diethyl ether (O(C2H5)2). Alkyl also refers to an active ingredient in green algae preventatives used in swimming pools.

In medicinal chemistry

In medicinal chemistry, the incorporation of alkyl chains into some chemical compounds increases their lipophilicity. This strategy has been used to increase the antimicrobial activity of flavanones and chalcones.[4]

Alkyl cations, anions, and radicals

Usually, alkyl groups are attached to other atoms or groups of atoms. Free alkyls occur as neutral compounds, as anions, or as cations. The cations are called carbocations. The anions are called carbanions. The neutral alkyl free radicals have no special name. Such species are usually encountered only as transient intermediates, but some are quite stable and can be "put into a bottle". Typically alkyl cations are generated using super acids, alkyl anions are observed in the presence of strong bases, and alkyl radicals are generated by a photochemical reaction. Alkyls are commonly observed in mass spectrometry of organic compounds.

Nomenclature

Alkyls form homologous series. The simplest series have the general formula CnH2n+1. Alkyls include methyl, (CH3·), ethyl (C2H5·), propyl (C3H7·), butyl (C4H9·), pentyl (C5H11·), and so on. Alkyl groups that contain one ring have the formula CnH2n−1, e.g. cyclopropyl and cyclohexyl. The naming convention is taken from IUPAC nomenclature:

Number of carbon atoms 1 2 3 4 5 6 7 8 9 10 11 12
Prefix meth- eth- prop- but- pent- hex- hept- oct- non- dec- undec- dodec-
Group name Methyl Ethyl Propyl Butyl Pentyl Hexyl Heptyl Octyl Nonyl Decyl Undecyl Dodecyl


These names are used to name branched chained structures, for example 3-methylpentane:

The structure of 3-methylpentane is viewed as consisting of two parts. First, five atoms comprise the longest straight chain of carbon centers. The parent five-carbon compound is named pentane (highlighted blue). The methyl "substituent" or "group" is highlighted red. According to the usual rules of nomenclature, alkyl groups are included in the name of the molecule before the root, as in methylpentane. This name is, however, ambiguous, as the methyl branch could be on various carbon atoms. Thus, the name is 3-methylpentane to avoid ambiguity: The 3- is because the methyl is attached to the third of the five carbon atoms.

If there is more than one of the same alkyl group attached to a chain, then the prefixes are used on the alkyl groups to indicate multiples (i.e., di, tri, tetra, etc.)

This compound is known as 2,3,3-trimethylpentane. Here three identical alkyl groups attached to carbon atoms 2, 3, and 3. These numbers are included in the name to avoid ambiguity on the position of the groups, and "tri" indicates that there are three identical methyl groups. If one of the methyl groups attached to the third carbon atom were an ethyl group, then the name would become 3-ethyl-2,3-dimethylpentane. Note that when there are different alkyl groups, they are listed in alphabetical order.

In addition, each position on an alkyl chain can be described according to how many other carbon atoms are attached to it. The terms primary, secondary, tertiary, and quaternary refer to a carbon attached to one, two, three, or four other carbons respectively.

Etymology

The first named alkyl radical was ethyl, named so by Liebig in 1833 from the German word "aether" (which in turn had been derived from the Greek word "aither") (https://en.wiktionary.org/wiki/ether , i.e., the substance now known as diethyl ether) and the Greek word ύλη (hyle), meaning "matter".[5] This was followed by methyl (Dumas and Peligot in 1834, meaning "spirit of wood"[6]) and amyl (Auguste Cahours in 1840[7]). The word alkyl was introduced by Johannes Wislicenus in or before 1882, based on the German word "Alkoholradicale" and then-common suffix -yl.[8][9]

See also

References

  1. ^ IUPAC, Compendium of Chemical Terminology, 2nd ed. (the "Gold Book") (1997). Online corrected version:  (2006–) "alkyl groups". doi:10.1351/goldbook.A00228
  2. ^ IUPAC, Compendium of Chemical Terminology, 2nd ed. (the "Gold Book") (1997). Online corrected version:  (2006–) "cycloalkyl groups". doi:10.1351/goldbook.C01498
  3. ^ Virtual Textbook of Organic Chemistry Naming Organic Compounds Archived 2016-05-21 at the Portuguese Web Archive
  4. ^ Mallavadhani UV, Sahoo L, Kumar KP, Murty US (2013). "Synthesis and antimicrobial screening of some novel chalcones and flavanones substituted with higher alkyl chains". Medicinal Chemistry Research. 23 (6): 2900–2908. doi:10.1007/s00044-013-0876-x.
  5. ^ Rocke, Alan (2012). From the Molecular World: A Nineteenth-Century Science Fantasy. Springer. p. 62. ISBN 978-3-642-27415-2. Ethyl radicals (named by Liebig in 1833 from the Greek and German word "aether" plus Greek "hyle"
  6. ^ Rocke, Alan (2012). From the Molecular World: A Nineteenth-Century Science Fantasy. Springer. p. 62. ISBN 978-3-642-27415-2. The methyl radical ... named from Greek roots, by Dumas and Peligot in 1834: methyl = methy + hyle ("spirit" + "wood")
  7. ^ Rocke, Alan (2012). From the Molecular World: A Nineteenth-Century Science Fantasy. Springer. p. 62. ISBN 978-3-642-27415-2. Amyl radicals ("amilène" was coined by Auguste Cahours in 1840, to designate a substance from potato starch after fermentation and distillation
  8. ^ Rocke, Alan (2012). From the Molecular World: A Nineteenth-Century Science Fantasy. Springer. p. 62. ISBN 978-3-642-27415-2. "Alkyl" was coined without fanfare by Johannes Wislicenus, professor at Würzburg; an early use (perhaps not the first) is in his 1882 article [22, 244]. The word was derived from the first three letters of "Alkoholradicale" combined with the suffix -yl; it was (and is) a generic term for any of those radicals who bear the "first names" methyl, ethyl, propyl, butyl, amyl, etc.
  9. ^ Wisclicenus, Johannes (1882). "Ueber die Schätzung von Haftenenergien der Halogene und des Natriums an organischen Resten". Ann. Chem. 212: 239–250. doi:10.1002/jlac.18822120107.
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