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Organic chemistry
Course: Organic chemistry > Unit 3
Lesson 1: Naming alkanes- Representing structures of organic molecules
- Naming simple alkanes
- Naming alkanes with alkyl groups
- Correction - 2-propylheptane should never be the name!
- Common and systematic naming: iso-, sec-, and tert- prefixes
- Naming alkanes with ethyl groups
- Alkane with isopropyl group
- Organic chemistry naming examples 2
- Organic chemistry naming examples 3
- Naming a cycloalkane
- Naming two isobutyl groups systematically
- Organic chemistry naming examples 4
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Organic chemistry naming examples 2
Organic chemistry naming examples involving branching and rings. Created by Sal Khan.
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- When do you use di and when bis?(15 votes)
- "Of the two kinds of numerical prefix (see Table 4.2), the simple di-, tri-, tetra-, etc. are generally recommended. The prefixes bis-, tris-, tetrakis-, etc. are to be used only with more complex expressions and to avoid ambiguity." From principles of nomenclature found at old dot IUPAC dot org. By complex, it does seem to mean that you can use them before things such as (1-methylethyl), but probably shouldn't in front of isopropyl.(14 votes)
- Why the name is not 2,2 bismethyl, 4,5 bis(1-methyl ethyl octane)? It was said that in case of systematic naming di is not used.(11 votes)
- Di- is used for simple groups like dimethyl and bis is used for complex groups like bis(1-methylethyl).(6 votes)
- Why not 4,5 di 1-methylethyl ?(3 votes)
- The rule for systematic naming is that simple branches use di-, tri- and tetra- as prefixes (dimethyl, tetranonyl, etc.) and that branches containing numbers use bis-, tris- and tetrakis- as prefixes (bis(1-methylethyl), tetrakis(1,2-dimethylcyclopentyl), etc.).(8 votes)
- Is there any convention for when we use a comma as opposed to a hyphen when naming these compounds? Sal, around, writes 2-2 instead of 2,2. Is there any difference between the two symbols? 04:25(2 votes)
- I think 2,2 is correct as opposed to 2-2.
You can see Sal corrects himself at. 6:37(4 votes)
- Okay,when ordering,Why not considering iso an ignored prefix just as before? can we say that di is stronger?(2 votes)
- Iso isn’t ignored. Di is.
i comes before m alphabetically which is why it’s isopropyl before dimethyl(4 votes)
- At. why does bis(1-methylethyl) come after 2,2 dimethyl? Arent we supposed to consier only the 'm' in dimethyl and 'e' in bid(1-methylethyl)? 8:35(3 votes)
- You consider the 'm' in bid(1-methylethyl), so methylethyl would go after methyl.(1 vote)
- at 9.55 , while writing the name of the compound in systematic form , we have changed, 4,5-di iso propyl to,4,5 bis (-methy ethyl).... but then y don't we change , 2,2-dimethyl to 2,2-bis methyl or something like that ... this is the only point bothering me.. kindly clarify my doubt ..(1 vote)
- We are locating the groups on the main chain. Each group needs a locating number (a locant).
The two methyl groups are on C2, so we say 2,2 dimethyl.
The isopropyl groups are on C4 and C5, so we say 4,5-diisopropyl.
If you are naming the isopropyl groups by their official name of 1-methylethyl, you must use the IUPAC rule, which state that the multiplying prefix for two of a complex group (a group with locant in the name), must be bis.
So, we say bis-(1-methylethyl).(4 votes)
- at, how come it is cyclopentyl not cyclopentane? 2:50(2 votes)
- Because it isn't the main group. If the 5-carbon ring wasn't attached to the cyclohexane then you are correct, it would be cyclopentane.
Ex., if you had a cyclopentane with a cyclobutane attached to the cyclopentane, it would be cyclobutyl cyclopentane.
Hopefully that clears it up, just comment if it doesn't.(2 votes)
- am kinda confused with sec and iso...
why you call it iso? plz help. thnx(1 vote)- The names "sec" and "iso" came before systematic names were invented. Here's an easy way to remember them.
"Iso" means "having a CH₃ group on the second-last carbon atom of the side-chain".
Isopropyl is CH₃CH(CH₃)-
Isobutyl is CH₃CH(CH₃)CH₂-
Isopentyl is CH₃CH(CH₃)CH₂CH₂-
Isohexyl is CH₃CH(CH₃)CH₂CH₂CH₂-, and so on.
"Sec" means "having a CH₃ group on the first carbon atom of the chain.
Sec-butyl is CH₃CH₂CH(CH₃)-
Sec-pentyl is CH₃CH₂CH₂CH(CH₃)-, and so on.
In practice, though, butyl is the largest group for which we use these "trivial" prefixes.(3 votes)
- Shouldn't the 2,2 dimethyl be 2,2 di-methyl (With the hyphen) 7:20(1 vote)
- Yes, I see what you mean. But, practically, it makes no difference.
You should use whatever you're meant to by your teacher or textbook.(2 votes)
Video transcript
I've pre-drawn some
molecules here. Let's see if we can use what
we know to name them. So what do we have? This first molecule right here,
I have a bunch of rings. This is a one, two, three, four,
five, six carbon ring. These are each four carbon
rings: one, two, three, four, one, two, three, four, so the
largest ring is essentially going to be our backbone. It's going to be this six-carbon
ring right here: one, two, three, four,
five, six carbons. That is a cyclohexane,
all double bonds. That's where we get the -ane,
six carbons hex-, it's in a cycle, cyclo-, and then
we have two of these four-carbon rings. So four carbons, we're dealing
with the prefix but-, but- for four. We've got two of them, so both
of these are butyl groups. But they're in a cycle,
so they're actually cyclobutyl groups. We have two things attached
to this ring right there. If we only had one thing
attached to it, you wouldn't have to number it. But when you have two
things, you start numbering at one of them. Let's say we start numbering
here, and you go in the direction so that the next group
has the lowest number. So in this case, you
want to go in the counterclockwise direction. If we went this way, it
would be one, two, three, four, five. This guy would be a five. If we go in the
counterclockwise, it would be one, two, three. This guy will only be a three. So this right here, we have
two cyclobutyls, so it's dicyclobutyl. We have two of them and
they are at the one and three positions. So at the one and three
position, I have two cyclobutyls on my cyclohexane
main ring. Let's try this one right here. I have a five-carbon ring, one,
two, three, four, five right there, and then I have a
one, two, three, four, five, six-carbon ring right there,
so this is going to be the main ring. That is a cyclohexane. It has six carbons on them in
a cycle, all single bonds. Attached to that, I
have a cyclopentyl group, -yl for the group. This is a cyclopentyl
group on it. We don't have to number it
because it's only one group attached to the main ring. If there was another group, we
would have to number it like we did up here. This is cyclopentyl. That's this part right here. Cyclopentyl attached
to cyclohexane: cyclopentylcyclohexane. Let's try this one over here. The first thing we want to do,
there's no cycles here, but we have to identify the
longest chain. To do that, let's just
count it out. It could be one, two, three,
four, five, six, seven. That's not the longest chain. Maybe it's one, two, three,
four, five, six, seven, eight. That looks like the longest
chain, so let's make that the longest chain. Let's make that the longest
chain right over there. We want to start numbering in
the direction so we encounter the first attached groups first.
We do want to start numbering down here, because we
have groups attached right on the two carbon. If we started over here, we'd
have to go pretty far until something's attached. So we go one, two, three,
four, five, six. seven. eight. We know we're dealing with an
octane, all single bonds. It's not a cyclooctane. It's not in a cycle,
so we know we're dealing with an octane. Now we just have to add
the groups to it. So what do we have here? This right here is
just one carbon attached to the main chain. This is another carbon attached
to the main chain. Both of these right here
are methyl groups. Meth- is for one carbon. Those are methyl groups. If you look at all of
them, these are the only methyl groups. These two up here aren't methyl
groups, so we have two methyl groups on our
entire chain, so it's going to be dimethyl. Both of the methyl groups our
at our two position, so this is going to be 2,2-dimethyl. This part right here is 2,2. That right there is
2,2-dimethyl. We're going to decide what order
to write it after we figure out what these are called
because it has to be in alphabetical order. This is 2,2-dimethyl. The whole chain is an octane. What are these over here? How many carbons do
we have here? One, two, three. They actually look the same. We have one, two, three here. We have one, two, three
there, so these are both propyl groups. If we deal with common names,
this is kind of that Y shape. You could call it sec-propyl
because this carbon right here that's attached to the main
chain is attached to two other carbons. But the more common one, because
it forms this Y shape, is isopropyl. We have two isopropyl groups. These are both isopropyl. We would have diisopropyl. They're occurring at the four
and five positions, two isopropyls at four and five. This is 4,5-diisopropyl. That's that group and that
group right there are accounted for with this. Now we have to just figure out
the order that we write it in. You ignore the di- or the tri-
out front and you just look at them in alphabetical order. We have an I for isopropyl. We have an M for methyl. Let's write the isopropyl first.
I've actually seen some people want to go for the p, but
the main thing I ignore is just the di- or the tri- in
front of the isopropyl. You shouldn't involve that. But everything after that,
you do involve. So I'll write the isopropyl
first. I comes before M, so this is going to be-- if we were
going to write the whole thing, this is going to be
4,5-diisopropyl, 2,2-dimethyl. Actually, this should
be a comma here. 4,5-diisopropyl-
2,2-dimethyloctane. And we're done. But this was just
the common name. You might remember that when we
deal with iso- or sec- or tert- butyl or propyl, that's
the common name. If we want the systematic name,
we can start at where we are attached to the main chain
and view that as one and then make the longest chain
with that as one. And so you could say that we
have a chain there and this would be both of these cases. So this is one, two carbons. Two carbons, we're dealing
with an ethyl. And on the first carbon, you
have a methyl attached to it. So you could also call each of
these groups a 1-methylethyl instead of an isopropyl. So you can either say isopropyl
for each of these groups or you could call each
of them a methylethyl if you do systematic naming. We have two of these
1-methylethyl groups, just like we had two isopropyl
groups. If you're using common naming,
you can say diisopropyl to say you have two of these groups. When you're using systematic
naming, you don't say di-1-methylethyl, although that
would probably would get the point across. You use bis-. Since we have two of them,
instead of writing di-, you write bis-. You write bis-(1-methylethyl)
That means you have two of these things right there, and
it's still in the four and the five position. If you look at it in
alphabetical order now, methylethyl comes after
methyl, right? So the order will now change. So now if you want to write it
with systematic naming, it would be written as
2,2-dimethyl. That's these two guys. 2,2-dimethylethyl, then you
would write this guy, so the order changed for the two
groups just based on how they're named. Bis-, and then over here you
have two 1-methylethyl groups. I know it's confusing, but when
you just break it down, it actually makes a reasonable
amount of sense. You have two of these
methylethyl groups. Oh, sorry, I forgot where
they're located. So we have them at the four and
five position, so in the four and five position,
we have two, so bis-(1methylethyl) groups. I know it's a little daunting
now, but it all makes sense when you break it down. And then we can just add
the octane at the end. Let me scroll over to the
right a little bit. Octane, and we're done.. Now this might seem more
confusing, but when you break it down, it makes sense. We have octane as
the backbone. We have two methyls. They're both sitting on
the two position. So you have two methyls sitting
on the two position, and then you have two
1-methylethyl groups sitting at the four and five
positions. So in the four and five
position, 1-methylethyl. You have an ethyl, and in the
one position you have a methyl, so that's
all it's saying. Or another way to think about
it, just in case this doesn't confuse you enough, you could
call it that, or you could say 4,5-diisopropyl. these two things are the same
thing: common naming, systematic. Hopefully, you found
that useful.