Sunday, February 28, 2010

Examples of Naming Cyclic Alkanes

Once again, I steal some problems from my textbook and do them here.
It's a ring made of six carbons, so it's a cyclohexane. Only one of the positions in the ring has any groups attached to it, and both groups are methyl groups, so it's 1,1-dimethylcyclohexane.
Another cyclohexane, obviously. This one has two groups at two different ring positions. The positions are across from each other in a 1,4 relationship. But which group gets numbered "1" and which one gets numbered "4"? Well, one is a methyl group and the other is a butyl group (four carbons in a straight chain). Alphabetical order determines which one comes first, so this is 1-butyl-4-methylcyclohexane.
The chain is bigger than the ring this time. So this compound is, as far as naming goes, defined as a five-carbon chain with a group attached at the first carbon, and the group that is attached is a cyclopropane ring. Therefore, we have 1-cyclopropylpentane.
The ring is a cyclopentane. Three groups this time, and all of them methyl groups, which makes naming this easy. Almost so easy that you could do it by yourself. But how do we number these groups? It doesn't matter which way we count, the smallest number we can start with is 1. This compound is 1,2,3-trimethylpentane.
This one is trickier. We definitely have a cyclohexane ring, but what are those groups attached to it. Well, let's start with the smaller one. It's an isopropyl group. See that? Probably not. Well, I told you, so now you know. Isopropyl group. The other one has four carbons. You might remember that there are four such groups possible. And if you have really been paying attention, it's clear that this is a sec-butyl group. Alphabetical order again, but the only prefix that matters for that is "iso-." That means the sec-butyl group is first. So this compound is 1-sec-butyl-2-isopropylcyclohexane.

Well, that's way that I learned to name this. And it's even the name that my solutions manual gives. But ChemSketch generated a different name that I am guessing is the true systematic name using proper IUPAC rules. The only difference is that the groups can't be written as isomeric forms of their straight-chain versions. This makes the nomenclature a bit messier (but it also scales up nicely, while the shortcut I'm using doesn't.

And that, children, is how to name cycloalkanes. I don't actually know what topic I'll cover next. You'll just have to wait to find out.

1 comment:

  1. the second to the last one, i think it should be 1,2,3-trimethylcyclopentane :)

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