[Ciubba]

the preceding compound should have a methyl group on carbon 2 if you number from the left or 5 if you number from the right, but I couldn't figure out how to do that with SMILES.

Should it be named 3-bromo-5-methylhexane or 4-bromo-2-methylhexane? My professor insists on the former, but my book says the latter.

[Borek]

Is that what you mean? Then the SMILES is

CC(C)C(Br)CC

Note that

C(C)CC(Br)CC

actually doesn't differ from

CCCC(Br)CC

as what you did you added another carbon to the first one in the chain (effectively making the chain longer). You need this additional carbon after the 2^nd carbon in the chain, then it is a branch, not an extension.

[Ciubba]

Yes, that's exactly what I meant to draw. So, which naming scheme is preferred? I'm using the 7th edition of Organic Chemistry by Paula Bruice, if that helps.

[cseil]

Yes, that's exactly what I meant to draw. So, which naming scheme is preferred? I'm using the 7th edition of Organic Chemistry by Paula Bruice, if that helps.

I would call it: 3-bromo-2-methyl-pentane.

It's 3-bromo-2-methylpentane or 3-bromo-4-methylpentane: I think your book says to call the molecule with the first lower number possible. So in this case the first number is 3 in both cases, the second number is 2 or 4 so you choose 2.

PS. You can use chemicalize.org when you're not certain about a name.

[Ciubba]

Sorry, I just realize that the picture is missing a carbon. It should be



However, the link you posted agrees with me and the book in naming the compound (4-bromo-2-methylhexane). I guess I'll have to talk my professor on Monday.