[movies]

Maybe we need an "IUPAC Nomenclature for Dummies" book

I agree, but who would write it if no one understands the jargon in the first place!

[janne18]

If you've ever tried to read the IUPAC guidlines on the IUPAC website then you're probably even more confused than when you started.  I've gone there looking for answers to a specific naming question and given up after an hour of futile searching.

I agree, it's a little difficult to find what you are looking for in IUPAC's guidelines. But I think I found the right rule.
Quote: "61.3 - In accordance with the principle (a) of Part .2 of this rule, hydrocarbons containing several chains attached to one cyclic nucleus are generally named as derivatives of the cyclic compound; and compounds containing several side chains and/or cyclic radicals attached to one chain are named as derivatives of the acyclic compound." http://www.acdlabs.com/iupac/nomenclature/79/r79_83.htm

According to this, I think the compound should be named after the alifatic chain. Why ChemDraw doesn't arrive to the same conclusion I'm not sure.
I also think it's easier to interpret 2-bromo-3-methyl-5-phenylheptane than 1-(6-bromo-5-methylheptan-3-yl)benzene. But that is my personal view.

[movies]

hydrocarbons containing several chains attached to one cyclic nucleus are generally named as derivatives of the cyclic compound

I think that the coumpound in question should fall under this clause, so it would make sense that it's named as a benzene derivative.  Anyone else have an opinion?

[corey2]

just stick to the simplest name possible, every chemist in the world do this, and this is also the reason for the use of common names.
Major evidence is the natural compound name system: just say menthol and not 5-Isopropyl-2-methyl-cyclohexanol

[dexangeles]

just stick to the simplest name possible, every chemist in the world do this, and this is also the reason for the use of common names.
Major evidence is the natural compound name system: just say menthol and not 5-Isopropyl-2-methyl-cyclohexanol

yes but memorization of all common names is hard, plus not all compounds have common names.

[corey2]

true, but hen you have learned the major principal families of compounds, when you reach to a compound that you don't know you name it by comparison.
Remember also that very common structures don't follow IUPAC standard atom numeration, and that's much harder than remebering names.

[janne18]

I think that the coumpound in question should fall under this clause, so it would make sense that it's named as a benzene derivative.  Anyone else have an opinion?

Except for the reason that the compound doesn't contain several chains attached to the phenylgroup. The compound has only one chain attached to the ring.

[movies]

Except for the reason that the compound doesn't contain several chains attached to the phenylgroup. The compound has only one chain attached to the ring.

I see.  I had interpreted it differently.  I think that you are right.

[Winga]

How about this one?

[jdurg]

Hmmm.  Not being an o-chemist this can be tough for me, but I've come up with 4-phenyl-2,3,5,6-methylheptane.

[janne18]

Hmmm.  Not being an o-chemist this can be tough for me, but I've come up with 4-phenyl-2,3,5,6-methylheptane.

I would have "tetra" before methyl. So 4-phenyl-2,3,5,6-tetramethylheptane or 2,3,5,6-tetramethyl-4-phenylheptane, but I'm not sure if phenyl should come before or after tetramethyl. Anyone remember?

[Winga]

Methyl comes first according to alphabetic order.
"Tetra-" is only a prefix.

[dexangeles]

agree with winga  

[jdurg]

Since I'm not an organic chemist, I say that as long as I can determine the structure from the name, then the name is correct.