Orgo Complex Substituents Nomenclature Question

[BrazilianRider]

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Hey guys, I have a quick question that I just realized I never learned the answer to (in Chad's, and I don't remember from my Orgo I class since it's probably rarely tested on and irrelevant):

For a compound with a complex substituent and then a regular substituent, which substituent is written first?

For example, I know 1-bromo-2-chlorocyclohexane will be named in that order because the numbering will be the same either way and "B" comes before "C."

However, which would come first if they asked for the IUPAC of something like 1-tert-butyl-2-ionocyclohexane? In IUPAC it'd be 1-iono-2-(dimethylethyl)cyclohexane? Or 1-(dimethylethyl)-2-ionocyclohexane?

What if we were dealing with an isopropyl group? Would we alphabetize based on the "M" or the "P" in (2-methylpropyl)?

I honestly don't remember a question like this in Orgo I, but I'm sure if I had one it was covered on the very first exam and then never again!

Thanks in advance guys!

 

[FeralisExtremum]

When naming with a complex susbtituent, the numerical prefix/first letter DOES count, but that's the only situation where it should occur.

Example:

1-(1,2-dimethylpropyl)-3-ethylbenzene

Complex substituents aside, we ignore numerical prefixes and hyphenated prefixes (like di, tri, tert- and sec-) but not iso or cyclo.

 

[Daneosaurus]

When naming with a complex susbtituent, the numerical prefix/first letter DOES count, but that's the only situation where it should occur.

Example:

1-(1,2-dimethylpropyl)-3-ethylbenzene

Complex substituents aside, we ignore numerical prefixes and hyphenated prefixes (like di, tri, tert- and sec-) but not iso or cyclo.

Thanks, I wanted to help but did not understand the OPs Q

 

[Dotoday]

Iso and cyclo get alphabetized. Di, tri, tetra etc..... do not. T-butyl comes before iodo, because of B.
Odyssey, Kaplan, Dedtroyer and Schaums outlines have some good examples on that.

 

[youngy]

When naming with a complex susbtituent, the numerical prefix/first letter DOES count, but that's the only situation where it should occur.

Example:

1-(1,2-dimethylpropyl)-3-ethylbenzene

Complex substituents aside, we ignore numerical prefixes and hyphenated prefixes (like di, tri, tert- and sec-) but not iso or cyclo.

never knew that. Always thought di and tri didn't count, but i guess this is an exception