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Chemistry Forums for Students => Organic Chemistry Forum => Topic started by: cseil on September 30, 2014, 12:56:44 PM

Title: Amide molecule name
Post by: cseil on September 30, 2014, 12:56:44 PM
O=C(C1CCC(C)CC1)N(CCCCC)CC(C)C

I'm starting with Organic Chemistry and the nomenclature. I just invented a structure, but the freeware version of ChemSketch doesn't tell me the name of molecules with more than 50 atoms, so I'm looking for a confirm.

It is a tertiary amine. It is bound to a pentane and to a 2-methylpropane.

So it is:
N-2-methylpropyl-N-pentyl-.

The first atom of the cycle is the one bound to the -COOH. So we have a 4-methylcyclohexane.
The name should be:

N-2-methylpropyl-N-pentyl-4-methylcyclohexanecarboxiamide.

Am I right?
I'm just interested into a hypothetic name.

PS. I'm italian, I don't really know if the order is different in some parts (for example butanoic anhydride is "anidride butanoica" in italian)
Title: Re: Amide molecule name
Post by: discodermolide on September 30, 2014, 01:11:00 PM
My ChemDraw says
N-isobutyl-4-methyl-N-pentylcyclohexanecarboxamide

Isobutyl and 2-methylpropyl and equally correct. Some of the trivial names are allowed by IUPAC.

Title: Re: Amide molecule name
Post by: cseil on September 30, 2014, 01:20:23 PM
Why
N-isobutyl-4-methyl-N-pentylcyclohexanecarboxamide
and not
N-isobutyl-N-pentyl-4-methylcyclohexanecarboxamide??
Title: Re: Amide molecule name
Post by: discodermolide on September 30, 2014, 01:45:10 PM
alphabetic order
Title: Re: Amide molecule name
Post by: AromaticAcrobatic on September 30, 2014, 11:29:18 PM
Cseil,
wheres the tertiary amine?
Also,
-COOH is a specific functional group, as far as I can see you don't have this functional group within your molecule.

I hope I'm not coming off like a dick, but if you can recognize these things now you'll have a much better time in a couple weeks/months..
 :D
Title: Re: Amide molecule name
Post by: cseil on October 01, 2014, 12:19:50 PM
That was my chain of thought, maybe it appeared a bit tricky  ;D
I was wrong with the -COOH of course, but I didn't consider it as a -COOH so it was just distraction.

I have an amide when a -COOH group has a -OH replaced by an amine, right?
Isn't that tertiary?

Where was I wrong?

Thank you for your answer. I really appreciate it  ;D
Title: Re: Amide molecule name
Post by: AromaticAcrobatic on October 01, 2014, 01:36:47 PM
Ok, well try and be a bit more careful. Carbonyls are molecules which have C=O, maybe this is the word you meant?
You are right about the Amide but generally you don't consider that a tertiary amine, its an amide. The reason being is a tertiary amine is going to have different properties then an amide, so you want to keep them separate.

 ;)