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Topic: nomenclature confirming  (Read 17794 times)

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Ice-cream

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nomenclature confirming
« on: May 04, 2005, 06:17:35 AM »
hey can anyone confirm whether i've got the name of this organic compound right?

CH3CH(Br)CH(CH3)CH2CH(phenyl)CH2CH3

is it 2-bromo-3-methyl-5-phenylheptane? (or is it 6-bromo-5-methyl-3-phenylheptane?)

Offline ATMyller

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Re:nomenclature confirming
« Reply #1 on: May 04, 2005, 09:09:20 AM »
I wouldn't consider the benzene ring as a substituent. In that case it would be (4-bromo-1-ethyl-3-methylpentyl)benzene.
Chemists do it periodically on table.

Ice-cream

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Re:nomenclature confirming
« Reply #2 on: May 04, 2005, 10:02:04 AM »
but there are 7 carbons in the longest chain...so wouldn't it be a phenyl, coz if it was only 1 or 2 carbons, it would be benzene...is that right?

Offline Winga

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Re:nomenclature confirming
« Reply #3 on: May 04, 2005, 12:16:30 PM »
Benzene should be act as a substituent when the longest cabon chain is more than 6 carbons.
« Last Edit: May 04, 2005, 11:13:27 PM by Winga »

786mine

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Re:nomenclature confirming
« Reply #4 on: May 08, 2005, 05:18:55 AM »
(2S,3R)2-Bromo-3-methyl-5-phenylheptane

--

forgot to add the R and S
« Last Edit: May 09, 2005, 04:11:01 PM by 786mine »

janne18

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Re:nomenclature confirming
« Reply #5 on: May 09, 2005, 03:00:31 PM »
Benzene should be act as a substituent when the longest cabon chain is more than 6 carbons.

Not nessisary right. A hydrocarbon containing a small ring attached to a long chain is normaly named after the chain and vice versa. But there are some exceptions.
ex:
phenyl-CH2-phenyl  named diphenylmethane
phenyl-(CH2)5-phenyl named 1,5-diphenylpentane

The reason for this is that chains containing several side chains or  cyclic radicals are named as derivates of the acyclic chain.

786mine

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Re:nomenclature confirming
« Reply #6 on: May 09, 2005, 04:13:01 PM »
Benzene should be act as a substituent when the longest cabon chain is more than 6 carbons.

I disagree, if the chain has 6 carbons and so does benzene, but there are a few other branches on the 6 carbon chain, it is easier to make the 6-carbon chain as your root and the benzene ring as one of the branches.

Offline sapta

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Re:nomenclature confirming
« Reply #7 on: May 10, 2005, 12:00:04 PM »
It would be 2-Bromo-3-methyl-5-phenylheptane not  because of number of C atoms(it's insignificant here) but because of the presence of Br(which has to be taken as functional group here) in the aliphatic chain.Another example-

    C6H5.CH2.CHBr.CHBr.CH2.CH3  would be 2,3-Dibromo-1-phenylpentane.

I AM NOT QUITE SURE ABOUT ALL THESE. PLZ CORRECT ME IF IAM WRONG.      

janne18

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Re:nomenclature confirming
« Reply #8 on: May 12, 2005, 03:40:31 PM »
(2S,3R)2-Bromo-3-methyl-5-phenylheptane

--

forgot to add the R and S

I don't think it's possible to say anything about the stereochemistry in this case. So you can't use (2S,3R) in yhe name.

786mine

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Re:nomenclature confirming
« Reply #9 on: May 12, 2005, 05:19:50 PM »
I don't think it's possible to say anything about the stereochemistry in this case. So you can't use (2S,3R) in yhe name.

True, but it does form a stero center, so you have to put either R or S. Depending on how you want to name it.

corey2

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Re:nomenclature confirming
« Reply #10 on: May 12, 2005, 07:30:21 PM »
2-bromo-3-methyl-5-phenylheptane is correct considering it an halifatic compound with substituents, but it is also correct (according to IUPAC) (4-Bromo-1-ethyl-3-methyl-pentyl)-benzene considering it an aromatic compound. It's really normal that organic molecules have different names.

6-bromo-5-methyl-3-phenylheptane is wrong because the coefficients are bigger.

Offline movies

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Re:nomenclature confirming
« Reply #11 on: May 12, 2005, 10:39:05 PM »
True, but it does form a stero center, so you have to put either R or S. Depending on how you want to name it.

There are three stereocenters in the molecule, by the way.  You can't make any assumptions about the stereochemistry from how it is drawn, so typically no R or S labels are added at all.  Perhaps you intend to say that the compound is racemic,  however, it is not necessarily racemic since there is the possibility of diastereomers.

dexangeles

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Re:nomenclature confirming
« Reply #12 on: May 13, 2005, 03:08:38 AM »
this is the problem with IUPAC Nomenclature that I've noticed....too many possible naming, why don't we just stick to 1 and get it done with, let's even rid of the common names

Offline movies

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Re:nomenclature confirming
« Reply #13 on: May 13, 2005, 11:58:23 AM »
this is the problem with IUPAC Nomenclature that I've noticed....too many possible naming, why don't we just stick to 1 and get it done with, let's even rid of the common names

I think common names are definitely on the way out, but old habits die hard.  When in doubt, I go with the name that AutoNom generates through ChemDraw.  For this compound, it suggests that the name should be 1-(6-bromo-5-methylheptan-3-yl)benzene.  I can't tell you how it arrives at that name, but it presumably follows the IUPAC naming conventions.

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.

dexangeles

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Re:nomenclature confirming
« Reply #14 on: May 13, 2005, 12:02:46 PM »
Maybe we need an "IUPAC Nomenclature for Dummies" book

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