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Topic: IUPAC nomenclature problem  (Read 5306 times)

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Offline shalikadm

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IUPAC nomenclature problem
« on: June 04, 2012, 04:18:58 AM »
I'm using a software called MarvinSketch 5.9.4 to check my nomenclature answers...It seems accurate..But I found something that I cant understand.Here is the structure I inserted and got 2-ethenyl-formylpentanamide but I think it must be 2-formyl-2-propylbut-3-enamide...
1.parent hydrocarbon chain must have maximum number of double bonds..
2.then  :rarrow:the maximum number of C atoms

EDIT:now seems to be not much accurate getting this,

my suggestion : 4-bromo-3-propylpent-4-en-1-ol
« Last Edit: June 04, 2012, 04:42:16 AM by shalikadm »

Offline discodermolide

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Re: IUPAC nomenclature problem
« Reply #1 on: June 04, 2012, 05:12:48 AM »
I'm using a software called MarvinSketch 5.9.4 to check my nomenclature answers...It seems accurate..But I found something that I cant understand.Here is the structure I inserted and got 2-ethenyl-formylpentanamide but I think it must be 2-formyl-2-propylbut-3-enamide...
1.parent hydrocarbon chain must have maximum number of double bonds..
2.then  :rarrow:the maximum number of C atoms

EDIT:now seems to be not much accurate getting this,

my suggestion : 4-bromo-3-propylpent-4-en-1-ol

Here are the names as produced by ChemDraw. Good luck!
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Offline shalikadm

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Re: IUPAC nomenclature problem
« Reply #2 on: June 04, 2012, 05:23:44 AM »
sorry..who is corect then ?....me or marvinsketch or chemdraw ?

Offline discodermolide

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Re: IUPAC nomenclature problem
« Reply #3 on: June 04, 2012, 05:27:51 AM »
sorry..who is corect then ?....me or marvinsketch or chemdraw ?

I'd put my money on ChemDraw although others here may disagree.
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Offline shalikadm

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Re: IUPAC nomenclature problem
« Reply #4 on: June 04, 2012, 05:32:33 AM »
sorry..who is corect then ?....me or marvinsketch or chemdraw ?

I'd put my money on ChemDraw although others here may disagree.

so there are others who disagree with ChemDraw's nomenclature ?

Offline shalikadm

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Re: IUPAC nomenclature problem
« Reply #5 on: June 04, 2012, 05:40:40 AM »
I'm eager to know the correct one ! ;)
here's another one....

my guess : methyl 6-bromo-3-propylpent-3-enoate
« Last Edit: June 04, 2012, 05:52:23 AM by shalikadm »

Offline shalikadm

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Re: IUPAC nomenclature problem
« Reply #6 on: June 04, 2012, 06:03:39 AM »
I think mervinsketch is not obeying rules...I found that it selects the longest C chain without thinking about double or triple bonds..am I correct ?

Offline discodermolide

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Re: IUPAC nomenclature problem
« Reply #7 on: June 04, 2012, 06:17:43 AM »
I'm eager to know the correct one ! ;)
here's another one....

my guess : methyl 6-bromo-3-propylpent-3-enoate

You did not specify the geometry of the double bond. here is a picture of what I think you meant.
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Offline shalikadm

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Re: IUPAC nomenclature problem
« Reply #8 on: June 04, 2012, 07:00:48 AM »
I have no understanding about that spiral thing..
any way this structure was taken from a book and it was printed as,

There was nothing describing the geometry.

Offline sjb

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Re: IUPAC nomenclature problem
« Reply #9 on: June 04, 2012, 07:39:57 AM »
I have no understanding about that spiral thing..
any way this structure was taken from a book and it was printed as,

There was nothing describing the geometry.

"That spiral thing" is just a means of showing undefined double bond geometry. I wouldn't want to guess if the structure you have shown is cis or trans.

Offline orgopete

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Re: IUPAC nomenclature problem
« Reply #10 on: June 04, 2012, 05:27:01 PM »
sorry..who is corect then ?....me or marvinsketch or chemdraw ?

The Marvinsketch and ChemDraw names are the same, so I would go with them. The difference is ChemDraw uses the common variants of substituents, vinyl rather than ethenyl or t-butyl rather than 1,1-dimethylethyl.
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