[Edher]

Hello,

        I'm having trouble drawing the structure of the following organic molecule, could you please verify my attempt?

2-butyl 3-aminopentanoate

Thanks,
Edher

[AWK]

There are at least 3 errors in your formula (1-butyl, pentavalent carbon, tetravalent nitrogen)

CH3-CH2-CH(NH2)CH2-COO-CH(CH3)CH2CH3

[lemonoman]

I stewed about this question for almost an hour

I was hesitant to accept AWK's structure, I'm like, "You can't call that a 2-butyl".  You have to call it sec-butyl or 1-methylpropyl.  But to my chagrin, and whether IUPAC accepts it or not (it probably does), let it be known throughout the land that you can call that a 2-butyl group.

http://www.nysaes.cornell.edu/pheronet/cpds/2rbuz714oate.html shows you...and shows that there is a stereogenic center.

Everyone have a nice night...I should have been in bed an hour ago lol

Edit: 1-methylpropyl, not 1-methylpentyl - thanks AWK

[AWK]

I stewed about this question for almost an hour

I was hesitant to accept AWK's structure, I'm like, "You can't call that a 2-butyl".  You have to call it sec-butyl or 1-methylpentyl. 

You mean 1-methylpropyl, don't you.

I did not discuss name correctness, just I showed correct linear structure for this non-IUPAC name.

[lemonoman]

1-methylpropyl, yeah.  My mistake.  I changed it.

And I wasn't ragging on your answer...just mentioning in passing that I'd never heard of this nomenclature.  I learned something.

[victor]

I got this picture from my chemistry drawing software...

[AWK]

There is a big difference between 2-butyl 3-aminopentanoate and 2-butyl-3-aminopentanoate

[victor]

what's the difference then??I see that both of the name have the same letters except one letter is coloured red...

[AWK]

space ' " means that this is an ester, "-" means butyl is joined to aminopentanoate skeleton

[victor]

ahh..yes, thanks for the details..I wasn't pay attention on that..
these are the structures according to the drawer..

[AWK]

Drawer can do what you recommend it to do. It assumes you know a chemical nomenclature

[plu]

"You can't call that a 2-butyl".  You have to call it sec-butyl or 1-methylpropyl.
Edit: 1-methylpropyl, not 1-methylpentyl - thanks AWK

Quote: "One recent development in substitutive
nomenclature is to place locants immediately before the part of the name
(suffix, infix, prefix or descriptor) that they qualify. The CNOC (Commission on
Nomenclature of Organic Chemistry) Guide also recommends that the
traditional names of alkyl groups be supplemented by alkanyl names that are
derived by adding the suffix -yl to the name of the parent hydrocarbon, rather
than replacing the ending -ane by the suffix -yl, as in current practice. For
example, we can write three names for (CH3)2CH- : isopropyl, 1-methylethyl
and propan-2-yl. The last systematic name is short, easy to understand and to
use and fully able to cope with further substitution. The substituted group
(ClCH2)2CH- can be named 2-chloro-1-(chloromethyl)ethyl or, in the new
form, 1,3-dichloropropan-2-yl. This last name is shorter and quite appealing."

[lemonoman]

"One recent development in substitutive
nomenclature is to place locants immediately before the part of the name
(suffix, infix, prefix or descriptor) that they qualify. The CNOC (Commission on
Nomenclature of Organic Chemistry) Guide also recommends that the
traditional names of alkyl groups be supplemented by alkanyl names that are
derived by adding the suffix -yl to the name of the parent hydrocarbon, rather
than replacing the ending -ane by the suffix -yl, as in current practice. For
example, we can write three names for (CH3)2CH- : isopropyl, 1-methylethyl
and propan-2-yl. The last systematic name is short, easy to understand and to
use and fully able to cope with further substitution. The substituted group
(ClCH2)2CH- can be named 2-chloro-1-(chloromethyl)ethyl or, in the new
form, 1,3-dichloropropan-2-yl. This last name is shorter and quite appealing."

That's interesting...where did you find that?