1
$\begingroup$

I'm a technical writer who is writing an instruction guide for a molecular modeling kit. I chose a compound based on my ability to construct two enantiomers from the kit in question, but I don't know what to call the compound or even which order to write the atoms in the formula. I tried ChemDoodle but by the time I figured out how to use the software to draw the molecule, I'd already exceeded my free structure-to-name limit.

The compound has a central chiral carbon with bonds to hydrogen, a hydroxide group, an amino group, and a chlorine. How do I write its formula? Is it CHClNH2OH? What order do I list the groups in, in other words? And what would I call it? I'm not sure what order to name the groups. Something like methanolchloramine? Any help is appreciated. I'll take the IUPAC name or any accepted name.

$\endgroup$
  • $\begingroup$ Do you also need to express the configuration of the enantiomers? $\endgroup$ – Loong Jan 1 '17 at 15:50
  • 2
    $\begingroup$ I think you should choose compound which wouldn't decompose immediately... $\endgroup$ – Mithoron Jan 1 '17 at 19:43
6
$\begingroup$

DHMO already gave the answer on how the compound as you drew it should be called. However, it has been commented that your compound is not stable and it also won’t be chiral for long. It will rapidly eliminate $\ce{HCl}$ to give a compound typically by retained name called formamide $\ce{HCONH2}$. Since formamide is planar, it is no longer chiral.

For the benifit of education, it would be better if you chose a compound that is sufficiently stable; whose isomers can be separated and ideally are sold separately.

$\endgroup$
  • $\begingroup$ As a plus point, the PIN is also 'formamide' (P-66.1.1.1.2.2). $\endgroup$ – orthocresol Jan 16 '18 at 22:01
4
$\begingroup$

The compound should be named aminochloromethanol.

You have correctly identified the parent hydrocarbon to be methane.

The substituents are $\ce{*Cl}$, $\ce{*NH2}$ (amine), and $\ce{*OH}$ (alcohol).

The order of precedence is:

  1. Cations
  2. Carboxylic acids
  3. Carboxylic acid derivatives
  4. Nitriles
  5. Aldehydes
  6. Ketones
  7. Alcohols
  8. Hydroperoxides
  9. Amines

Therefore, $\ce{*OH}$ (alcohol) goes to the suffix, while $\ce{*Cl}$ and $\ce{*NH2}$ (amine) go to the prefix.

The suffix for $\ce{*OH}$ is -ol.

The prefix for $\ce{*Cl}$ is chloro-.

The prefix for $\ce{*NH2}$ is amino-.

Since "amino-" comes before "chloro-" alphabetically, the combined prefix is aminochloro-.

Therefore, the name would be aminochloromethanol.

$\endgroup$
  • 8
    $\begingroup$ According to current IUPAC recommendations, a minimum of parentheses must be used around prefixes when no locants are necessary. Therefore, the correct name is amino(chloro)methanol. $\endgroup$ – Loong Jan 1 '17 at 14:09
  • $\begingroup$ @Loong 'Correct' as in preferred IUPAC name? $\endgroup$ – Martin - マーチン Feb 16 '17 at 9:12

Your Answer

By clicking “Post Your Answer”, you agree to our terms of service, privacy policy and cookie policy

Not the answer you're looking for? Browse other questions tagged or ask your own question.