u/Daggers_and_shoes

IUPAC Parent Chain Help!

Hey all!

As per the current IUPAC Blue Book, I see that a parent chain must have the most amount of heteroatoms. However, that leads to confusion here:

OCCC(=O)O

The highest priority would be the carboxylic acid, so the chain would be CCCO? But this doesn't make sense, as I know the chain would be CCC.

I am struggling to understand the heteroatom priority. Below is the exact rule as per the Blue Book.

>In an acyclic compound consisting of individual atoms, alike or
different (an acyclic chain), the chain on which the nomenclature and
numbering is based is called the ‘principal chain’. When there is a
choice for the principal chain, the following criteria are applied, in
the order listed, until a decision is reached.

The principal chain:

(a) contains the greater number of heteroatoms of any kind;

(b) has the greater number of skeletal atoms;

(c) contains the greater number of the most senior acyclic heteroatom in
the following sequence: O > S > Se > Te > N > P > As
> Sb > Bi > Si > Ge > Sn > Pb > B > Al > Ga
> In >Tl.

Am I right in assuming all thats needed is to ensure that the hetero atom isn't terminal, i.e. is between 2 carbons?

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u/Daggers_and_shoes — 2 days ago

IUPAC Carbon double bond naming help!

Hey all!

I was recently wondering how one would go about naming C=C when the double bond isn't in the parent chain?

For example: CCCC(C=C)C(=O)O, i.e. a pentanoic acid with a an unsaturated ethyl group on carbon 2.

Thanks in advance!

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u/Daggers_and_shoes — 4 days ago