This is kind of like two questions but since they're related I have put them together.

Consider a monomer under a hopefully anatomically correct name 'Phenyl Carbolithia Divinylene Oxide [$\ce{C11H9LiO4}$] (For ease of understanding.)

Skeletal Formula for molecule PCDOAn image of the 3D structure

Would it be possible for me to find or estimate some basic properties (physical and chemical)? Or the 3D structure of the molecule (As opposed to the one I plotted, which is based on my estimation of dipole with minimal reasoning.)

By separating the molecules into parts:

  • Lithonate (Lithium Carbonate)
  • Benzene (Phenyl group)
  • Ethylene (Vinylene group)
  • Divinyl Ether

Perhaps now it is possible to make some predictions based on some functional groups? (Such as ether.)

Though theoretical chemistry has shown that such achievement in predicting a physical structure is unlikely, I am wondering if anyone would know specific properties of this molecule and the way they have deduced it in which I haven't consider.

The second part of the question may lead to the solution for the first part, by synthesizing such molecule.

My humble attempt at theorizing the chemical synthesis with my limited knowledge on the subject is based on condensation polymer. Perhaps having the separate parts of molecules mention previously dehydrated to form a chain, the molecule may be created if a similar polymer is formed except to have the carbon-oxygen backbone chain to form a ring instead.

I also have a slight inquiry on whether it is possible for the double bond to exist in this monomer; and whether my nomenclature for this substance is anatomically correct.

  • $\begingroup$ Sorry, but organic naming doesn't work like that - this compound should be named as substituted heterocyclic compound $\endgroup$
    – Mithoron
    May 16, 2015 at 22:38

2 Answers 2


I doubt that your "monomer" is very stable. Orthoesters, $\ce{R'-C(OR)3}$, are hydrolyzed under acidic conditions: $\ce{R'-C(OR)3 + 2 H+ -> R'-COOR + 2 ROH}$. The fate of your monomer is:


  • $\begingroup$ Could further explain what is it that makes the electron the oxygen group bonding to carbon instead of the sole oxygen atom as an ion? $\endgroup$
    – čaritisio
    May 17, 2015 at 23:42
  • $\begingroup$ @čaritisio When $\ce{RO-}$ leaves the molecule, a benzoate (ester of benzoic ester) is formed. Here, the $\ce{C=O}$ double bond is in conjugation with the $\pi$-system of the benzene. This is definitely lower in energy and I wouldn't be astonished if the formation of the ester would happen spontaneously. $\endgroup$ May 18, 2015 at 19:25

I agree with Klaus that your compound wouldn't be stable, although there could be some hope, if instead of lithium, you'd have alkyl group. Your compound is actually two molecules of ketene bound to lithium benzoate and even if you'd somehow create it, it would easily break down via mechanism starting with step presented in Klaus' answer. $\ce{RO-}$ is here enolate - good leaving group.


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