Why Does Polymerisation Occur in Diols?

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Discussion Overview

The discussion revolves around the polymerization of diols, specifically focusing on the mechanisms and conditions under which they polymerize with themselves. The scope includes theoretical aspects of polymer chemistry and the behavior of different types of diols.

Discussion Character

  • Exploratory, Technical explanation, Debate/contested

Main Points Raised

  • One participant inquires about the polymerization of geminal diols, represented as HO-R-OH, where R is an alkyl group.
  • Another participant emphasizes the importance of the number of carbons in the alkyl group, suggesting that only simple cases of diols on the same carbon readily polymerize to poly acetals.
  • A participant describes the conditions under which poly ethers can be formed from vicinal diols and discusses the complexity of resulting mixtures when longer alkyl chains are involved.
  • One participant notes that geminal diols exhibit different behaviors compared to other diols, indicating a distinction in their polymerization characteristics.

Areas of Agreement / Disagreement

Participants express differing views on the polymerization behavior of geminal versus vicinal diols, indicating that the discussion remains unresolved with multiple competing perspectives.

Contextual Notes

Limitations include the dependence on the specific structure of the alkyl group and the conditions under which polymerization occurs, which are not fully explored in the discussion.

jsmith613
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why does
HO-R-OH
(where R is an alkyl group) polymerise?
i.e: with itself?
 
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How many carbons in that "alkyl" group?
 
chemisttree said:
How many carbons in that "alkyl" group?

This extremely important, since only the simplest case of the diols existing on the same carbon are readily polymerized to poly acetals (geminal diol). The simplest is polyformaldehyde, a white powder that is poorly soluble in water with reaction to depolymerize to a formaldehyde solution.

One can envision under acidic conditions and with removal of H2O to drive the reaction, that poly ethers can be made for other alkyls of longer than one methylene (vicinal diols and greater intervening methylenes). For the shorter alkyls, (2,3,4, and 5 intervening methylenes), dimers, trimers, and the monomer can cyclize and remove intermediates (volatile under the conditions of reaction heat and H2O removal) needed to make longer polymers so complex mixtures result.
 
Last edited:
That's why I asked the question. Geminal diols behave very differently than other diols.
 

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