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How would you name, if ethoxy ethane is disubstituted with hydroxy group on both alpha carbons? Here is it's formula,

$\ce{H3C-CH(OH)-O-CH(OH)-CH3}$

Is this compound stable at room temperature or not?

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    $\begingroup$ The site expects that you write explicit compact summary of your prior effort to answer the question, based on your knowledge and on searching for existing related info or answers. It would prevent others to tell you what you already know or what you could easily find yourself. $\endgroup$
    – Poutnik
    Jun 18 at 6:14
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    $\begingroup$ Not a stable species $\endgroup$
    – Waylander
    Jun 18 at 6:22
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    $\begingroup$ It looks like an ether of ethan-1,1-diol $\ce{CH3CH(OH)2}$ , which is the hydrated form of ethanal $\ce{CH3CHO}$. I don't think it is possible to make this ether, which could be called di(1-hydroxy)ethyl ether. $\endgroup$
    – Maurice
    Jun 18 at 8:57

1 Answer 1

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For the application of the nomenclature rules, it generally doesn't matter if the compound exists as long as it has consistent and well-understood bonding patterns and can be interpreted with a simple application of valence rules.

Using the usual straightforward nomenclature rules, you should see that the parent structure of the compound that is given in the question is ethanol. Using substitutive nomenclature, the complete name of the compound is 1-(1-hydroxyethoxy)ethan-1-ol.

In this case, however, a different rule is relevant. Since there are two identical parent structures (the two ethanol units), which are not alkanes, multiplicative nomenclature is preferred to substitutive nomenclature.

P-51.3.1 Preferred IUPAC multiplicative names
For a multiplicative name to be categorized as an IUPAC preferred name, certain restrictive conditions must be met. Multiplicative nomenclature is preferred to substitutive nomenclature for generating preferred IUPAC names to express multiple occurrences of identical parent structures, other than alkanes when

(1) the linking bonds (single or multiple) between the central substituent group of the multiplicative group and all subsequent structural units are identical and

(2) the multiplicative groups, other than the central multiplicative group, are symmetrically substituted; and

(3) the locants of all substituent groups on the identical parent structures, including suffix groups, are identical.

Therefore, the identical parent structures are expressed by the multiplicative name 1,1'-…di(ethan-1-ol).

The prefix oxy is now used for the multiplicative substituent group $\ce{{}-O-{}}$. So the complete multiplicative name is 1,1'-oxydi(ethan-1-ol).

1,1'-oxydi(ethan-1-ol)
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