Geminal diols or triols are very unstable and are easily converted into keto or carboxylic compounds. Triethyl orthoformate is a triether of similar structure. I want to know why the former is so unstable and the latter stable.

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    $\begingroup$ Why are gem-diols unstable have you thought? Does the reason you have found imply that gem-diethers are unstable as well? $\endgroup$ – Pritt says Reinstate Monica Jun 16 '17 at 15:29
  • $\begingroup$ Initially i thought that they are unstable because of stearic hindrance but when I first came across triethyl orthoformate i realised that this is not the case. $\endgroup$ – Kartikeya Badola Jun 16 '17 at 15:31
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    $\begingroup$ No, this has nothing to do with steric stuff. (You can have links to four C all right, and O is smaller than C.) Long story short, this is because H is labile and R is not. $\endgroup$ – Ivan Neretin Jun 16 '17 at 15:32
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    $\begingroup$ chemistry.stackexchange.com/questions/10722/… $\endgroup$ – Mithoron Jun 16 '17 at 15:49
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    $\begingroup$ Is this really a duplicate? This question asks for CH(OR)3 while the question in the link asks for CH(OH)3. I don't think this is a duplicate. $\endgroup$ – logical x 2 Jun 17 '17 at 17:17