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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2Why are gem-diols unstable have you thought? Does the reason you have found imply that gem-diethers are unstable as well? – Pritt says Reinstate Monica Jun 16 '17 at 15:29
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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. – Kartikeya Badola Jun 16 '17 at 15:31
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4No, 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. – Ivan Neretin Jun 16 '17 at 15:32
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Okay then what exactly is happening? – Kartikeya Badola Jun 16 '17 at 15:33
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2https://chemistry.stackexchange.com/questions/10722/what-makes-c-o-more-stable-that-coh%e2%82%82 – Mithoron Jun 16 '17 at 15:49
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2Is 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. – logical x 2 Jun 17 '17 at 17:17