Linked Questions

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9k views

Why are geminal diols unstable? [duplicate]

The most stable of: (a) $\ce{(CH3)2C(OH)2}$ (b) $\ce{CH3 C Cl (OH)2}$ (c) $\ce{CH3CN}$ is $\ce{CH3CN}$, because the other two are geminal diols. How can we tell that geminal diols are unstable?
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1answer
683 views

Instability of gem dihydroxy compounds [duplicate]

Organic compounds containing two hydroxy groups on one carbon (gem dihydroxy) are unstable and tend to lose water molecule. However, Boron, sulfur and phosphorus with two OH groups are stable. What is ...
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0answers
240 views

Why is ninhydrin stable as a geminal diol? [duplicate]

The following image depicts the structure of ninhydrin - $\ce{C9H6O4}$ Ninhydrin, as you see has two hydroxyl group attached to same carbon. In general, geminal diol (or gem-diol, for short) are ...
2
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0answers
118 views

Why are organic ortho acids unstable? [duplicate]

Ortho acids like orthoformic acid (methanetriol, $\ce{HC(OH)3}$), orthocarbonic acid ($\ce{C(OH)4}$), and orthoacetic acid (ethane-1,1,1-triol, $\ce{H3C\bond{-}C(OH)3}$) are known to be unstable and ...
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0answers
80 views

Why is triethyl orthoformate stable? [duplicate]

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 ...
12
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1answer
7k views

Formation of a stable hydrate

Question: Which of the following does not form a stable hydrate? I think they mean nucleophilic addition of water. For compound (C), on reaction with water, the product formed is The product has ...
7
votes
2answers
957 views

Why does formaldehyde exist primarily as the gem-diol in aqueous solution?

From Wikipedia, Methanediol is the product of the hydration of formaldehyde $\ce{H2C=O}$, and predominates in water solution: the equilibrium constant being about $10^3$ and in a 5% by weight ...
6
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2answers
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Does intramolecular hydrogen bonding occur with carbonic acid and geminal diols?

Is an intramolecular hydrogen bond possible in such compounds? What are the requisites to have intramolecular hydrogen bonding?
4
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1answer
286 views

Are gem-diols on alkenes stable?

Geminal diols are unstable, except for a few exceptions like chloral hydrate. I wish to ask if a gem-diol alkene is also stable. Their structure: suggests to me that the intramolecular hydrogen bond ...
7
votes
2answers
625 views

What is the driving force for imine formation?

I know this that when a primary amine is reacted with a carbonyl compound, an imine is formed: I'm wondering why the position of this equilibrium lies to the product side / right-hand side. Why is ...