Linked Questions

0
votes
2answers
12k 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?
0
votes
1answer
1k 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 ...
2
votes
0answers
211 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 ...
0
votes
0answers
87 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 ...
0
votes
0answers
37 views

Hydration in Chloral [duplicate]

Chloral consists of two OH bonds on the same carbon, which is usually unstable, and leads to the evolution of a water molecule, and converts into an aldehyde. However, this is not observed in chloral, ...
0
votes
0answers
20 views

Existence of gem-diols [duplicate]

In the mechanism for Reimer-Tiemann's reaction, I was told that two alcohol substituents on the same carbon atom are unstable, and this is why salicylaldehyde is formed. In fact, this is not the first ...
13
votes
1answer
10k 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
2k 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 ...
5
votes
2answers
2k views

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
votes
1answer
373 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 ...
8
votes
2answers
855 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 ...