Linked Questions

-1 votes
1 answer

Why enol is unstable? [duplicate]

Alkynes undergo acid-catalyzed addition of water across the triple bond in the presence of mercuric ion catalyst. The products are enol and keto. I want to know why is keto more stable than enol.
user24424's user avatar
16 votes
1 answer

Which factors determine the keto:enol ratio for aldehydes, ketones, and 1,3-dicarbonyl compounds?

Arrange the following compounds in order of increasing enol content: I think the order is D > C > B > A considering conjugation, hyperconjugation and hydrogen bonding. The enol formed in ...
Aditya Dev's user avatar
  • 7,676
15 votes
1 answer

Why is enol content higher in non-polar solvents?

Apparently, for keto-enol tautomerism, the enol content of a given carbonyl compound increases when in a non-polar solvent. What is the reason for this?
Pranjal Mittal's user avatar
4 votes
1 answer

Can vinyl alcohol react as a dienophile in Diels-Alder reactions?

For my organic chemistry exam I needed to synthesize cylcohexanone and in one of the steps a Diels-Alder reaction was required. I chose to use vinyl alcohol followed by an elimination reaction to get ...
JasonB's user avatar
  • 77
2 votes
2 answers

Why 3-chloroprop-1-en-1-ol is unstable?

In the treatment of HCl with acrolein 3-chloroprop-1-en-1-ol is the first product which is (my textbook says) unstable and turns into 3-chloropropanal. Why is this 3-chloroprop-1-en-1-ol unstable? is ...
Mockingbird's user avatar
  • 2,301
6 votes
1 answer

Dieckmann condensation's final protonation step

This is the Wikipedia image for the reaction mechanism: In the final protonation step, why does the enol tautomerize to the keto form? In the enol form the carbon-carbon double bond is in ...
pikachu's user avatar
  • 801
3 votes
2 answers

Compound having the highest enol content will be?

The answer written in book is 3 but no solution is given. After referring to some other question I think that hydrogen bonding can take place in compounds like 3 but am not sure about it. Am I right ...
Shresth Jain's user avatar
0 votes
0 answers

Which enol form is more stable?

I came across an example today while I was studying tautomerism. It is an example of tautomerism exhibited by acetylactone/1,3-diketone; given under the keto-enol systems under 1-3 migration/triad ...
Desai's user avatar
  • 451
0 votes
1 answer

Which of the following compounds possess more than one percent enol content? [closed]

Which of the following compounds possess more than one percent enol content? I understood that stability of enols are dependent on the hydrogen bonding in the compounds. But here, what is the ...
Bhawana Kanth's user avatar
3 votes
0 answers

Enol percentage comparison between 1,3 diketones and 1,2 cyclopentadione [closed]

To what extent does 1,2-cyclopentadione exist in enol form? Will it be more than for 1,3 diketones? 1,3-Diketone with active methylene groups can form hydrogen bonds with a 6-membered ring structure. ...
vanshita rawat's user avatar