OC Alkyne Rxn (tautomerization)

[NavyDDS1990]

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So, I'm working on alkyne reactions in OC.

I was just wondering how you guys figure out when reaction goes through Tautomerization.

Does this happen only with specific reagents? such as H2SO4 and other reagents?

Thank you!

 

[SmileDesignersDDS]

It happens when something is stable in two conformations. It doesn't really happen with a specific reagent. Like if you have something like an enol which is not really stable it will go to the keto form. Honestly that's the only tautomerization I have ever seen

 

[NavyDDS1990]

It happens when something is stable in two conformations. It doesn't really happen with a specific reagent. Like if you have something like an enol which is not really stable it will go to the keto form. Honestly that's the only tautomerization I have ever seen

so enol would be something with OH and an alkene right next to it right?

 

[SmileDesignersDDS]

 

[emitpeels]

Basically whenever you have a double bond next to a C bonded to an OH it will tautomerize.

 

[StumpMT]

^What he said. Here are two examples from Chad.

 

[Dotoday]

Usually enols are less stable than ketones. Therefore enols will tautomerize to ketones or aldehydes. When you are doing Alkynes hydration, you are making enols, therefore you will see a tautomeric shift. Hope this helps. Good luck.

 

[NavyDDS1990]

thanks guys 🙂