Chemical Forums

Chemistry Forums for Students => Organic Chemistry Forum => Topic started by: JoeyBob on April 06, 2020, 09:26:01 PM

Title: Does LDA favor primary or secondary enolates and why?
Post by: JoeyBob on April 06, 2020, 09:26:01 PM

Like which??

Title: Re: Does LDA favor primary or secondary enolates and why?
Post by: OrganicDan96 on April 07, 2020, 06:30:14 AM

you need to show your working fist, what do you know about LDA?

Title: Re: Does LDA favor primary or secondary enolates and why?
Post by: JoeyBob on April 09, 2020, 06:55:33 PM

It favors less sterically hindered?

Title: Re: Does LDA favor primary or secondary enolates and why?
Post by: kriggy on April 10, 2020, 03:53:54 PM

Its dependant on reaction conditions.
In general, using LDA and low temperature favors kinetic enolate such as the one you drew. Using smaller base such as NaH and higher temperature favors the thermodynamic enolate. It can also be formed with bases such as triethylamine and a way how to trap the enolate such as silil protecting group or Bu₂BCl because in case of using weak base, the enolate is in equilibrium which favors the thermodynamic product