OC Concept i didnt find in Chads Vid

[ammarm]

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I came across this concept while solving questions in destroyer (qsn 31). My question is as follows (please refer to the image): why are the protons in Ca more acidic than protons in Cb. Chad never explained that and i tried googling it but never came across a clear explanation. Can someone please share their knowledge about this? I would really appreciate your help. Thanks

 

[needzmoar]

When trying to estimate acidity, use the conjugate's stability as your guide. The resulting carbanion from Ca is primary. The resulting carbanion from Cb is secondary. What's more stable?

edit: The question asked for the most acidic proton? Are you sure it's not Cb ?

Enolates usually follow alkene stability, more substituted, more stable. If the problem stated that it was carried out at lower temperatures then I could see why it's Ca (kinetic product)

 

[ammarm]

When trying to estimate acidity, use the conjugate's stability as your guide. The resulting carbanion from Ca is primary. The resulting carbanion from Cb is secondary. What's more stable?

edit: The question asked for the most acidic proton? Are you sure it's not Cb ?

Enolates usually follow alkene stability, more substituted, more stable. If the problem stated that it was carried out at lower temperatures then I could see why it's Ca (kinetic product)

Thanks i actually got it and after thinking about it, Chad does go over it on Day 1 vidoes. Actually when proton is removed from Ca and Cb, a carbanion is formed. Based on stability of carbanion, primary is more stable than secondary which is more stable than tertiary. This is why the proton in Ca are more acidic because the resulting carbanion formed is a primary carbanion which is more stable than the secondary carbanion that would have formed when Cb was deprotonated by a base. Hope this helps!!

 

[AlbinoPolarBear]

When trying to estimate acidity, use the conjugate's stability as your guide. The resulting carbanion from Ca is primary. The resulting carbanion from Cb is secondary. What's more stable?

edit: The question asked for the most acidic proton? Are you sure it's not Cb ?

Enolates usually follow alkene stability, more substituted, more stable. If the problem stated that it was carried out at lower temperatures then I could see why it's Ca (kinetic product)

In this case, the kinetic product would be favoured by just the numbers. There are 3 Hydrogens at Ca, while there are only 2 Hydrogens at Cb.

 

[ammarm]

im not quite understanding the thermodynamic vs kinetic product? do you mind briefing it out for me