This question was bothering me

[Impulse155]

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On my dat I had this question

Let's say you have benzyl propanone. The ketone is on the benzyl carbon. Now let's say you taking tert butoxide with is. What hydrogen will it pull off.
If you react it with the alpha which is not very steric ally hindered on that side but you do have a benzene. But you make an alpha anion which has resonance on the ketone.

Then you have the bet carbon. Less serially hindered, the one t buo is preferred to go to. But no resonance.

Choice? Alpha or beta

 

[Cool Beans]

Alpha all the way! The pKa of the beta carbon (being alkane with no resonance) would be somewhere between 40-50 and that H isn't coming off.