Acidity of alpha proton?

[m25]

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So if have a ketone with a methyl on one side and ethyl group on the other side, which alpha hydrogens are more acidic/more likely to be deprotonated such as in aldol condensation reaction?

 

[AwayFromReality]

I believe that has to do with the temperature of the reaction. If the temperature is low the less sterically hindered side will be deprotonated. In this case the methyl hydrogens will be more reactive. This will lead to what is known as the Kinectic product.

If the temperature of the reaction is high then the reaction will favor what is known as the thermodynamic product which is the most stable product. This depends on what reaction you are doing after you deprotonate the alpha hydrogen. Let's say we are doing an aldol condensation which forms an alkene. More substitued alkene is better so in this case the ethyl alpha hydrogen will be deprotonanted.