This has to do with acidity and basicity. I have to determine which is more acid

Question

This has to do with acidity and basicity. I have to determine which is more acidic (or more basic) and explain why.

1. Between TMS-acetylene and methane, choose the more acidic (or basic) and explain why?
- I believe the trimethylsilylacetylene is more acidic due to the location of the alpha hydrogen and being more readily deprotonated while all of the hydrogens in methane are equal and makes it harder to deprotonate one of the alpha carbons. Am I correct or is there more to this?

2. Between sodium hydroxide and sodium acetate, which is the stronger base (or acid) and why?
- I KNOW that sodium hydroxide is a stronger base but I don't know why...any ideas?

3. Between Pentane-2,4-dione vs 3,3-dimethylpentane-2,4-dione, which is more acidic/basic?
- I'm not sure if these are bases or acids let alone know which is more basic/acidic.

Explanation / Answer

1)TMS-acetylene is more acidic, in addition to your explanation, in acetylene carbon has sp hybridisation so % of s-character is more by which carbon gets more electronegativity so that it can withdraw electron pair towards itself hence protons can be easily left so it's more acidic

2)NaOH is stronger base than sodiumacetate because CH3COONa is basic salt & is made of weak acid CH3COOH+NaOH, hence a salt of basic nature can be obtained

3)pentane-2,4-dione is more acidic because 3-carbon containing hydrogens can be removed by both carbonyl groups and the same is not possible in 3,3-dimethylpentane2,4-dione because 3-carbon doesn't contain hydrogens

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