Organic acid, water solubility ?

hello,

The rules of organic acids and organic solubility seems so sketchy compared to analytical chemistry.

CH3CH2NHCH3 vs Butanol vs H2C=CHCH2CH3 vs H2C=CHNHCH3

Why is the first one not the most acidic?

CH3CH2 N CH3 with a negative charge on N seems the most stable Hydrogen to give out of all the compound. Double bonds are more likely to try to take Hydrogen instead of give. Can't find any answers online or in the book that justifies this to be wrong.

Butanol vs CH3CH2OCH3 vs CH3CH2CH2OH vs OHCH2CH2OH
Solubility in H2O

Thanks!

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