Acid Base problems can be easy and complicated if you don't know the general rules to them. They've appeared on previous test (including the practice final) and I thought it'd be helpful to do a problem for review.
This problem is taking from Sapling Chapter 2, Question #3.
The first thing you must consider is carbon hybridization. Remember, the sp carbons are more electronegative than sp3 carbons. The carbons that are electronegative are more acidic.
Alkanes< Alkene<Amine<Alkyne<Water
If you remember that the stronger the acid, the weaker its conjugate base, you won't miss another acid-base problem. The equilibrium arrow will always point in the direction AWAY FROM the strongest acid OR TOWARDS the conjugate base of the strongest acid.
Initially, I got this wrong a few times until I figured out exactly why I was messing up. I could never remember what direction to draw the arrow. I remember from these simple words: Arrow points away from the strongest." Hopefully this can help someone!
Reference: http://www.saplinglearning.com

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