H-A Sinks Reacting with Common Sources

1 Lone Pair Sources Reacting with Acids 

Acids react by simple protonation of the electron source via proton transfer (see Section 3.6 for the calculation of the A eq). 

2 Bases Reacting with Acids Having an Adjacent CH 

This simple neutralization reaction always favors the weaker base. Thus the most acidic H is deprotonated, even if the acid has an adjacent CH. Because of the higher electronegativity of heteroatoms, protons on heteroatoms are usually lost before protons on carbon. The base n-butyllithium deprotonates the nitrogen of diisopropyl amine. The adjacent CH is about 14 orders of magnitude less acidic. Always check the eq to be sure your proton transfer is energetically reasonable. The Xgq for the reaction below is highly favorable, 10(50 - 36) = 10+14. 

3 Complex Metal Hydrides Reacting with Acids 

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Section 8.2 H-A Sinks Reacting With Common Sources... 

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