3 Handout (Estimating basicity)

3 Handout (Estimating basicity) - How to identify the more...

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How to identify the more basic molecule or more basic site in a molecule Introduction: Bases are molecules that can accept a proton (H + ). The basic sites in a molecule are lone pairs. These can be lone pairs on neutral (uncharged) atoms, which are not often shown. Or they can be lone lairs on anionic (negatively charged) atoms, which are much easier to identify. Most molecules have multiple basic sites (types of lone pairs). However, when acting as bases, only the most basic site will participate in the acid- base reaction. Therefore, it is important to be able to identify the most basic lone pair in a molecule. How to: There are three basic methods of trying to estimate the basicity of a lone pair. 1) The more stable base is the less basic. (This works well for anionic bases) 2) The base which is more willing to share its lone pair is the more basic. (This works well for neutral bases) 3) The base with the less acidic conjugate acid is more basic. (This works well for ones that we can guesstimate the acidity of using the table from class or the table below). Base
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3 Handout (Estimating basicity) - How to identify the more...

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