Conjugate bases negative charges

Neutral Lewis bases such as water alcohols and carboxylic acids are much weaker nucleophiles than their conjugate bases When comparing species that have the same nucleophilic atom a negatively charged nucleophile is more reactive than a neutral one... 

The conjugate base of a hydrocarbon is called a carbanion It is an anion in which the negative charge is borne by carbon Because it is derived from a very weak acid a car banion such as CH3 is an exceptionally strong base... 

The structure of the conjugate base is more like resonance structure B than A because the negative charge is on the more electronegative atom (O versus S). 

The two-step procedure includes formation of a N-substituted phthalimide 3, and its subsequent cleavage to the primary amine 5. Phthalimide (which can be obtained from reaction of phthalic acid with ammonia) shows NH-acidity, since the negative charge of the phthalimide anion (the conjugated base) is stabilized... 

The acidity of acetone and other compounds with C=0 bonds is due to the fact that the conjugate base resulting from loss of H+ is stabilized by resonance. In addition, one of the resonance forms stabilizes the negative charge by placing it on an electronegative oxygen atom. 

Electrostatic potential maps of the conjugate bases from methanol, acetic acid, and acetone are shown in Figure 2.4. As you might expect, all three show a substantial amount of negative charge (red) on oxygen. 

In what orbital do we find the negative charge for each conjugate base that we are comparing ... 

The ability to better stabilize the negative charge makes the acetate a weaker base than ethoxide (and hence its conjugate acid stronger than ethanol).. 

The overall negative charge of the H2P()4 species increases the attraction of its own conjugate base HP()42 to the departing proton. This creates a stronger bond, which indicates that it is a weaker acid. 

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