Advices For Studying Organic Chemistry

Acetate anion Ethoxide anion
(Weaker base) (Stronger base)

3. The electrostatic potential maps for the acetate and the ethoxide ions:

Figure 3.9 Calculated electrostatic potential maps for acetate anion and ethoxide
anion. Although both molecules carry the same –1 net charge, acetate
stabilizes the charge better by dispersing it over both oxygens.

1) The negative charge in acetate anion is evenly distributed over the two oxygens.

2) The negative charge is localized on its oxygen in ethoxide anion.

3) The ability to better stabilize the negative charge makes the acetate a weaker

base than ethoxide (and hence its conjugate acid stronger than ethanol)..

3.10C INDUCTIVE EFFECTS OF OTHER GROUPS

1. Acetic acid and chloroacetic acid:

CO

O

H 3 C CO

O

< < CH 2

<

< <

<

H Cl< < H