- You can recognize the following substituents on benzene as electron donors or electron acceptors via inductive and resonance effects:
Alkyl, amine, hydroxy/alkoxy, halogen, acyl, cyano, nitro, sulfonyl, CF3
Visualization: Sigma Complexes
- You can describe the role of electronegativity in controlling inductive effects.
- You can illustrate resonance effects for both electron donors and acceptors using proper resonance structures.
- Using all of the above information, you can classify each substituent as either activating or deactivating, and as either ortho/para or meta-directing based on use of resonance structures in the mechanism of electrophilic aromatic substitution.
- You can correctly apply all of these principles to predict the site of electrophilic aromatic substitution on a disubstituted benzene.
- You understand strategies for manipulating substituents to allow synthesis of any multiply-substituted benzene:
- Reduction of nitro to amine; oxidation of amine to nitro
- Reduction of acyl groups to alkyl groups
- Use of reversible sulfonation to achieve a particular directing effect
- The role of protection of amine and hydroxy substituents
- You can apply these principles to different aromatic systems (naphthalene).
Recommended end-of-chapter problems: 16-30, 16-32, 16-34, 16-35, 16-37, 16-39, 16-40, 16-42, 16-43, 16-45, 16-56, 16-57.
|