Chapter 17 Learning Objectives:

1. Be able to define:  activating  group, deactivating group, sulfonation, desulfonation, nitration, ortho-para director, meta-director, resonance stabilization, Friedel-Crafts acylation, Friedel-Crafts alkylation, Clemmensen reduction, Gatterman-Koch synthesis, benzyne mechanism, benzylic position.
2. Be able to explain why benzene does not undergo an electrophilic addition reaction with bromine.
3. Know the conditions, mechanisms (including all resonance structures), and be able to predict the products of a substituted benzene undergoing electrophilic aromatic substitution such as bromination, chlorination, nitration, iodination, phenol formation, sulfonation, desulfonation, Friedel-Crafts alkylation, and Friedel-Crafts acylation.
4. Be able to list the limitations to Friedel-Crafts alkylation reactions
5. Be able to classify a substituent as an ortho, para or meta director.
6. Be able to explain why a particular group is an ortho, para or meta director using mechanisms and words.
7. Be able to classify substituents as activating or deactivating and explain your prediction.
8. Know the conditions and be able to predict the products for the following reactions:  reduction of nitro group to amino group, synthesis of phenols from benzene sulfonic acids, reduction of ketones to methylene groups (CH₂) (Clemmensen Reduction), synthesis of benzaldehyde from benzene (Gatterrman-Koch reaction).
9. Know the conditions needed for the following reactions of alkyl substituents on aromatic rings: oxidation of the benzylic position, halogenation at the benzylic position.
10. Be able to write the synthetic steps necessary to synthesize a target molecule given benzene and/or other starting compounds.