The student should be able to:
- Introduction to Aromatics: Understand resonance for aromatics, bond angles and lengths, MO representations of aromatics, heats of hydrogenation of benzene and resonance energy of benzene and polycylic aromatics.)[11.1-11.8, 11.10]
- Nomenclature: Be able to name dienes. [10.5]. Given a structure write the IUPAC name, or given an IUPAC or common name draw the structure, for any substituted benzene. [11.7]
- Reactions: Carry out single-step
reactions using:
- Reactions of conjugated systems
- allylic halogenation [10.4]
- addition of hydrogen halides [10.10]
- addition of halogens [10.11]
- the Diels-Alder reaction [10.12-10.13]
- MO theory and cycloaddition reactions [10.14]
- Reduction of arenes
- catalytic hydrogenation [11.4]
- Birch reduction [11.11]
- Benzylic reactions
- free radical halogenation [11.12]
- oxidation of arenes [11.15]
- nucleophilic substitution [11.14]
- preparation of alkenylbenzenes [11.15]
- additions to alkenylbenzenes [11.16]
- Reactions of conjugated systems
- Mechanisms:
- * Write detailed mechanisms for reactions involving allylic and conjugated diene systems. [10.2-10.4, 10.10-10.12]
- * Classify cycloaddition reactions and predict whether they are allowed or forbidden using the frontier orbital model. [10.13-10.14]
- Hückel Theory: Determine
whether a p system is aromatic
or not. [11.18-11.20]
- Heterocyclic aromatic compounds [11.21-11.22]
- Concepts in Chapter 11: Introduction to Aromatics: Resonance for aromatics, bond angles and lengths, MO representations of aromatics, heats of hydrogenation of benzene and resonance energy of benzene.)[11.1-11.8, 11.10]
- Nomenclature: Given a structure write the IUPAC name, or given an IUPAC or common name draw the structure, for any substituted benzene. [11.9]
- Reactions: Carry out single-step reactions and multistep syntheses using combinations of single step reactions giving two, three four, etc,. steps.
- Mechanisms Write out detailed mechanisms for reactions involving electrophilic aromatic substitution. [12.2, 12.10-12.14] and organometallic reactions and alcohol oxidations.
- Reactions Carry out single-step
reactions and multi-step syntheses using:
- Electrophilic aromatic subtitution
- nitration [12.3]
- sulfonation [12.4]
- halogenation [12.5]
- Friedel-Crafts alkylation [12.6]
- Friedel-Crafts acylation [12.7]
- acylation-reduction [12.8]
- Clemmensen reduction
- Wolff-Kishner reduction
- Electrophilic aromatic subtitution
- Review objectives for Exams 2 and 3 and do problems similar to those from Exams 2 and 3. Many of the exam questions will focus on the reactions we have covered, their mechanisms and ways which they can be utilized in sysntheses. Other questions will be based upon principles, such as stereochemistry of structures and reactions, chirality, stereoisomers, stereoselective and stereospecific reactions and optical activity. The most important kinds of objectives are starred and the important questions from exams 2 and 3 and practice exams 2 and 3 are listed at the top or bottom of each of the exam pages.