2008 Final exam review

2008 Final exam review - theexam ,andafewshortminor...

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Below is a comprehensive list of topics that you need to familiarize yourself with for the exam. The exam will have one major spectroscopy question, and a few short minor spectroscopy questions. There are a few supply reagent/product questions. Also there may be a some multistep synthesis questions. Unavoidably, the exam will have some multiple choice questions to cover some of the earlier topics (like ‘which molecule containing a carbocation is the most stable, which is the strongest acid, etc.). Approximately 50% of the exam will revisit topics from problem sets I assigned (not the book problems) and exams 1-4 from this semester. You are allowed one 5x7 signed reaction card for the exam (both sides covered with reactions and/or reagents). This will be turned in with the exam. Here is a modified syllabus and associated notes on the reactions and concepts you are responsible for. Part I. The Structure of Organic Compounds Introduction and organic nomenclature 1.1, 2.1, 2.2, 2.4, 2.5, 2.7, 2.9 Bonding in organic compounds 1.2-1.9 Drawing formulas Lewis Dot structures Identifying functional groups Atomic and Molecular Orbital Theory Hybridized orbital geometries (sp,sp2, sp3) Sigma, pi, sigma*, pi* relationships Drawing resonance structures, energies from resonance structures Alkanes, alkenes, alkynes & conformational analysis 2.3, 4.1-4.5 Newman projections, dihedral relationships and energy diagrams Bonding differences between alkenes and alkynes Highly substituted alkenes are more stable than less substituted alkenes Cycloalkanes & conformational analysis 7.1-7.6 Energy and ring size (cyclopropane, butane, pentane, hexane) Strain, idealized bond angles and strain, torsional strain Conformations of 3,4,5,6 membered rings and associated energy diagrams Preferred conformations of rings and substituent effects (which is most stable conformation) Stereochemistry 6.1-6.11 (6.12) Representing stereochemistry in structures (dashs, wedges)(R/S; E/Z assignments; Cahn- Ingold Prelog assignments)
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enantiomers, diastereomers, meso achiral compounds, chirality/achirality converting 2D into 3D w/ Fisher projections Part II. Reactivity of Organic Compounds Organic Reaction Classes 5.2 Addition to alkenes, alkynes: 4.6, 4.7 Carbocations and stability (trityl and benzylic>allylic>3>2>1) Carbocation migration via hydrogen or methyl shifts Hydration with aqueous acid (Mark substitution) Oxymercuration/Demercuration (Mark substitution, NaBH4 demercuration)
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