Course Details

The broad learning goals in this class are listed below by chapter. The goals are framed somewhat as questions. Success in having mastered a learning goal is measured in terms of the student’s ability to respond thoughtfully to these questions. Of course, the answers must reflect an understanding of the structure and reactivity of organic molecules and the theory of ground and transition state governing factors. The questions are intended to be framed within the context of the chapter material. Specific and detailed learning goals for each chapter are extensive and are beyond the scope of this Overview.

Chapter 1: What is organic chemistry?
Do you recall the key ideas from General Chemistry, such as electronic structure models of bonding (Lewis dot structures, valence bond theory, resonance, molecular orbital theory), thermodynamics, kinetics, and acid/base theory? What are the important trends of Periodic Table? What are organic compounds? Is color a molecular property? Can you draw and identify phenol, benzene, aniline, pyridine, and thiophene?

Chapter 2: Organic structures
What are hydrocarbon frameworks? What are functional groups? How to draw organic molecules? How to classify carbon atoms by oxidation level? How to name compounds? What do chemists really call compounds? What is meant by the skeleton of an organic molecule? What are the common abbreviations of groups, reagents, solvents, conditions, and other shorthand notation used by organic chemists? How to draw easily understood molecules? What is meant by a natural product? What is meant by a synthetic compound? What are primary metabolites? What are secondary metabolites?

Chapter 3: Determining organic structures
What is X-ray crystallography? What is mass spectrometry? What is carbon nuclear magnetic resonance spectroscopy? What is proton NMR spectroscopy? What is infrared spectroscopy? How to infer structural information from spectroscopic data?

Chapter 4: Structure of molecules
What is the Aufbau principle? How do we know that electrons have different energies? How do electrons ‘fill’ atomic orbitals? How do atomic orbitals combine to make molecular orbitals? What is the linear combination of atomic orbitals theory? Why do organic molecules adopt linear, planar, tetrahedral, and more complex structures? What is hybridization? What is the connection between shape and electronic structure? How to draw the shapes and depict the energetics of molecular orbitals in simple molecules in simple ways? How to predict ‘locations’ of lone pairs and empty orbitals?

Chapter 5: Organic Reactions
Why don't molecules typically react with one another? Why do molecules sometimes react with one another? How does molecular shape and structure determine reactivity? Do chemical reactions involve electrons moving from full to empty orbitals? How to depict chemical reactions? How to identify nucleophiles and electrophiles? How to represent the movement of electrons using curly arrows?

Chapter 6: Nucleophilic addition to the carbonyl group
How and why does the carbonyl group react with nucleophiles? How to explain the reactivity of the carbonyl group using molecular orbital theory and curly arrow convention? What sorts of molecules can be made by the reaction of nucleophiles with carbonyl groups? How does acid or base improve/accelerate reactions of the carbonyl group?

Chapter 7: Delocalization and Conjugation
What are the interactions between orbitals over many bonds? How does stabilization by sharing
electrons over more than 2 atoms work? Where does color of organic compounds come from? How does molecular shape and structure determine reactivity? What is the structure of aromatic compounds? What does the term aromatic mean?

Chapter 8: Acidity, basicity, and pKa
Why are some molecules acidic and other molecules basic? Why are some acids strong and other acids weak? Why are some bases strong and other bases weak? How to estimate acidity and basicity using pH and pKa? How are structure and equilibria impacted in proton transfer reactions? Which protons in a complex molecule are acidic? Which protons in a complex molecule are most acidic? Least acidic? Which lone pairs in a complex molecule are basic? Which lone pairs in a complex molecule are least basic? Most basic? How do acid and base ideas affect reactivity and solubility? What quantitative descriptions of acids and bases can be used to understand reactivity? Solubility? Medicine design?

Chapter 9: Using organometallic reagents to make C-C bonds
What is an organometallic reagent? Are organometallic reagents nucleophilic? Basic? Acidic? How does electronegativity and polarization impact bonding? What is a Grignard reagent what are organolithium reagents? How are organometallic reagents made from halogenated compounds? How are organometallic reagents made by deprotonation of carbon atoms? How are organometallic reagents used to make new carbon-carbon bonds from carbonyl containing compounds?

Chapter 10: Nucleophilic substitution at the carbonyl group
What is nucleophilic attack followed by loss of a leaving group at a carbonyl compound? What makes a good nucleophile? What makes a good leaving group? What is a tetrahedral intermediate and why is it relevant? How to make acid derivatives? What is the reactivity of an acid derivative? How to make ketones from acids? How to reduce acids to alcohols?

Chapter 11: Nucleophilic substitution at C=O with loss of oxygen
What is meant by replacement of a carbonyl oxygen? What is acetal formation? What is imine formation? What is the stability of imines? What is the Strecker reaction what is the Wittig reaction? How do we draw reaction mechanisms for reactions at carbonyl oxygens that occur with loss of the carbonyl oxygen?

Chapter 12: Equilibria, rates, and mechanisms
What controls equilibria processes? What is free energy enthalpy and entropy? What determines reaction rate? What are intermediates? What are transition states? How does catalysis with acid or hydroxide work? What are the effects of temperature on reaction rates and equilibria? What effect does solvent have on rate and equilibria? What is a rate equation and how does it relate to the reaction mechanism?

Chapter 13: 1H-NMR: Proton nuclear magnetic resonance
What is proton NMR and how to interpret NMR spectra? What is the difference between proton NMR and carbon NMR? What is proton-proton coupling? What is proton integration? What is chemical shift? How to use NMR spectroscopy to determine the structure of an unknown molecule?

Chapter 14: Stereochemistry
What is meant by the 3-dimensional shape of molecules? What is the mirror image of a molecule? What is the symmetry of a molecule? How are mirror image molecules separated? What are diastereomers? What are epimers? How does shape govern biological activity? How to present stereochemical information as part of a drawing of an organic molecule? How can chemical reactions give mirror image products?

Chapter 15: Nucleophilic substitution at saturated carbon
What is nucleophilic attack on a saturated carbon atom? What are the products? How does substitution at the saturated carbon atom differ from attack at a carbonyl containing compound? How to draw the two mechanisms of nucleophilic substitution? How to draw and describe the intermediates and transition states in substitution reactions? How does substitution influence stereochemistry in nucleophilic addition reactions? What sort of nucleophiles can substitute and what sort of leaving groups can be substituted in nucleophilic substitution reactions? What sorts of molecules can be made from substitution reactions and what can they be made from?

Chapter 16: Conformational analysis
What is meant by three-dimensional shape of molecules? What is meant by conformation? What effect does a molecule shape have on its reactivity? What are the energetic profiles of single bond rotations? What is the low energy conformation of a rotomer? What is a transition structure in a rotomer? Are saturated organic compounds flat molecules? What are the conformations of 6 membered rings? What is a chair structure? What is a boat structure? What is a twist boat structure? What are the differences in the energies between the possible conformations of 6 membered rings? How to draw 6 membered ring compounds accurately? How does ground state conformation effects bear on transition structures?