Chapter 2 — Further Reading

For a deeper, more mathematical treatment of bonding

• Levine, I. N. (2014). Quantum Chemistry, 7th edition. Pearson. The standard graduate-level treatment. The first five chapters are within reach of a motivated undergraduate who has done a semester of physics.
• Pauling, L. (1960). The Nature of the Chemical Bond, 3rd edition. Cornell University Press. A classic. Pauling's exposition of hybridization and resonance set the conventions still used today. Written accessibly for the chemist without much mathematical apparatus.
• Albright, T. A., Burdett, J. K., and Whangbo, M.-H. (2013). Orbital Interactions in Chemistry, 2nd edition. Wiley. The standard intermediate reference between organic-chemistry-level treatments and full quantum chemistry. Valuable for understanding MO diagrams of more complex molecules.

For the same material in a different textbook

• McMurry, J. (2023). Organic Chemistry, 10th edition (OpenStax). Chapters 1 and 2. Functional-group-first organization; different emphasis, same core material.
• Klein, D. (2020). Organic Chemistry, 4th edition (Wiley). Chapters 1 and 2. Klein is especially good on skeletal-formula practice and on formal-charge identification by inspection.
• Clayden, Greeves, Warren. (2012). Organic Chemistry, 2nd edition (Oxford). Chapters 1–4. A beautiful exposition of bonding and orbitals, though at a higher mathematical level. Recommended only for students who want more depth.

For computational chemistry beginners

• Jensen, F. (2017). Introduction to Computational Chemistry, 3rd edition. Wiley. Chapters 1 through 3 cover Hartree-Fock and simple molecular-orbital calculations — the kind you can now do yourself in Avogadro or WebMO.
• Cramer, C. J. (2004). Essentials of Computational Chemistry, 2nd edition. Wiley. More accessible than Jensen; good first book.
• Foresman, J. B., and Frisch, A. (2015). Exploring Chemistry with Electronic Structure Methods, 3rd edition. Gaussian, Inc. The manual for Gaussian, one of the standard quantum chemistry packages. Approachable tutorial style.

For the allotropes-of-carbon case study

• Hirsch, A. (2010). The era of carbon allotropes. Nature Materials, 9(11), 868–871. Review of diamond, graphite, fullerenes, nanotubes, and graphene in a single article.
• Geim, A. K., and Novoselov, K. S. (2007). The rise of graphene. Nature Materials, 6(3), 183–191. A review by the Nobel laureates who isolated graphene.
• Novoselov, K. S., et al. (2005). Two-dimensional atomic crystals. Proceedings of the National Academy of Sciences, 102(30), 10451–10453. The short original paper — one of the most cited chemistry papers of the 21st century.

For morphine and alkaloid chemistry

• Robinson, R. (1925). A synthesis of tropinone. Journal of the Chemical Society, 762. Robinson's classic synthesis that led to the structural clarification of many alkaloids. Historical.
• Cordell, G. A. (2013). Fifty Years of Alkaloid Biology. Wiley. A broad survey.
• Gates, M., and Tschudi, G. (1956). The synthesis of morphine. Journal of the American Chemical Society, 78(7), 1380–1393. The first total synthesis of morphine — a milestone in organic chemistry history.

Tools to have at hand

• Avogadro (avogadro.cc). Molecule building and visualization. Used throughout this book.
• WebMO (webmo.net). Web-based interface to Gaussian, GAMESS, and other quantum-chemistry engines. Free educational version.
• PubChem (pubchem.ncbi.nlm.nih.gov). The NIH's database of chemicals. Look up any molecule by name; get its structure, properties, and spectra.
• ChemDraw (proprietary, ACS member discount). The industry-standard structure-drawing program. A free alternative is MarvinSketch from ChemAxon.

A reminder

Chapter 2 is a prerequisite chapter. The students who skip it, skim it, or rely on notes rather than practice will struggle for the rest of the book. The students who over-invest in it — who draw every homework structure by hand, who practice Lewis structures until they become automatic, who assign hybridization to every atom they see — make the rest of organic chemistry much easier.

If you have time, do more than the exercise set. Find a drug or natural product you are curious about. Look up its structure on PubChem. Go through it atom by atom: Lewis structure, formal charges, hybridization, polar bonds. Every molecule is a workout for these skills.