Chapter 1 — Further Reading

A short list of resources that go beyond what this chapter covered, organized by what you might be interested in.

If you want a different textbook's perspective on the same ground

  • McMurry, J. (2023). Organic Chemistry, 10th edition. OpenStax. Free online. The best free functional-group-first alternative. McMurry's Chapter 1 covers much the same ground as ours but organizes it differently. Reading both perspectives can help you see what is essential to the subject (common to every treatment) vs. what is a presentation choice (different in every treatment).
  • Klein, D. (2020). Organic Chemistry, 4th edition. Wiley. The textbook most similar to this one in philosophy. Klein's skills-based approach is the direct intellectual ancestor of our mechanism-first approach. Not free, but widely available in university libraries.
  • Clayden, J., Greeves, N., and Warren, S. (2012). Organic Chemistry, 2nd edition. Oxford. The British-standard mechanism-first textbook, beloved by chemistry professors and sometimes forbidding to students. If you ever want the most elegant treatment of a topic that exists anywhere, Clayden is where you go. Heavy reading; some students find it enlightening, others find it intimidating. Worth sampling.

If you want more on the history

  • Brock, W. H. (1993). The Norton History of Chemistry. W.W. Norton. Excellent one-volume history of the whole field. The chapters on Berzelius and Wöhler are particularly good.
  • Le Couteur, P., and Burreson, J. (2004). Napoleon's Buttons: 17 Molecules That Changed History. Tarcher/Penguin. A popular, narrative treatment of a handful of influential molecules (aspirin, ascorbic acid, caffeine, nitric acid, etc.). Accessible, fun, and a nice antidote to the sterility of the subject as it sometimes appears in textbook form.
  • Djerassi, C. (1995). The Pill, Pygmy Chimps, and Degas' Horse. Basic Books. The autobiography of Carl Djerassi, who synthesized the first oral contraceptive. A look inside an organic chemist's working life.

If you want more on the thalidomide story

  • Stephens, T., and Brynner, R. (2001). Dark Remedy: The Impact of Thalidomide and Its Revival as a Vital Medicine. Perseus Publishing. The definitive popular treatment.
  • Ito, T., Ando, H., Suzuki, T., et al. (2010). Identification of a primary target of thalidomide teratogenicity. Science, 327(5971), 1345–1350. The paper that identified cereblon as the thalidomide target. Readable with some effort.
  • Chamberlain, P. P., and Hamann, L. G. (2019). Development of targeted protein degradation therapeutics. Nature Chemical Biology, 15(10), 937–944. Review of PROTACs, for after you have read some chemical biology.

If you want more on polyethylene and commodity chemistry

  • Young, R. J., and Lovell, P. A. (2011). Introduction to Polymers, 3rd edition. CRC Press. A standard textbook for polymer chemistry. Approachable as an upper-undergraduate resource.
  • Kim, H. (2018). The Chemistry of Polymers, 5th edition. RSC Publishing. Shorter than Young and Lovell; good for a quick orientation.

If you want to start using computational chemistry now

  • Avogadro project: https://avogadro.cc. Free, open-source, cross-platform. Read the documentation and do the getting-started tutorial.
  • WebMO: https://www.webmo.net. A web-based interface to several computational chemistry engines. Free version available for students; a fuller version often installed at universities.
  • PyMOL: https://pymol.org. Not strictly a computational-chemistry tool — it is a macromolecular-visualization tool — but indispensable if you ever want to look at a drug molecule bound inside its protein target. Free for educational use.
  • Jensen, F. (2017). Introduction to Computational Chemistry, 3rd edition. Wiley. The standard undergraduate textbook for the whole field. Come back to it after Chapter 2 of this book.

If you want to read primary literature

  • The Journal of Organic Chemistry (JOC), published by the American Chemical Society. Most articles are too specialized for a first-year student, but scanning the table of contents gives you a feel for what the current research questions are.
  • Organic Letters, also ACS. Short communications of new methods; more digestible than full JOC papers.
  • Angewandte Chemie (International Edition), published in Germany and Britain. High-impact. The "Highlights" feature, which summarizes recent work for non-specialists, is readable and worthwhile.
  • Chemical Reviews, ACS. Long, comprehensive reviews of mature subfields. If you ever want to know everything that has been published on a particular topic, start with a Chemical Reviews article.

If you want to know about organic chemistry as a profession

  • American Chemical Society (ACS), Division of Organic Chemistry. https://organicdivision.org. The professional society. Student memberships are inexpensive and include a subscription to Chemical & Engineering News, which gives you a window onto the field.
  • Chemistry jobs and careers, ACS. https://www.acs.org/careers.html. Guides to different chemistry careers, salary surveys, interview tips.
  • Graduate school is the path for most students who want to do research in organic chemistry. Appendix K of this book has a detailed discussion. The short version: a PhD in organic chemistry takes 5-6 years in the US, is tuition-free and stipend-supported at most universities, and opens up careers in pharma, materials, academia, and adjacent fields.

A reminder

You do not need to read any of this now. You do not need to read any of it ever to do well in this course. These pointers are here for the moments when something in this chapter catches your attention and you want to go deeper. If thalidomide fascinates you, read Stephens and Brynner. If polymers fascinate you, read Young and Lovell. If the history of vitalism fascinates you, read Brock.

But if the textbook is what you have time for, the textbook is what you have time for. That is enough.