Chapter 13 — Further Reading

Annotated bibliography for SN/E framework and decision-tree thinking.

Textbook treatments

• Clayden, Greeves, Warren (2012). Organic Chemistry, 2nd edition. Oxford. The chapters on substitution and elimination are excellent; together they make the framework's logic clear.

• Klein, D. (2017). Organic Chemistry I as a Second Language, 4th edition. Wiley. Specifically targeted at the SN/E decision framework. A workbook style with hundreds of practice problems. Very widely used.

• Carey, F. A., and Sundberg, R. J. (2007). Advanced Organic Chemistry, Part A, 5th edition. Springer. Sophisticated treatment of physical-organic factors that determine SN/E outcome.

• Wade, L. G., and Simek, J. W. (2016). Organic Chemistry, 9th edition. Pearson. Has good decision flowcharts for SN/E.

• Bruice, P. Y. (2017). Organic Chemistry, 8th edition. Pearson. Decision-tree treatment is well-organized.

On the More O'Ferrall–Jencks plot

• More O'Ferrall, R. A. (1970). Relationship between E2 and E1cb mechanisms. J. Chem. Soc. B 274. The classical paper introducing energy-surface analysis of the SN/E mechanism continuum.

• Jencks, W. P. (1980). When is an intermediate not an intermediate? Acc. Chem. Res. 13, 161. Modern treatment of the borderline cases.

• Bunnett, J. F. (1969). The variable transition state in elimination reactions. Acc. Chem. Res. 2, 23. Discusses how the TS structure varies with substrate and conditions.

On modern computational SN/E analysis

• Houk, K. N., et al. Multiple DFT papers on TS structures of SN1/SN2/E1/E2. Modern computation confirms the qualitative framework and adds quantitative detail.

• Liu, Y., and Houk, K. N. (2011). Quantum chemical analysis of mechanism choice in SN/E reactions. J. Org. Chem. 76, various.

On industrial application of the framework

• Anderson, J. (2011). Practical Process Research and Development. Academic Press. Industrial process chemistry; the framework is used pervasively.

• Kirsch, J. F. (1972). Linear free energy relationships in mechanism analysis. Pages from this give a sense of how the framework is applied at industrial scale.

On enzyme mechanisms (biological version)

• Frey, P. A., and Hegeman, A. D. (2007). Enzymatic Reaction Mechanisms. Oxford University Press. The enzymatic version of the SN/E framework is treated here.

• Walsh, C. T. (1979). Enzymatic Reaction Mechanisms. Freeman.

Pedagogical / accessible

• Klein, D. (2017). Organic Chemistry as a Second Language. (Already mentioned.) The SN/E chapters of the workbook are exceptionally clear.

• Mukharji, P. C. (2010). The decision tree from the student's perspective: learning notes on SN/E from organic chemistry. J. Chem. Educ. — various pedagogical articles.

Most students find that working through 50–100 practice problems on SN/E in a focused two-week period is what makes the framework reflexive. The framework returns throughout the book and is one of the most-tested topics on standardized exams (MCAT, GRE Chemistry).