Chapter 16 — Further Reading

Textbooks

• Clayden, Greeves, and Warren. Organic Chemistry, 2nd ed. (Oxford University Press, 2012). Chapter 17 ("Electrophilic Addition") and Chapter 18 ("Other Alkene Reactions"). Comprehensive treatment.

• McMurry, John. Organic Chemistry, 9th or later ed. Chapters 7-8 on alkene reactions.

• Carey and Sundberg. Advanced Organic Chemistry, Part B: Reactions and Synthesis, 5th ed. (Springer, 2007). Chapters 4-5 on addition reactions and oxidation.

• March's Advanced Organic Chemistry, 7th ed. (Wiley, 2013). Chapter 15 covers alkene addition reactions in advanced detail.

Primary literature: hydroboration

• Brown, H. C. (1959). "Hydroboration: a powerful synthetic tool." Journal of the American Chemical Society 81, 4108. Brown's pioneering work on hydroboration.

• Brown, H. C. (1975). Organic Syntheses via Boranes. Wiley-Interscience. Brown's monograph; awarded Nobel 1979 (with Wittig).

• Brown, H. C., et al. (1984). 9-BBN and other selective boranes. Journal of the American Chemical Society.

Primary literature: oxymercuration

• Brown, H. C., and Sharma, K. T. (1968). Oxymercuration-demercuration. Journal of the American Chemical Society 90(13), 3349-3350.

Primary literature: dihydroxylation

• Sharpless, K. B., et al. (1976). Original dihydroxylation studies. Tetrahedron Letters.

• Sharpless, K. B. (1988). Asymmetric dihydroxylation. Journal of the American Chemical Society 110, 1968-1970.

• Kolb, H. C., et al. (1994). "Catalytic asymmetric dihydroxylation." Chemical Reviews 94(8), 2483-2547. Comprehensive review.

Primary literature: epoxidation

• Sharpless, K. B., and Katsuki, T. (1980). Asymmetric epoxidation of allylic alcohols. Journal of the American Chemical Society 102, 5974-5976.

• Jacobsen, E. N., et al. (1990). Mn-salen catalyst for asymmetric epoxidation. Journal of the American Chemical Society 112, 2801-2803.

Primary literature: ozonolysis

• Criegee, R. (1953). The mechanism of ozonolysis. Justus Liebigs Annalen der Chemie 583, 1-36. Foundational paper.

• Bailey, P. S. (1978). Ozonation in Organic Chemistry, Volume 1: Olefinic Compounds. Academic Press. Comprehensive ozonolysis reference.

Primary literature: hydrogenation

• Knowles, W. S. (2002). Asymmetric hydrogenation. Angewandte Chemie 41(12), 1998-2007. Knowles Nobel 2001.

• Noyori, R. (2002). Asymmetric hydrogenation. Angewandte Chemie 41(12), 2008-2022. Noyori Nobel 2001.

Industrial chemistry

• Weissermel, K., and Arpe, H.-J. (2003). Industrial Organic Chemistry, 4th ed. (Wiley-VCH). Industrial alkene chemistry.

• List, J., et al. (2008). "Trans fat in foods." Various reviews.

Computational tools

• Avogadro (https://avogadro.cc/). Visualize transition states for alkene additions.

• PubChem — look up: ozone (CID 24823), mCPBA (CID 6914), Hg(OAc)₂ (CID 16683034), 9-BBN (CID 21019099).

Online resources

• Master Organic Chemistry, "Alkene Addition Reactions" series. Free, undergraduate-level explanations.

• Khan Academy: Organic Chemistry — Alkenes. Free videos.

For practice problems

• Klein, David. Organic Chemistry as a Second Language, 4th ed. (Wiley). Chapter on alkene reactions. Excellent for solidifying patterns.

• Karty, Joel. Organic Chemistry: Principles and Mechanisms, 2nd ed. (W. W. Norton, 2018). Chapter on alkenes is well-organized.

• Sorrell, Thomas N. Organic Chemistry, 2nd ed. (University Science Books, 2006). Chapter on alkene reactions.

Notes on this chapter's pedagogy

Chapter 16 is the alkene "toolkit" chapter. It surveys the major alkene addition reactions, organized by what functional group they install. The key insight: each reagent has predictable regio- and stereo-chemistry that follows from its mechanism.

The pedagogical approach: 1. List the reagents and their products (the "menu"). 2. For each, explain mechanism and resulting selectivity. 3. Distinguish cation-mediated (rearrangement risk) from concerted (no rearrangement). 4. Highlight modern asymmetric methods. 5. Connect to industrial applications.

The chapter ends with case studies showing the reactions in action (margarine production; Taxol synthesis). Chapter 17 extends to alkynes; the chemistry is similar but with a triple bond.