Chapter 17 — Further Reading

Textbooks

• Clayden, Greeves, and Warren. Organic Chemistry, 2nd ed. (Oxford University Press, 2012). Chapter 24 ("Acyl substitution and elimination"; with alkyne content). The clearest treatment.

• McMurry, John. Organic Chemistry, 9th or later ed. (Cengage). Chapter 9 covers alkynes with mechanisms.

• Carey and Sundberg. Advanced Organic Chemistry, Part B: Reactions and Synthesis, 5th ed. (Springer, 2007). Sections on alkyne chemistry.

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

• Smith, J. G., and March, J. (multiple editions). Comprehensive treatment.

Primary literature: alkyne reactions

• Reppe, W. (multiple papers, 1928-1955). Reppe chemistry. Classic industrial alkyne reactions.

• Lindlar, H. (1952). The Lindlar catalyst. Helvetica Chimica Acta 35, 446-450.

• Brown, H. C., et al. (1973). Disiamylborane for alkyne hydroboration. Journal of the American Chemical Society.

Click chemistry

• Kolb, H. C., et al. (2001). "Click chemistry: diverse chemical function from a few good reactions." Angewandte Chemie 40(11), 2004-2021. The original click chemistry concept.

• Sharpless, K. B. (2022). Click chemistry Nobel Lecture. Angewandte Chemie 62(6).

• Bertozzi, C. (2022). Bioorthogonal click chemistry Nobel Lecture (joint Nobel with Sharpless and Meldal).

• Meldal, M. (2022). CuAAC Nobel Lecture.

Industrial alkyne chemistry

• Brand, K., and Dahmer, J. (2011). Industrial Applications of Acetylene Chemistry. Various reviews.

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

Sonogashira coupling

• Sonogashira, K., et al. (1975). Original Sonogashira coupling. Tetrahedron Letters 16(50), 4467-4470.

• Chinchilla, R., and Nájera, C. (2007). "The Sonogashira reaction: a booming methodology in synthetic organic chemistry." Chemical Reviews 107(3), 874-922.

Alkyne synthesis in natural products

• Diederich, F., et al. (2005). Acetylene Chemistry: Chemistry, Biology and Material Science. Wiley-VCH.

• Total synthesis literature (J. Am. Chem. Soc., Angew. Chem.): many syntheses use alkynes as alkene precursors.

Computational tools

• Avogadro (https://avogadro.cc/). Build alkynes; visualize the linear geometry.

• PubChem — look up: acetylene (CID 6326), 1-butyne (CID 7846), Lindlar catalyst.

Online resources

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

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

For practice problems

• Klein, David. Organic Chemistry as a Second Language, 4th ed. (Wiley). Chapter on alkyne chemistry.

• Karty, Joel. Organic Chemistry: Principles and Mechanisms, 2nd ed. (W. W. Norton, 2018). Chapter on alkyne chemistry.

• Sorrell, Thomas N. Organic Chemistry, 2nd ed. (University Science Books, 2006). Alkyne chemistry.

Mathematically inclined readers

• Streitwieser, A. (1961). MO theory of alkynes. Treatment of the linear C≡C π system.

Notes on this chapter's pedagogy

Chapter 17 is the alkyne complement to alkene chemistry (Ch 15-16). The unifying view: alkynes have two π bonds, so addition can happen twice; they have a uniquely acidic terminal C-H; and they are versatile precursors for cis or trans alkenes via selective reduction.

The chapter develops: 1. Structure and acidity (sp hybridization; pKa 25). 2. Addition reactions (similar to alkenes; can go twice). 3. Selective reduction (Lindlar → cis; Na/NH₃ → trans). 4. Alkynide nucleophiles (C-C bond formation). 5. Modern click chemistry (forward connection to bioconjugation).

Chapter 18 turns to radical reactions — a different mechanism for alkene/alkyne addition.