Key Terms

• acetylide anion
• alkylation
• alkyne
• enol
• Lindlar Catalyst
• retrosynthetic
• tautomer

Summary of Reactions 9 • Summary of Reactions 9 • Summary of Reactions

No stereochemistry is implied unless specifically indicated with wedged, solid, and dashed lines.

• Preparation of alkynes
• Dehydrohalogenation of vicinal dihalides (Section 9.2)

• Alkylation of acetylide anions (Section 9.8)

• Reactions of alkynes
• Addition of HCl and HBr (Section 9.3)

• Addition of Cl2 and Br2 (Section 9.3)

• Hydration (Section 9.4)
• Mercuric sulfate catalyzed

• Hydroboration–oxidation

• Reduction (Section 9.5)
• Catalytic hydrogenation

• Lithium in liquid ammonia

• Conversion into acetylide anions (Section 9.7)