Chapter 9 Learning Objectives:

1. Be able to define:  alkyne, acetylide ion, enol, tautomerism, Lindlar's catalyst.
2. Be able to describe the structure of alkynes, including hybridization, bonds, and bond angles.
3. Be able to name a given alkyne, diyne, enyne, etc. using the IUPAC system of nomenclature.
4. Be able to draw the structure of an alkyne, diyne, enyne, etc. given the IUPAC name.
5. Be able to classify an alkyne as terminal or internal.
6. Know the methods for the preparation of alkynes from alkenes, including regents and intermediate compounds.
7. Know the acidity of terminal alkynes, conditions which will lead to the formation of acetylide ions, and the basicity of acetylide ions.
8. Know the reactivity of an acetylide ion, and the conditions under which it will act as a base or a nucleophile.
9. Be able to draw the mechanism for the formation of an acetylide ion and its subsequent reaction with an exchangeable hydrogen, a primary alkyl halide, an aldehyde or a ketone.
10. Be able to write the synthetic steps necessary to synthesize a target molecule given acetylene and other starting compounds.
11. Know the method for isomerizing an internal alkyne to a terminal alkyne.  Also be able to draw the mechanism for this transformation.
12. Know the method for isomerizing a terminal alkyne to an internal alkyne.  Also be able to draw the mechanism for this transformation.
13. Be able to predict the major product(s) (including regiochemistry and stereochemistry) for the following conditions:  HX, HX with H₂O₂, X₂, H₂O with H₂SO₄ and HgSO₄, hydroboration-oxidation, catalytic hydrogenation, diketone formation, oxidative cleavage.
14. Be able to draw the mechanism for the following addition reactions of alkynes:  HX, HX with H₂O₂, X₂, H₂O with H₂SO₄ and HgSO₄, hydroboration-oxidation, catalytic hydrogenation, diketone formation.
15. Be able to write the mechanism for acid-catalyzed keto-enol tautomersim.