Starting with acetylene and ethylene oxide as the only sources of carbon atoms, show how to prepare these compounds. (a) S-Butyn-1-ol (b) S-Hexyn-1,6-diol (c) 1,6 -Hexanediol (d) \((Z)\)-3-Hexen-1,6-diol (e) \((E)-3\)-Hexen-1,6-diol (f) Hexanedial

Answer: (a) S-Butyn-1-ol: 1. Formation of 1-butyne by reacting acetylene with NaNH2 and adding another equivalent of acetylene. 2. Hydroboration-oxidation using 9-BBN and H2O2/NaOH. (b) S-Hexyn-1,6-diol: 1. Treat ethylene oxide with NaNH2 followed by the addition of acetylene to generate 1,6-hexadiyne. 2. Hydroboration-oxidation on both terminal alkynes using 9-BBN and H2O2/NaOH. (c) 1,6 -Hexanediol: 1. Synthesize S-Hexyn-1,6-diol as done in part (b). 2. Perform catalytic hydrogenation using H2 and Pd/C. (d) (Z)-3-Hexen-1,6-diol: 1. Synthesize 1,6-hexadiyne as done in part (b). 2. Perform Lindlar's catalytic hydrogenation on one terminal alkyne. 3. Hydroboration-oxidation using 9-BBN and H2O2/NaOH. (e) (E)-3-Hexen-1,6-diol: 1. Synthesize 1,6-hexadiyne as done in part (b). 2. Perform sodium or potassium in liquid ammonia reduction on one terminal alkyne. 3. Hydroboration-oxidation using 9-BBN and H2O2/NaOH. (f) Hexanedial: 1. Synthesize 1,6 - hexanediol as done in part (c). 2. Oxidation of both alcohol groups using NaIO4 or CrO3/H2SO4.