Question

3) Show how hex-1-yne might be converted to: a. 1-bromohex-1-ene b. 1,1,2,2-tetrabromohexane C. 2-bromohex-1-ene d. 2-bromohexane e. 2,2-dibromohexane 4) For each compound, give the product(s) expected from (1) HgSo./H2SO4-catalyzed hydration and (2) hydroboration-oxidation. a. hex-1-yne b. hex-2-yne c. hex-3-yne d. cyclodecyne 5) Predict the product(s) you would expect from treatment of each compound with (1) dilute, neutral KMnO, and (2) warm, basic KMnO, then dilute acid. a. hex-1-yne b. hex-2-yne c. hex-3-yne d. 2-methylhex-3-yne e. But-1-ene → butan-2-ol 6) Show how you might synthesize the following compounds, using acetylene and any suitable alkyl halides as your starting materials. If the compound given cannot be synthesized by this method, explain why. a. hex-1-yne b. hex-2-yne c. hex-3-yne d. 4-methylhex-2-yne e. 5-methylhex-2-yne

Answer 1

solution: ③ Hex-f-you (ter) + HBY 4202 Anti. Markownikov's rul 1- bromo hex-fene Brz (exess) Dcm Br Br 1,1, 22 telrabromu hetune (104) & H Br Marko Aika unikov's rule Br 2 - Bromo-hex-trene pd, cacos, pbcoala HBr Lindlar catalyst Br 2 Bromo hetune HBr. HBr Br Br Br 2,2 dibromo hexare