Chapter 9, Problem 9.34SP

Show how you would accomplish the following synthetic transformations. Show all intermediates.

1. a. 2,2 — dibromobutane → but — 1 — yne
2. b. 2,2 — dibromobutane → but — 2 — yne
3. c. but — 1 — yne → oct — 3 — yne
4. d. trans — hex — 2 — ene → hex — 2 — yne
5. e. 2,2 — dibromohexane → hex — 1 — yne
6. f. cyclodecyne → cis — cyclodecene
7. g. cyclodecyne → trans — cyclodecene
8. h. hex — 1 — yne → hexan — 2 — one, CH₃COCH₂CH₂CH₂CH₃
9. i. hex — 1 — yne → hexanal, CH₃(CH₂)4CHO
10. j. trans — hex — 2 — ene → cis — hex — 2 — ene