15.12 Extra Problems
6. Draw the following compounds. a) 2-ethoxypentane
b) 1,2-epoxybutane
c) 3-ethylfuran
d) THF (tetrahydrofuran) e) cis-3-ethyl-1,2-epoxycyclopentane
f) m-propoxyphenol
g) ethylthiohexane
h) ethyl hexyl sulfide i) cyclohexene oxide
j) 2-butyl-1-propylsulfide
k) 3-methoxyhexane
l) 2,3-dimethylthiophene
m) ethyl ether
7. Name the following compounds.
8. Show the best method for preparing the following ethers via the Williamson ether synthesis. You must start with alcohols or phenols as the organic reactants. a) ethoxycyclohexane
b) tert-butyl methyl ether
c) propoxybenzene
d) ethoxypropane
9. Use alkoxymercuration-demercuration to make the following ethers from an appropriate alkene and alcohol. a) ethoxycyclopentane
b) 2-methoxyhexane
c) 1-methyl-1-propoxycyclohexane
10. Explain why alkoxymercuration-demercuration is not a good method to make 1-ethoxyheptane.
11. Determine the necessary reagents needed to perform the following reactions. a) 1-pentene to 1,2-epoxypentane
b) ethyl ether to ethyl bromide c) cyclopentene to trans-cyclopentane-1,2-diol
d) propyl bromide to ethyl propyl sulfide e) butane to 1-chlorobutan-2-ol
f) phenol to ethyl phenyl ether
g) pentene to 2-ethoxypentane
12. Show the best method for preparing propoxybenzene via the Williamson ether synthesis.
13. Show the best method for preparing tert-butyl propyl sulfide from a thiol and alkyl bromide.
14. Show the mechanism for the following reaction.
15. Show the mechanism for the following reaction.
16. The following spectra are of a compound with the formula C4H10O.
17. Provide the major organic product in the following reactions.
18. Draw the missing reactants for the following reactions.
19. Show the mechanism for the following reaction.
20. Show the mechanism for the following reaction.
21. Show the mechanism for the following reaction.
22. Identify A-J in the following reaction sequence.
