Chapter 18: Q15P (page 584)
15-Crown-5 and 12-crown-4 ethers complex Na+ and Li+, respectively. Make models of these crown ethers, and compare the sizes of the cavities.
Short Answer
Answer
Chapter 18: Q15P (page 584)
15-Crown-5 and 12-crown-4 ethers complex Na+ and Li+, respectively. Make models of these crown ethers, and compare the sizes of the cavities.
Answer
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Get started for freeMethyl aryl ethers, such as anisole, are cleaved to iodomethane and aphenoxide ion by treatment with LiI in hot DMF. Propose a mechanismfor this reaction.
The alkoxymercuration of alkenes involves the formation of an organomercury intermediate (I), which is reduced with NaBH4 to give an etherproduct. For each reaction below, predict the ether product and provide the mechanism formation.
(a)
(b)
(c)
How would you synthesize racemic disparlure (Problem 18-63) from compounds having ten or fewer carbons?
Propose structures for compounds that have the following 1H NMR spectra:
(a)
(b)
Griginard reagents react with oxetane, a four membered cyclic ether, to yield primary alcohols, but the reaction is much slower than the corresponding reaction with ethylene oxide. Suggest a reason for the difference in reactivity between oxetane and ethylene oxide.
Oxetane
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