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.
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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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How would you synthesize racemic disparlure (Problem 18-63) from compounds having ten or fewer carbons?
How would you prepare the following ethers using a Williamson synthesis?
The 1H NMR spectrum shown is that of a cyclic ether with the formula C4H8O. Propose a structure.

Disparlure, , is a sex attractant released by the female gypsy moth, Lymantria dispar. The NMR spectrum of disparlure shows a large absorption in the alkane region, 1 to 2 d, and a triplet at 2.8 d. Treatment of disparlure, first with aqueous acid and then with , yields two carboxylic acids identified as undecanoic acid and 6-methyl- heptanoic acid. ( ,cleaves 1, 2-diols to yield carboxylic acids). Neglecting stereochemistry, propose a structure for disparlure. The actual compound is a chiral molecule with 7R, 8S stereochemistry. Draw disparlure, showing the correct stereochemistry.
How would you prepare the following ethers using a Williamson synthesis?
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