Chapter 18: 18-18-1P c (page 570)
Name the following ethers:
c)

Short Answer
c) The name of the given ether is p-Bromomethoxybenzene.
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Chapter 18: 18-18-1P c (page 570)
Name the following ethers:
c)

c) The name of the given ether is p-Bromomethoxybenzene.
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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.
Identify the reagents a-e in the following scheme:

Anethole, , a major constituent of the oil of anise, has the NMR spectrum shown. On oxidation with , anethole yields p-methoxybenzoic acid. What is the structure of anethole? Assign all peaks in the NMR spectrum, and account for the observed splitting patterns

Predict the product(s) and provide the mechanism for each two-stepprocess below.




When 2-methyl-2,5-pentanediol is treated with sulfuric acid, dehydration occurs and 2,2 dimethyltetrahydrofuran is formed. Suggest amechanism for this reaction. Which of the two oxygen atoms is mostlikely to be eliminated, and why?

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