Chapter 18: 18-18-7P b (page 575)
Predict the products of the following reactions:
b) The product of the reaction is,
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How would you prepare the following compounds from 1-phenylethanol?
(a)Methyl 1-phenylethyl ether (b) Phenylepoxyethane
(c)tert-Butyl 1-phenylethyl ether (d) 1-Phenylethanethiol
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.
Safrole, a substance isolated from the oil of sassafras, is used as a perfumery agent. Propose a synthesis of safrole from catechol (1,2-benzenediol).
Predict the products of the following reactions:
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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