Organic 2 Review Problem 255

Organic 2 Review Problem 255 - PREPARATIONS 239 ca. 10 ml....

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PREPARATIONS 239 ca. 10 ml. of chloroform to remove sticky impurity. Weight of crude dark yellow product, 3 g. Recrystallise from xylene or from a much greater volume of chloroform. The i,8-diphenyl- octatetrene is obtained as bright yellow crystals, m.p. 228°. Yield, 2 g. If the preparation is carried out on a much larger scale, mechanical stirring of the heated mixture is advisable. Since the octatetrene contains two -CH: CH-CH: CH- units, it will readily combine with two molecules of maleic anhydride and other adducts by the Diels-Alder reaction (p. 292). Benzoic Acid, C 6 H 5 COOH, from Benzyl Chloride, C 6 H 5 CH 2 Cl. When an aromatic compound having an aliphatic side chain is subjected to oxidation, fission of the side chain occurs between the first and second carbon atoms from the benzene ring, the first carbon atom thus becoming part of a carboxyl ( -COOH) group. For example: C 8 H 5 CH 8 > C 8 H 6 COOH C 6 H 5 CH 2 CH 3 > C 6 H 6 COOH C 6 H 6 COCH 1 > C 8 H 6 COOH C 6 H 6 CH:CH'COOH
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This note was uploaded on 09/19/2011 for the course CHM 2211 taught by Professor Castalleano during the Fall '06 term at University of Florida.

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