Ch_322b_15.15

Ch_322b_15.15 - was known to August Kekule' and other...

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Oxidation of the Side Chain of Arenes Strong oxidizing agents oxidize alkyl and alkenyl side chains to aryl carboxylic acids . A standard reagent is hot alkaline potassium permanganate . CH 3 CH 3 p-xylene (i) KMnO 4 , KOH, heat (ii) H 3 O + COOH COOH terephthalic acid CH 2 CH 2 CH 2 CH 3 CH 3 1-p-tolylbutane (i) KMnO 4 , KOH, heat (ii) H 3 O + COOH COOH
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Other Vigorous Side-Chain Oxidations C 6 H 5 CH=CHCH 3 C 6 H 5 C CCH 3 C 6 H 5 CCH 2 CH 3 O = (i) KMnO 4 , KOH, heat (ii) H 3 O + alkenyl alkynyl acyl COOH benzoic acid The resistance of the benzene to strong oxidation conditions
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Unformatted text preview: was known to August Kekule' and other chemists of the late 19th century. For many years, this chemistry was used for structural analyses. CH 3 CH 3 H 3 C CH 2 CH 3 CH 3 CH 2 CH 2 CH 3 III CH(CH 3 ) 2 or Quiz 15.015 Three isomeric substituted benzenes of formula C 9 H 12 are oxidized vigorously producing the carboxylic acid products below. Provide structures for I, II and III. [Ox] COOH COOH HOOC I [Ox] COOH COOH II [Ox] COOH III...
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Ch_322b_15.15 - was known to August Kekule' and other...

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