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Ch_322b_16.03 - Chapter 16.3 lecture note

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Syntheses of Ketones Industrial Scale Many simple ketones are important industrial chemicals that find use as solvents or reagents for the syntheses of more complex materials. An example of an important industrial process is the synthesis of acetone and phenol by the oxidation of isopropylbenzene (cumene). Petroleum is the source of the hydrocarbon starting materials.
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Petroleum benzene annual US production over 12 billion pounds CH 3 CH=CH 2 propene annual US production over 26 billion pounds CH CH 3 CH 3 cumene annual US production close to 6 billion pounds O 2 C CH 3 CH 3 OOH cumene hydroperoxide H 3 O + OH phenol + CH 3 CCH 3 O = acetone over 4 billion pounds close to 3 billion pounds annual US productions
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Laboratory Syntheses of Ketones Several standard synthetic methods were covered in earlier chapters. Oxidation of Secondary Alcohols H OH cyclohexanol K 2 Cr 2 O 7 or CrO 3 H 2 SO 4 O = cyclohexanone These oxidations generally proceed well with little side reactions. Aryl Ketones by Friedel-Crafts Acylation CH 3 CH 2 CH 2 CCl O = + butanoyl chloride AlCl 3 CCH 2 CH 2 CH 3 O = phenyl propyl ketone
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However, electron-deficient aromatics will not react. NO 2 CCl = + AlCl 3 NO 2 C = m-nitrobenzophenone OK O O NO 2 + CCl O = AlCl 3 X Ozonolysis of Alkenes CH 3 CH 3 1,2-dimethylcyclopentene O 3 CH 2 Cl 2 , -78 o C Zn H 2 O CH 2 CH 2 CCH 3 CH 2 CCH 3 O = = 2,6-heptanedione O
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