Organic 2 Review Problem 106

Organic 2 Review Problem 106 - 9o P RACTICAL O RGANIC C...

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9 o PRACTICAL ORGANIC CHEMISTRY Chloroform. CHCl 3 . When chlorine is passed into boiling ethanol, both chlorination of the methyl group and oxidation of the primary alcohol group to an aldehyde occur, giving trichloro-acetaldehyde or chloral: CH 3 CH 2 OH + 4 C1 2 -> CCl 3 CHO r 5 HC1 When chloral is treated with caustic alkali, fission of the C-C linkage occurs, giving chloroform and a formate: CCl 3 CHO -f- KOH -> CHCI 3 + HCOOK Acetaldehyde and also many ketones, such as acetone, containing the CH 3 CO- group behave similarly when treated with bleaching powder, chlorination of the CH 3 CO- group being immediately followed by fission of the molecule by the alkali present in the bleaching powder: CH 3 COCH 3 -f 3 C1 2 -> CCI 3 COCH, -f CHCl 3 2CCl 3 COCH 3 -u Ca(OH), — 2CHCl 3 f (CH 3 COO) 2 Ca The acetone method clearly gives a much cheaper product than the ethanol method. Required: Bleaching powder, ioo g.; acetone, 44 ml. Place ioo g. of bleaching powder in a mortar and add 250 ml.
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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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