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Unformatted text preview: regenerating the sulphuric acid: C 2 H 5 HSO 4-f HOC 2 H 5-> C 2 H 5 OC 2 H 5 + H 2 SO 4 (3) If the mixture contains a considerable excess of sulphuric acid and is heated to 160-170, the ethyl hydrogen sulphate breaks down, giving ethylene and again regenerating the sulphuric acid. C 2 H 5 HSO 4 = C 1 H 4 + H 2 SO 4 The mechanism of the formation of these three compounds is based on the initial reaction between ethanol and a strong acid such as sulphuric acid, which involves protonation of the ethanolic oxygen to form the ion (I). + CH 3 CH 2 OH r H 2 SO 4-^ CH 3 CH 2-OH [- HSO 4 (I) H This ion (I) can react in three ways, according to the conditions. (a) reaction with the HSO 4 may give ethyl hydrogen sulphate CH 3 CH-OH -f HSO 4- CH 3 CH 2 OSO 3 H - H 2 O H (b) reaction with ethanol gives diethyl ether H- -L-CH 3 CH 2-OH- CH 3 CHoOH-~ CH 3 CH 2 OCH 2 CH n H 2 O -H H (c) dehydration gives ethylene CH 3 CHoOH-CH, -CH, H,() H H...
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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.
- Fall '06
- Organic chemistry