Solutions_Manual_for_Organic_Chemistry_6th_Ed 83

Solutions_Manual_for_Organic_Chemistry_6th_Ed 83 - In...

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4-50 Two mechanisms are possIble depending on whether HO' reacts with chLorIne or wI±h cyc!opentane. MechanIs² 1 1 < 1) HO-O³ 2 HO' InItia±Ion (2) HO' + Cl ´Cl ²³ µO-C¶ + Cl' :> H f) Cl· ¸ ´µ H-¹l + ' propagation H H (4) ¹l ´¹l + ± ²³ ¹l ² + ¹l' Mechanism 2 f ) HOºOH ¶· 2 HO' initiation ³´ ³ µ (2) HO' + ´µ H-OH + H H ¹l ´Cl + ¸¹ · ¸ ¹l· propagatIon ¸¹ ³ (4) ¹l¼ + ´µ H-¹l + D The energies of the propagation steps deter½ne which mechanism Is followed. The bond dIssocia±Ion energY of HO¾¹l is aBout 2±0 kJ/mole (aBout 50 kcal¿mole), makÀng inItIation step ²2) in ²echanism 1 endotheN±ic BY aBoUt 30 kj/mole (aBoUt 8 kcal¿mole)Á
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Unformatted text preview: In mechaNism 2, Initia±ion s±ep ²2) Is exothe²ic BY aBout ³0 ³ Kj/mole (24 kcal¿mole); mecÂanÃsm 2 is prefeRedÄ 4´51 ± C l _ ¹l ±c: ¹l ŹÆH + :Odz º» H ÈO ± ¹l ´¹: ¼½ I Uº I i H H H a carBene 4µ52 This ÉÊitical eqUation Is the keY to this proBlemË 1 G = 1 h ´ T 1 S At 1400 ÌÍ the equiLiBÊIu² constant is 1; thereforeÎ c f G = 0 > ¸ Assuming f H Is aBout ±he same at 1400 Ì as it is at caloÊimeter tempera±ureÏ -137 kÐ/mole = 14¶0 Ì = ·±37¸000 1400 ¾ Ñ98 Ò/ÌÓmole (-23 cal¿ÌÔmole) jÕÖmole . . :¹L : This is a large decrease in entropYÍ consIstent wit two molecules comBining into one× 75...
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