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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 with cyc!opentane. Mechanism 1 1 < 1) HO-OH -- - 2 HO' initiation (2) HO' + Cl -Cl -- -- HO-Cl + Cl' :>0 H f) Cl· + -- -- H-Cl + '0 propagation H H (4) Cl -Cl + '0 -- -- Cl >O + Cl' Mechanism 2 f ) HO-OH --- 2 HO' initiation :>0 H 'O (2) HO' + -- -- H-OH + H H f) Cl -Cl + '0 --- CI >O + Cl· propagation :>0 H (4) Cl' + -- -- H-Cl + D The energies of the propagation steps determine which mechanism is followed. The bond dissociation energy of HO-Cl is about 210 kJ/mole (about 50 kcallmole), making initiation step (2) in mechanism 1 endothennic by about 30 kJ/mole (about 8 kcallmole).
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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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