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Solutions_Manual_for_Organic_Chemistry_6th_Ed 219

Solutions_Manual_for_Organic_Chemistry_6th_Ed 219 - 1 0-4(a...

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Unformatted text preview: 1 0-4 (a) 8,8-dimethylnonane¡2,7 ¢diol () octane¢L£8¤diol (c) CIs¤cyclohex-2¢ene¢¥£4¤diol (d) 3¤cyc¦opentylheptane¢2,§¤diol (e) TrNs-cyc¨obutane¤¥£3¢diol ©0ª5 «heRe aRe fouR St¬uctuRa¨ featuReS to conSideR when Dete­®ning Solubi¦ity in WateR: ¯° mo¦ecu¦eS w±th FeweR ²aRBon³ W´µ¶ Be MoRe SoµuBµe ´n Wa·eR ¸aSSu¹´ºG o·He» ·¼´ºG½ BE´ºG equA¾¿; 2¡ BÀAº²ÁED o o·Heô½E comPa²t StRuctuReS ÄRe MoRe Solub¦e than lineaR StRuctuReSÅ 3) ÆoRe ¼ydRogen-bond±ng gRouPS wi¨l ±ncReaSe So¨ubil±tyÅ 4) an ±on±c foRm of a comPound Wi¦¨ be moRe So¦uble in wateR than the nonionic ÇoRM. Èa) Éyclo¼eXano¨ iS ÊoRe So¨ub¦e becauSe ±tS a¨ky¨ gRouP ±S moRe compact than ±n Ë¢ÌeXano¦. (b) 4-Íethylpheno¨ iS moRe So¦uble becauSe itS ¼yDRocaRÎon PoÏtion iS moRe comPact than ±n Ð-hePtano¨, anD pheno¦S ÇoRm PaÏticu¨aR¨y StRong hydRogen bondS w±t¼ wateRÑ Òc) 3¤Óthylhexan-3-ol ±S moRe Soluble becauSe itS alky¨ PoÔ±on ±S ÕoRe Sp¼eR±ca¨ than in octanÖ2-×ØÙ...
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