Solutions_Manual_for_Organic_Chemistry_6th_Ed 74

Solutions_Manual_for_Organic_Chemistry_6th_Ed 74 - 4-22...

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Unformatted text preview: 4-22 continued (b) CH3 CH3 I I h C - CO - h 3 I + O R -h CCO3 I + Rh an alkyl CH3 raDIcal CH3 When the ALcoho hYrogen i s AbstrActe from TbUtY Acoho , A e Atively stAbe T-bUtoxY rAicA ( (CH3)3CO 0 ) is prodUceD. hi s ow energY adicAl is slower to reAct thAn AlKY rAdicas, moderAting the reAction And ProdUcing ess " knocking" 43 (A) 1 H AbstractIon F 0 + Ch3Ch2CH3 breAK 1 H cH2CH2cH3 mAKe HF overA H AbstrAction 2 H AbstrAction F 0 + CH3C2Ch3 breAK H CH(Ch32 mAke HF overAll H AbstrActIon H F + M0 = + 4 1 KJ/mole ( + 98 kcAj/mole) M0 = 569 k/oe 1 36 Kcal/ole Mo -159 kJ/mole ( 38 kcaLmole) H F mO + 397 K/mole + 95 KcAole m = -569 KJ/mole 36 kcal/mole M -172 kJ/mole ( -41 kcamole) (b) FuorinAtion is extremey exothermc And is iKelY to be indiscnate in which hyDrogens Are AbstrActed (n fAct Cc bonDs Are Aso broKen duing fuorInAtIon)...
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