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 - C¡O - h 3 I + O R -h C¢C¡O£3 I + R¤h an alkyl CH3 raDIcal CH3 When the ALcoho¡ hY¢rogen i s AbstrActe¢ from T£bUtY¡ A¤coho¤ , A ¥e¤ Atively stAb¤e T-bUtoxY rA¢icA¤ ( (CH3)3C¥O 0 ) is prodUceD. ¦hi s ¡ow energY ¥adicAl is slower to reAct thAn AlKY¡ rAdica¡s, moderAting the reAction And ProdUcing ¡ess " knocking§" 4¨©3 (A) 1 ° H AbstractIon F 0 + Ch3Ch2CH3 breAK 1 ° H ¦cH2CH2cH3 mAKe HªF overA«« ¬ ° H AbstrAction 2° H AbstrAction F 0 + CH3C§2Ch3 breAK ©° H ¨CH(Ch3©2 mAke HªF overAll ©° H AbstrActIon H ­ F + M0 = + 4 1 ® KJ/mole ( + 98 kcAj/mole) M0 = ª 569 k¯/±o²e ³ª 1 36 Kcal/±ole´ Mo ¡ -159 kJ/mole ( ¡38 kcaLmole) H­ F mO ¢ + 397 K¯/mole µ + 95 KcA¶±ole· m¡ = -569 KJ/mole ¸ª ¹ 36 kcal/moleº M¢ ¡ -172 kJ/mole ( -41 kca¢mole) (b) F¤uorinAtion is extreme¡y exotherm»c And is ¡iKelY to be indisc¼±»nate in which hyDrogens Are AbstrActed½ (¾n fAct¿ C¥c bonDs Are A¡so broKen duÀing f¡uorInAtIon½)...
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This note was uploaded on 02/27/2010 for the course CHEM 140 taught by Professor Wade during the Spring '10 term at Whitman.

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