The reactions shown in Fig. P10.67 all involve conversion of the alcohol oxygen into a good leaving
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The reactions shown in Fig. P10.67 all involve conversion of the alcohol oxygen into a good leaving group, followed by the reaction of the resulting compound with a nucleophile provided by the reagent. Write curved-arrow mechanisms for each reaction.
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(a) (b) OH CH3CH₂CHCH₂CH3 + PBr3 (PhO)3P: +H3C-I triphenyl- phosphite Ph3P: CBr4 + triphenyl- phosphine Figure P10.67 [X] an ionic compound Br CH,CH,CHCH,CH3 + HO—PBI, OH OH :Ö -I + (PhO)₂P-CH3 + PhOH pK₂ = 10 Br :0 + Ph3P+ + HCBr3 triphenyl- bromoform (pK₂ = 24) phosphine oxide
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