FGI - FUNCTIONAL GROUP INTERCONVERSIONS Functional Group...

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FUNCTIONAL GROUP INTERCONVERSIONS 119 Functional Group Interconversions C&S Chapter 3 #1; 2; 4a,b, e; 5a, b, d; 6a,b,c,d; 8 1 sulfonates 2 halides 3 nitriles 4 azides 5 amines 6 esters and lactones 7 amides and lactams Sulfonate Esters - reaction of an alcohols (1° or 2°) with a sulfonyl chloride R OH R O S O O R' CH 3 CF 3 CH 3 R'SO 2 Cl sulfonate ester R'= mesylate triflate tosylate - sulfonate esters are very good leaving groups. Elimination is often a competing side reaction Halides - halides are good leaving groups with the order of reactivity in S N 2 reactions being I>Br>Cl. Halides are less reactive than sulfonate esters, however elimination as a competing side reaction is also reduced. - sulfonate esters can be converted to halides with the sodium halide in acetone at reflux. Chlorides are also converted to either bromides or iodides in the same fashion (Finkelstein Reaction). R O S O O R' R X X - X= Cl, Br, I R Cl R I NaI, acetone reflux - conversion of hydroxyl groups to halides: Organic Reactions 1983 , 29 , 1 R OH R X - R-OH to R-Cl - SOCl 2 - Ph 3 P, CCl 4 - Ph 3 P, Cl 2 - Ph 3 P, Cl 3 CCOCCl 3
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FUNCTIONAL GROUP INTERCONVERSIONS 120 - R-OH to R-Br - PBr
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FGI - FUNCTIONAL GROUP INTERCONVERSIONS Functional Group...

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