Reaction Review 20 - Substitution of Alcohols Using SOCL2 PCl3 PBr3 PI3 PDF

Title	Reaction Review 20 - Substitution of Alcohols Using SOCL2 PCl3 PBr3 PI3
Course	Introduction To Organic Chemistry I
Institution	University of North Carolina at Chapel Hill
Pages	2
File Size	189.2 KB
File Type	PDF
Total Downloads	102
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Download Reaction Review 20 - Substitution of Alcohols Using SOCL2 PCl3 PBr3 PI3 PDF

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Rxn Review #20 - Substitution of Alcohols using SOCl2 or PBr3, PCl3, PI3 The general reaction = converts alcohol to alkyl halide

ROH + reagent  R-X (alkyl halide) In certain situations (solvent, reaction conditions), it’s more effective to use these reagents to convert alcohols to alkyl halides than using H-X. All of these reagents react by first converting the bad leaving group (LG), -OH, into a good LG. These reagents are used to convert methyl, 1o and 2o alcohols into alkyl halides, and they do so using an SN2 reaction mechanism. They give poor yields with 3o alcohols and hence are not used with those. No rearrangements observed with 2o alcohols since no carbocation in mechanism Mechanism for SOCl2 reaction with methanol:

PCl3, PBr3 and PI3 reacts similarly (to SOCl2) with 1o and 2o alcohols to give alkyl chlorides, alkyl bromides and alkyl iodides. See mechanism below. Turning propanol into bromopropane using PBr3...