ZLM-chapter 10-alcohol

ZLM-chapter 10-alcohol - LMZ/CHEM109A/ Winter 2010 Chapter...

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LMZ/CHEM109A/ Winter 2010 Chapter 10: Reactions of alcohols, amines, ethers, epoxides and sulfur-containing compounds I. Nucleophilic substitution reactions for the conversion of alcohols to other functional groups A. Introduction: B. Conversion of alcohol to alkyl halide (Reaction at C-O bond) (sec. 11.1): in-situ converting OH into good leaving groups 1. Conversion of alcohol to alkyl bromide by reaction with HBr (or NaBr, H 2 SO 4 ) R * OH + HBr + H 2 O racemic mixture S N 1 R * Br R * OH + HBr + H 2 O inversion S N 2 R * Br Mechanism? 2. Conversion of alcohol to alkyl chloride by reaction with Lucas reagent (HCl, ZnCl 2 ) R * OH + HCl + H 2 O racemic mixture S N 1 R * Cl R * OH + HCl + H 2 O inversion S N 2 R * Cl ZnCl 2 ZnCl 2 Mechanism? 3. Reaction of alcohols (especially 1° or 2°) with thionyl chloride (Sec. 11.9) R R' H OH R R' H X R' = H or alkyl or aryl stereochemistry?? SOCl 2 (+ SO 2 + HCl) Mechanism? 4. Reaction of alcohols (especially 1° or 2°) with phosphorus halide (Sec. 11.8) R R' H OH R R' H X R' = H or alkyl or aryl inversion for 1° and 2° C PCl 3 , PBr 3 , or PCl 5 (+ HO PX 2 X= Br or Cl)
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This note was uploaded on 03/01/2010 for the course CHEM 109A taught by Professor Bruice during the Spring '07 term at UCSB.

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ZLM-chapter 10-alcohol - LMZ/CHEM109A/ Winter 2010 Chapter...

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