Ch_322a_11.012 - Conversion of Alcohols into Alkyl Halides...

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Conversion of Alcohols into Alkyl Halides A common synthetic transformation is the conversion of an alcohol into an alkyl halide: R OH R X There are numerous reagents for this conversion including hydrogen halides (HX), phosphorous halides (PX 3 ) and thionyl chloride (SOCl 2 ).
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Hydrogen Halide Reagents The conditions needed for preparing alkyl halides with HX reagents depends on the structure of the R group and HX. HBr (stronger acid) is more reactive than HCl. CH 3 CH 2 CH 2 CH 2 OH butyl alcohol dry HBr gas or NaBr, H 2 SO 4 reflux CH 3 CH 2 CH 2 CH 2 Br butyl bromide CH 3 CH 2 CH 2 OH propyl alcohol HCl/ZnCl 2 reflux CH 3 CH 2 CH 2 Cl propyl chloride CH 3 C OH CH 3 CH 3 conc. HCl 25 o C CH 3 C Cl CH 3 CH 3 tert-butyl alcohol tert-butyl chloride
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Some Observations (A) Catalysis by Acid Addition of acids stronger than HX (such as H 2 SO 4 ) speeds up the reaction. (B) Carbocation Rearrangements These rearrangements are common except with most primary alcohols.
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