Lect33_1111 - 7. Conversion of Alcohols into Alkyl Halides...

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Ch. 11 - 2 7. Conversion of Alcohols into Alkyl Halides H X ( X = Cl , Br , I ) P Br 3 SO Cl 2 R OH R X
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Ch. 11 - 3 8A. 8A. Mechanisms of the Reactions of Mechanisms of the Reactions of Alcohols with HX Alcohols with HX Secondary, tertiary, allylic, and benzylic alcohols appear to react by a mechanism that involves the formation of a carbocation Primary alcohols and methanol react to form alkyl halides under acidic conditions by an S N 2 mechanism
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Ch. 11 - 4 8. Alkyl Halides from the Reaction of Alcohols with Hydrogen Halides The order of reactivity of alcohols 3 o The order of reactivity of the hydrogen halides HI > HBr > HCl (HF is generally unreactive) R OH R X H X ++ H 2 O > 2 o > 1 o > methyl
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Ch. 11 - 5 9. Alkyl Halides from the Reaction of Alcohols with PBr 3 or SOCl 2 Reaction of alcohols with PBr 3 RO H RB r 3 ++ H 3 PO 3 PBr 3 (1 o or 2 o ) The reaction does not involve the formation of a carbocation and usually occurs without rearrangement of the carbon skeleton (especially if the temperature is kept below 0°C)
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Ch. 11 - 6
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This note was uploaded on 02/20/2012 for the course CHEM 333 taught by Professor Lavigne during the Fall '09 term at South Carolina.

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Lect33_1111 - 7. Conversion of Alcohols into Alkyl Halides...

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