Chapter 17 September 26 - Formation and use of an alkyl...

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1 Mechanism Review: E 1
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2 Dehydration of Alcohols using Phosphorus Oxychloride: Example: Mechanism: Allows for the dehydration of alcohols at much lower temps (less harsh conditions) *** The Book is Incomplete ***
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3 Conversion of Alcohols into Alkyl Halides: Tertiary alcohols (review):
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4 Conversion of Alcohols into Alkyl Halides (cont'd): Primary and secondary alcohols: Examples: Mechanisms:
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5 Conversion of Alcohols into Tosylates: p­toluenesulfonyl chloride (tosyl chloride) Sample Reaction: Mechanism:
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6 Important Stereochemical Considerations of These Reactions
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Unformatted text preview: Formation and use of an alkyl halide intermediate results in retention of configuration Use of a pTosCl intermediate results in the inversion product We now have a way to exert stereochemical control! 7 Oxidation of Alcohols Primary Secondary Tertiary 8 Typical Oxidizing Reagents: Potassium Permanganate: Chromium Trioxide: Sodium Dichromate: Pyridinium Chlorochromate: Oxidizes 1 o OH to an aldehyde and stops...
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This note was uploaded on 12/20/2011 for the course CHEM 234-54 taught by Professor Morrison during the Fall '09 term at University of Georgia Athens.

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Chapter 17 September 26 - Formation and use of an alkyl...

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