Chapter 18 September 30 - alkoxide with the less hindered...

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1 Ether Nomenclature: Method 1: Method 2: In the case of simple ethers with no other functional groups, name the two organic groups and add "ether" to the end If other functional groups are present, the ether portion is considered a substituent (alkoxy group)
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2 Structure and Physical Properties of Ethers: Bond angles are approx. 112 o Oxygen atom is sp 3 hybridized Boiling points are comparable with similar alkanes (MW and branching)
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3 Formation of Ethers Acid Catalyzed Dehydration of Alcohols: Williamson Ether Synthesis: General Reaction Formation of the metal alkoxide, followed by S N 2 displacement of the leaving group Metal alkoxide + 1 o alkyl halide/tosylates Unsymmetrical ethers should be synthesized by reacting the more hindered
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Unformatted text preview: alkoxide with the less hindered alkyl halide/tosylate 4 Practice Problems: 5 Alkoxymercuration of Alkenes Example: Limitation: Very similar to oxymercuration reaction from Chapter 7 Markovnikov addition of the alcohol group to form the ether 6 Choose Your Path To Ether Bliss: 7 Reactions of Ether: 1. Acidic Cleavage General Reaction: Reaction Specifics Ethers Containing Primary and/or Secondary Alkyl Groups: Ethers Containing Tertiary Alkyl, Benzylic or Allylic Groups: Ethers are generally inert and therefore useful as reaction solvents Strong acids will cleave them however:...
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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 18 September 30 - alkoxide with the less hindered...

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