slide9 - i.e., within bonding distance. The chain must be...

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Where We Are Going Today x Chapter 9 – Further Reactions of Alcohols and the Chemistry of Ethers Reactivity Modes of Alcohols Conversion to Alkoxides Protonation to Give Alkyloxonium Ions Dehydration of Alcohols Carbonium Ion Rearrangements Hydride Shifts Alkyl Shifts Conversion to Good Leaving Groups Conversion to Alkyl Halides
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Where We Are Going Today x Chapter 9 – Further Reactions of Alcohols and the Chemistry of Ethers Chemistry of Ethers Nomenclature illiamson Ether Synthesis Williamson Ether Synthesis Cyclic Ether Formation and Epoxides Reactions of Acyclic Ethers Reactions of Epoxides Thiols and Thioethers
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Reactivity Modes of Alcohols
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Orbital Description of 1,2-Hydride Shifts
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Two Key Factors Involved in Ring Formation x Entropy Factor – the reacting sites need to be close to one another,
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Unformatted text preview: i.e., within bonding distance. The chain must be in a certain orientation for this to occur and many degrees of freedom of the chain must be sacrificed (entropy is overcome) in order to get the two reacting centers close to one another. This entropy factor becomes less and less favorable as the chain between the alcohol and the halide becomes longer. x Proximity Factor In the formation of a three-membered ring the two reacting sites are already very close together. So, some of the energy barrier that must be overcome to get the two reacting centers close (like in a typical intermolecular S N 2) is already overcome by the proximity of the two groups. This proximity effect is really only significant in three-membered ring formation....
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This note was uploaded on 01/25/2010 for the course CHEM chem 140A taught by Professor Dr.yang during the Spring '07 term at UCSD.

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slide9 - i.e., within bonding distance. The chain must be...

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