chm2211ch14notes - Ch. 14 page 1 Chapter 14 Ethers,...

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Ch. 14 – page 1 Chapter 14 – Ethers, Epoxides, and Sulfides CHM 2211 – Davidson 1. Introduction and Physical Properties Recall that ether functional group is R-O-R’, where R and R’ can be the same or different Structure is sp 3 hybridized at oxygen, with bond angle approximately 110º so polar Ethers have low boiling points – why? Compare to alcohol of same molecular weight (Table 14.1) Can participate in hydrogen bonding using lone pairs of electrons on oxygen Ethers are used as solvents in organic chemistry o relatively non-reactive o good solubility of organics o solvation of cations o complexation to electrophiles – THF:BH 3 Crown ethers – cyclic ethers that specifically solvate metal cations due to size of ring O O O O O O O O O O O O O O O 12-crown-4 15-crown-5 18-crown-6 Li + Na + K +
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Ch. 14 – page 2 2. Nomenclature of Ethers IUPAC rules are presented in section 14-3 – become familiar with these Consider the following molecules… 3. Synthesis of Ethers a) The Williamson Ether Synthesis This is a review of reactions learned in Ch. 11 on alcohols Ether formed through S N 2 attack of alkoxide on alkyl halide Example
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Ch. 14 – page 3
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chm2211ch14notes - Ch. 14 page 1 Chapter 14 Ethers,...

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