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Lect34_1111 - 11E Silyl Ether Protecting Groups A hydroxyl...

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Ch. 11 - 1 11E. 11E. Silyl Silyl Ether Protecting Groups Ether Protecting Groups A hydroxyl group can also be protected by converting it to a silyl ether group 1 2 3 4 5 1 2 3 5 6 4 6
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Ch. 11 - 2 Direct reaction will not work (Not Formed) Instead
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Ch. 11 - 3 Need to “protect” the –OH group first
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Ch. 11 - 4 12. Reactions of Ethers Dialkyl ethers react with very few reagents other than acids
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Ch. 11 - 5 12A. 12A. Cleavage of Ethers Cleavage of Ethers Heating dialkyl ethers with very strong acids (HI, HBr, and H 2 SO 4 ) causes them to undergo reactions in which the carbon–oxygen bond breaks Cleavage of an ether
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Ch. 11 - 6 13. Epoxides Epoxide (oxirane) A 3-membered ring containing an oxygen
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Ch. 11 - 7 13A. 13A. Synthesis of Synthesis of Epoxides Epoxides : : Epoxidation Epoxidation Electrophilic epoxidation
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Ch. 11 - 8 13B. 13B. Stereochemistry of Stereochemistry of Epoxidation Epoxidation Addition of peroxy acid across a C=C bond A stereospecific syn ( cis ) addition
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Ch. 11 - 9 O O H O R Mechanism O O H O R O O H O R peroxy acid alkene concerted transition
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