Lect35_1114 - 17. Summary of Reactions of Alkenes, Alcohols...

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Ch. 11 - 1 17. Summary of Reactions of Alkenes, Alcohols and Ethers Synthesis of alcohols OH (1 o alcohol) X OH 1. BH 3 THF 2. H 2 O 2 , NaOH MgBr 1. 2. H 2 O O
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Ch. 11 - 2 Synthesis of alcohols OH (2 o alcohol) 1. BH 3 THF 2. H 2 O 2 , NaOH 1. Hg(OAc) 2 ,H 2 O 2. NaBH 4 or H + , H 2 O
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Ch. 11 - 3 Synthesis of alcohols (3 o alcohol) OH H 2 O X 1. Hg(OAc) 2 ,H 2 O 2. NaBH 4 H + , H 2 O
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Ch. 11 - 4 Reaction of alcohols OH (1 o alcohol) OR 1. base 2. R-X H + , heat OTS TsCl pyridine SOCl 2 Cl X H-X Br PBr 3
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Ch. 11 - 5 Synthesis of ethers RO R R OH conc. H 2 SO 4 140 o C R X RO Cleavage reaction of ethers R ' HX X ROH + R'X R ' H
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HO H H more stable 3 o cation slow (step 1) H H 2 O fast (step 2) H O HH H 2 O fast (step 3) H OH + H H Mechanism of Acid Catalyzed Hydration Mechanism of Acid Catalyzed Hydration
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HgOAc + AcO HO HgOAc O HgOAc H H Mechanism of Mechanism of Oxymercuration Oxymercuration Does not undergo a “free carbocation” OAc Hg OAc H 2 O H 2 O
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Ch. 8 - 8
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This note was uploaded on 02/20/2012 for the course CHEM 333 taught by Professor Lavigne during the Fall '09 term at South Carolina.

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Lect35_1114 - 17. Summary of Reactions of Alkenes, Alcohols...

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