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noltaalcohol - The final few recipes from Ch 12 and a...

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C OH R OH C OH C X C X C Cl C Br C X C C O CH 3 H H 3 C H 3 CH 2 C C C OH CH 3 H H 3 C H 3 CH 2 C C C HO CH 3 H H 3 C H 3 CH 2 C X X The final few recipes from Ch. 12 and a general review of important topics Ch. 12 recipes I. Ways of replacing an -OH group with a halogen 1 o R OH 2 o 3 o R O - 1.TsCl pyridine 2. Na + X - R-Cl (SN2) R' lg R-Br (SN2) R-X (SN2) R O 1.TsCl pyridine 2. Na + X - R' OH lg O II. Opening oxiranes 1. H 3 O + 2. Na + X - O 1.Na + X - 2.H 3 O + H R NOTE: The nucleophile adds to the C which is most substituted, anti to the O of the oxirane Acid-catalyzed ring opening NOTE: The nuclophile goes to the least hindered C of the ring, acid is added after to protonate the O - . Need a strong nucleophile. Nucleophilic ring opening X can be any nucleophile: halides, OH - , water, etc. III. Making and Breaking ethers 1. First deprotonate an OH to make a good nucleophile Na + H - Na + NH 2 - Na or K
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