215F07-notes-9-19-07 - Chem 215 F07 Notes Dr Masato Koreeda...

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Chem 215 F07 Notes – Dr. Masato Koreeda - Page 1 of 3. Date: September 19, 2007 Chapter 13. Alcohols, Diols, and Ethers: V. Reactions of alcohols: Alcohols to alkyl halides Vb. With SOCl 2 (thionyl chloride) or PBr 3 (phosphorus tribromide) (continued) Mechanism for an alcohol to the chloride with SOCl 2 /pyridine + + O H H S H Cl R Cl SO 2 (gas) S N 2 product S O Cl Cl N S O Cl O H H S O Cl Cl O H H S O Cl N B or O H S O Cl Cl highly electrophilic S Alternatively, that can be formed from SOCl 2 and pyridine may be the reagent that puts S(=O)Cl onto the OH group. *Similar reactions and mechansims for the formation of bromides from alcohols with PBr 3. BH N H or VI . Ethers (R – O – R’) 1. Synthesis + R O R' X a.Williamson synthesis R O R' ether X S N 2 reaction R’ - X: alkyl halides (usually bromide and iodide, sometimes chloride) or tosylates R’: usually primary; methyl, allyl (CH 2 =CH-CH 2 - ), benzyl (PhCH 2 -). + + + + H O CH 2 CH 3 O NaH (1 mol equiv) I CH 2 CH 3 (excess; typically, 1.5 mol equiv) + H 2 + NaI H Na O Na H 2 C CH 3 I Mechanism: H H (gas) (gas)
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