Chapter_11_(Wade)

Chapter_11_(Wade) - ORGANIC CHEMISTRY CHEM 12A LANEY...

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ORGANIC CHEMISTRY LANEY COLLEGE CHEM 12A INSTRUCTOR: S. CORLETT Chapter 11 Learning Objectives and Terminology Common reactions of alcohols include dehydration, oxidation, substitution, esterification, tosylation and formation of ethers of alcohols. Show how to convert alcohols into other functional groups, like tosylates (TsOR), chlorides, bromides, or iodides. . Remember that these are all good substrates for substitution and elimination reactions. Reaction of tertiary (or allylic/benzylic) or secondary alcohols with the haloacids (HCl, HBr or HI) gives tertiary halides (S N 1). With secondary alcohols, rearrangements are possible if a more stable cations can form by a hydride shift. Primary and secondary alcohols react best with thionyl chloride or phosphorus tribromide (S N 2) to give the corresponding halide. For chiral secondary alcohols, SOCl 2 give retention of configuration while PBr 3 gives complete inversion of configuration. Tosylates are good leaving groups for both elimination and substitution reactions. Recognize when to use the following reagents, Ts-Cl/pyridine,
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