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2 - Organic Chemistry 6th Edition L G Wade Jr Chapter 11...

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Chapter 11 Reactions of Alcohols Jung-Mo Ahn Organic Chemistry , 6 th Edition L. G. Wade, Jr.
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Alcohol as Nucleophile ROH is weak nucleophile . But, the conjugate base (RO - ) is strong nucleophile . Williamson ether synthesis –1 ° R-X preferred R O H Na R O - + Na R' X R O R'
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Alcohol as an Electrophile •O H - is NOT a good leaving group – Unless it is protonated. – But, most nucleophiles are strong bases which would remove H + . Nuc O H Nuc O H H Nuc Nuc OH H 2 O Nuc H O H X
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Formation of Tosylate Ester p -toluenesulfonyl chloride Ts-Cl, “ Tosyl Chloride C O H CH 3 S Cl O O N 3 SO O O H C 3 S O O O C R-OTs, Tosylate Ester Tosylate – Good leaving group -C l -
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Reactions with Tosylates TsO - : Good leaving group
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Reduction of Alcohols No direct method Dehydrate with conc. H 2 SO 4 , then add H 2 Tosylate, then reduce with LiAlH 4 CH 3 CHCH 3 OH H 2 SO 4 2 CHCH 3 H 2 Pt 3 2 3 alcohol alkene alkane alcohol 3 CHCH 3 TsCl 3 3 OTs LiAlH 4 alkane 3 2 3 tosylate
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Reaction with HBr
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2 - Organic Chemistry 6th Edition L G Wade Jr Chapter 11...

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