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10-AlcoholsF07HLS

10-AlcoholsF07HLS - Reactions of Alcohols 1 Dehydration...

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1 Reactions of Alcohols 1. Dehydration OH H 2 SO 4 or H 3 PO 4 conc . + H 2 O A. Mechanism All steps reversible! How to favor product? Rearrangements expected? 2. ROH to RX A) HX ROH + HX RX + H 2 O 1 o 2 o 3 o HCl HBr HI Example: OH HBr 90% Br + H 2 O Mechanism : 2. ROH to RX B) via sulfonate ester Example: Mechanism : ROTs + X RX + TsO OTs NaI DMSO I TsO Preparation: ROH + H 3 C S O O Cl N pyridine (py) tosyl chloride p-toluenesulfonylchloride TsCl
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2 Other sulfonate ester derivatives - what is similar, what is different? H 3 C S O O O H O S O O O CH 3 H 3 C H 3 C S O O O H H 3 C S O O Cl H 3 C S O O Cl O S O O CH 3 O S O O In which molecules is: •H most prone to attack by nucleophiles/bases (STRONG organic acids) •C most prone to attack by nucleophiles •S most prone to attack by nucleophiles Which of the following conditions would lead to the highest yield of the alkyl bromide shown below? OH HBr Br OH 1. TsCl, py 2. NaBr 2. ROH to RX C) With thionyl chloride, SOCl 2 Mechanism : HO R SOCl 2 pyridine *best with 1 o
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