10and11AlcoholsEthersExpodesF07

10and11AlcoholsEthersExpodesF07 - Reactions of Alcohols 1...

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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?
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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 :
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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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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
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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
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2. ROH to RX C) With thionyl chloride, SOCl 2 Mechanism : HO R SOCl 2 pyridine *best with 1 o ROH Advantage OH S O Cl Cl O H S Cl O (152) + Cl N
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Similarly: D) Phosphorous bromide, PBr 3 OH PBr 3 0 o C Br + P(OH) 3 H 3 PO 3
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3. Oxidation Oxidation: Reduction: C H H H H C H H OH H C H O H C H O OH 0 1 2 3 C H R OH H C R O H Aldehyde Ketone C R O OH Carboxylic Acid C R R OH H C R O R C R R OH R Oxidizing Agent Oxidizing Agent Oxidizing Agent OR
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