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CHEM261 (5)

Organic Chemistry Reactions

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David Bundle

ACID CATALYZED DEHYDRATION OF ALCOHOLS y Alcohols can be dehydrated to give alkenes and the reverse reaction hydration of alkenes can be used to synthesize alcohols y Dehydration works best with tertiary then secondary and then primary y Alcohol is treated with a strong acid phosphoric HPOor sulfuric HSO 34 24y Primary Alcohols o E2 mechanism o The acid catalyst protonates the OH group creating a protonated alcohol and water can then be a good leaving group when a water molecule or alcohol acts as a base and abstracts a beta proton y Secondary or Tertiary Alcohols o E1 mechanism o The alcohol is first protonated and water then acts as a good leaving group in a slow ratedetermining step to create a carbocation o Then water or alcohol acts as a base to remove a beta hydrogenDEHYDROHALOGENATION y Synthesis of Alkenes from Alkanes o E2 mechanism o Secondary or tertiary alkyl halides o Alkoxide bases such as sodium ethoxide or potassium tertbutoxide o Zaitsevs Rule Formation of the most substituted alkene is favored with a
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