Sn1 Synthesis Essay

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SN1 Reaction Synthesis of Trityl Methyl Ether Introduction: In this experiment, a tertiary alcohol undergoes a substitution nucleophilic reaction; SN1 to form an ether. Trityl methyl ether will be synthesized from the reaction of triphenylmethanol (30 alcohol) and methanol. Triphenylmethanol can undergo this reaction because of the ease with which it dissociates to form a stable triphenylmethyl carbocation. From the structure of triphenylmethanol, it is observed that hydroxide is a poor leaving group. Due to this, the reaction takes place in acidic conditions by adding concentrated sulfuric acid to the solution. The sulfuric acid protonates the alcohol group in triphenylmethanol. The ether is formed when the carbocation reacts with methanol to form trityl methyl ether. H3O + + CH3OH Triphenylmethanol Trityl Methyl Ether Procedure: Approximately 0.1g of triphenylmethanol crystals was placed into a reaction tube and grinded to fine powder with a glass rod. 1ml of concentrated H2SO4 was then added to the tube and the solution was continuously stirred to dissolve all the triphenylmethanol. Using a Pasteur pipette, the sulfuric acid solution was then transferred to 2ml of ice cold methanol. Crystallization was induced by scratching the tube with a glass rod. The crystals were collected by vacuum filtration on a Hirsch funnel. After filtration, the crystals collected were washed thoroughly with water and then dried with filter paper. The weight of the crude material was determined and percentage yield was calculated. The melting point of the sample was also determined. The crude material was recrystallized from boiling methanol and the melting point of the purified Trityl methyl ether was measured. Results: 0.03g of the crude material was collected after initial filtration. Weight of
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