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Last summer lab report

Last summer lab report - Experiment 7 Preparation of Methyl...

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Experiment 7: Preparation of Methyl Benzoate and its Reaction with Phenyl Grignard Discussion: The purpose of this lab was to prepare triphenylmethanol in a three-day experiment. Sulfuric acid (strong acid) was required to initiate the reaction and protonate the carboxylic acid of the starting material (benzoic acid). Then, methanol was used to attack the alpha carbon. The removal of H 2 O yields the formation of the ester (methyl benzoate). This reaction is called Fischer Esterification and is shown below in figure.1. Afterwards, the Grignard reagent (phenylmagneisum bromide) is formed by reacting an alkyle or aryl halide (the bromobezene) with magnesium as shown in figure.2. Phenyl Grignard reagent is used to form two new carbon- carbon bonds for methyl benzoate which produced magnesium salt of a tertiary alcohol. Sulfuric acid was then used to hydrolyze the salt and produce an inorganic magnesium salt and the tertiary alcohol (triphenylmethanol) as a final product as indicated in the reaction scheme shown in figure.4 . During the first day, benzoic acid was mixed with methanol and was refluxed with sulphuric acid. The solution was transferred into a separatory funnel containing water and the aqueous layer was drained off while the product was extracted in the ethereal layer. The ethereal phase was washed with sodium bicarbonate to remove any unreacted benzoic acid and was then filtered. The ether was then evaporated using a stream bath. The final product of this day was
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