The Grignard Synthesis of Triphenylmethanol Organic Chemistry Lab II March 19‚ 2012 Abstract The purpose of this experiment was to synthesize the Grignard reagent‚ phenyl magnesium bromide‚ and then use the manufactured Grignard reagent to synthesize the alcohol‚ triphenylmethanol‚ by reacting with benzophenone and protonation by H3O+. The triphenylmethanol was purified by recrystallization. The melting point‚ Infrared Spectroscopy‚ 13C NMR‚ and 1H NMR were used to characterize and confirm
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Grignard Synthesis of Triphenylmethanol from Benzophenone Purpose: The purpose of this experiment was to synthesize the tertiary alcohol triphenylmethanol from a Grignard reagent‚ phenyl magnesium bromide. The Grignard reagent was synthesized from bromobenzene and magnesium and then reacted with benzophenone to produce triphenylmethanol. It was important that water be excluded from the reaction‚ in order to prevent the formation of benzene. The reaction of phenyl magnesium bromide and benzophenone
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Abstract: The objective of the experiment was to prepare Benzilic acid by multistep synthesis starting with benzaldehyde. In this setup however‚ product of the first step‚ Benzoin‚ is provided thereby omitting the first step involving the conversion of benzaldehyde. For this experiment‚ the microscale techniques of reflux‚ crystallization‚ and melting-point determination were used. Utilizing these techniques a product yield of 93% for benzil and 57% for Benzilic acid was obtained‚ as well as
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Benzil is produced in the first step of this experiment’s multistep synthesis through the oxidation of benzoin. In order to produce the desired o-diketone‚ the alcohol on benzoin must be oxidized. Nitric acid was the oxidizing agent used in this experiment. As a result‚ the alcohol group on benzoin acted as the nucleophile and attacked the electrophilic nitrogen of nitric acid. As this step forms oxonium‚ excess water in the system deprotonated the oxonium to restore the neutral charge on oxygen
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The purpose of this experiment was to synthesize triphenylmethanol from a Grignard reagent. The Grignard reaction technique was used in this synthesis but due to the fact that it is such a strong nucleophile and base‚ it was important to prevent water from interfering with the Grignard reaction. Purity of the product was determined by measuring the melting point. Reagent Table: Structure Name Molecular formula Molar mass Density Melting point Boiling Point Diethyl ether C4H10O
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Lab #5: Grignard Reaction – Synthesis of Triphenylmethanol John Kang Chem 152L Performed: 7/20/04 Date submitted: ________________ Lab Partners: Sang Lee‚ Vicky Lai TA: John Stanko Abstract: This experiment explored the synthesis of triphenylmethanol through the use of Grignard reagents. The percent yield of the product was 10% on a relatively humid day. The melting point was calculate to be 127.2oC with a literature value of 162oC. An IR spectrum of the product was taken and used
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in the formation of triphenylmethanol from phenyl magnesium bromide and benzophenone. A recrystallization was performed to purify the Grignard product by dissolving the product in methanol. From here‚ a melting point range of 147.0 °C to 150.8 °C was obtained. The purified product yielded an IR spectrum with major peaks of 3471.82 cm-1‚ 3060.90 cm-1‚ 1597.38 cm-1‚ and 1489.64 cm-1‚ which helped to testify whether the identity of the product matched the expected triphenylmethanol. The identity of the
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Grignard Reaction: Synthesis of Triphenylmethanol Hai Liu TA: Ara Austin Mondays: 11:30-2:20 Abstract: In this experiment‚ phenylmagnesium bromide‚ a Grignard reagent was synthesized from bromobenzene and magnesium strips in a diethyl ether solvent. The Grignard reagent was then converted to triphenylmethanol‚ a tertiary alcohol with HCl. The reaction for phenylmagnesium bromide was: The reaction for Grignard to triphenylmethanol was: In the formation of the Grignard reagent
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phenylmagnesium bromide‚ a Grignard reagent‚ and react it with benzophenone to give triphenylmethanol. Once made‚ the Grignard reagent will do a nucleophilic attack on the carbonyl carbon of the ketone‚ benzophenone. The result is an alkoxide that is then protonated to give the alcohol‚ triphenylmethanol. The purity of the final product will then be considered by melting point and IR spectroscopy. Final purified triphenylmethanol weighed 8.02 grams and melted at 158.5-162 degrees Celsius. Introduction:
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Procedure: The experimental laboratory procedures were divided into two categories. First the formation of phenylmagnesium bromide‚ and second the reaction of the phenylmagnesium bromide with the carbonyl compound. However‚ before any of this could be done‚ the refluxing apparatus for the Grignard reaction was to be flame dried until no moisture remained inside because any water would cause the reagent to decompose and an alkane to form. The reaction would subsequently fail. Drierite was placed
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