Lab 9 - Experiment #9: Synthesis of Benzoic Acid: Grignard...

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CHEM 237 Lab Fall 2009 Objective The purpose of this experiment is to synthesize a Grignard reagent (phenylmagnesium bromide) and conduct a Grignard reaction by adding the nucleophilic reagent to the electrophilic carbon dioxide to produce benzoic acid. 5 Reagents Phenyl bromide CO 2 Iodine (I 2 ) Conc. HCl 10 10% aqueous NaOH Theory Grignard reagent is one of the most frequently used nucelophiles to generate C—C bond in organic synthesis. The Grignard reagent can be readily generated by reaction of organic halide with magnesium metal in organic solvent (Scheme 1). The Grinard reagent can react with a wide variety of electrophiles including ketones, aldehydes, esters, and epoxides. 15 RM g B r RX i) E + R E + MgBrOH ii) H 2 O Mg ether Scheme 1. Addition reaction of Grignard reagent R = alkyl vinyl phenyl (aryl) X = Br, Cl, or I Grignard reagent E + = ketone, aldehyde, ester, epoxide 20 25 In this experiment, phenylmagnesium bromide will be generated via the reaction of bromobenzene (phenylbromide) with magnesium. The reaction will be conducted by adding a solution of bromobenzene in dry ether to magnesium (activated by I 2 ). The formed
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Lab 9 - Experiment #9: Synthesis of Benzoic Acid: Grignard...

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