grignardbenzoicacid(sonication)

grignardbenzoicacid(sonication) - GrignardReagent/Reactions

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Grignard Reagent / Reactions References: Pavia - p. 303 – 309; 313 314 Schornick http://classweb.gmu.edu/jschorni/chem318 11/15/10 1 Preparation of a Grignard Reagent  (Phenylmagnesiumbromide) and reaction with  Carbon Dioxide to form Benzoic Acid  through an Electrophilic Addition reaction
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Grignard Reagent / Reactions Synthesis of Benzoic Acid – Electrophilic Addition reaction  between a freshly prepared Grignard Reagent  (Organomagnesium Halide) acting as the Nucleophilie (Lewis  Base) and the Carbonyl group of Carbon Dioxide acting as the  positively charged Electrophile The Grignard Reagent must be prepared and reacted with the  solid Carbon Dioxide before the end of the day Sonication of mixture of Magnesium, Bromobenzene &  Ether (Ether acts as solvent and Grignard stabilizer) Reaction between Grignard Reagent and Carbon Dioxide Hydrolysis of Acid Salt Product Separation– Liquid/Liquid Extraction Precipitation Vacuum Filtration Product Purification – Recrystallization Product Verification – Melting Point 11/15/10 2
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Grignard Reagent / Reactions Laboratory Report : Synthesis Experiment Mass, Moles, Molar Ratio, Limiting Reagent,  Theoretical Yield Procedures Title – Concise: Simple Distillation, Dry Sample, IR  Spectrum, etc. Materials & Equipment (2 Columns in list (bullet)  form)           Note: include all reagents & principal equipment  used Description: Descriptions must be detailed, but concise 11/15/10 3
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Grignard Reagent / Reactions Laboratory Report : (Con’t) Results – Neat, logically designed template to present  results Summary Paragraph summarizing experimental observations,  computed results, and principal absorptions from IR &  NMR Analysis & Conclusions Limiting reagent Discuss the reaction in context with the results you  obtained; what evidence do you have to indicate you  got the intended product? Yield – How could the experimental process be  improved? 11/15/10 4
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Grignard Reagent / Reactions Background : Grignard Reagents, aka, Organomagnesium Halides Prepared by Reaction of an Organic Halide and  Magnesium metal turnings, usually in an Ether solvent  Relative Reactivity of Halides is important RI  >  RBr >  RCl  >  RF Very few Organomagnesium Fluorides are produced. Aryl Grignards are more easily prepared from Aryl  Bromides and Aryl Iodides than Aryl Chlorides Grignard Reagents are seldom isolated, but they can  be stabilized briefly in Ether solution and then used in  the preparation of other compounds The preparation of a Grignard Reagent usually  11/15/10 5
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δ δ δ δ δ δ δ δ δ + δ + δ + δ + Grignard Reagent / Reactions Reactions: 11/15/10 6
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This note was uploaded on 11/14/2010 for the course CHEM CHEM266L taught by Professor Christine during the Fall '10 term at Waterloo.

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grignardbenzoicacid(sonication) - GrignardReagent/Reactions

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