Organic Chemistry I LAB EXAM: FINAL BROMINATION OF BENZENE SYNTHESIS AND PURIFICATION OF BROMOBENZENE: PROCEDURE DATA TABLE Chemical Boiling point C Melting Point C Density g/mL Solubility Benzene 80.1 5.5 0.88 Slightly in H2O Toluene 110.6 -93 0.87 Slightly in H2O Bromobenzene 155-156 -30.8 1.50 Insoluble Dibromobenzene 220.40 87.31 0.96 Insoluble MATERIALS: Graduated cylinder Weight scale Buchner funnel Filter flask Rubber stopper Hot plate Thermometer Conical funnel Various
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Grignard reagent (phenylmagnesium bromide) was performed from a bromobenzene reactant combined with magnesium and ether. Phenylmagnesium bromide was then transformed into a tertiary alcohol called triphenylmethanol‚ through addition of another compound called benzophenone‚ as well as additional ether. The end product of triphenylmethanol was analyzed via NMR and IR. Figure 1: Preparation of the Grignard agent by combining bromobenzene with magnesium and ether to produce phenylmagnesium bromide. Figure
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Objective: The goal of this lab is to synthesize a Grignard reagent from bromobenzene and magnesium metal in diethyl ether. This same Grignard reagent would then be used to prepare a tertiary alcohol and then purify and characterize the product. Table of Reagents: Name Chemical formula Melting Point Boiling Point Density Safety Hazards Diethyl ether C4H10O -116.3°C 34.6°C 0.7134 g/ml Flammable Bromobenzene C6H5Br -30.6°C 156°C 1.5 g/ml Irritant. Avoid contact with skin‚
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References: 1. Chem 152 lab manual. Blackboard. http://courses.duke.edu. 2. ICSC 1016 BROMOBENZENE. http://www.ilo.org/public/english/protection/safework/cis/products/icsc/dtasht/_icsc10/icsc1016.htm. Date visited: 7/27/2004. 3. Organic Chemistry‚ 4th Ed. Loudon.
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Abstract: The purpose of this lab was to synthesize triphenylmethanol from benzophenone and bromobenzene by the formation of a Grignard compound with the reagents bromobenzene and magnesium metal. The bromobenzene was first transformed into the Grignard compound and was then reacted with the benzophenone to make the final product. The mixture was then mixed with sulfuric acid and the organic layer was extracted via a separatory funnel. The mixture was then recrystallized from methanol and was allowed
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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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Preparation Of Triphenylmethanol Objectives 1. To study the preparation of triphenylmethanol using through Gridnard reaction 2. To study the operations of anhydrous reaction‚ water vapor distillation. Principles Alcohol is widely used in organic chemistry‚ not only as solute but also as intermediate to synthesize halide‚ alkene‚ ether‚ aldehyde and ketone etc. In laboratory‚ an important method of synthesizing alcohol is though the addition reaction of Gridnard reagent and carbonyl compound‚ whereas
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Flammable‚ irritant 2-chloro-2-methylpropane 92.57 51 -26 0.89 Flammable‚ irritant acetone 58.08 56.5 -95 0.793 flammable Crotyl Chloride 90.55 73 -65 0.923 Flammable‚ irritant Benzyl Chloride 126.59 179 -43 1.211 Flammable‚ irritant Bromobenzene 157.02 156 -31 1.491 Flammable‚ irritant bromocyclohexane 163.10 167 -57 1.324 Irritant‚ flammable Bromocyclopentane 149.03 138 -95 1.390 Irritant‚ flammable 1-chlorobutane 92.58 78 -123 0.881 Irritant‚ Flammable 2-chlorobutane 92
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stretches including differences in both spectra. Results | | Amounts and units | |Initial volume of bromobenzene | | |Initial weight of bromobenzene (g) | | |Initial weight of magnesium (g) | | |Initial weight of benzophenone (g)
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melting point. Reagent Table: Structure Name Molecular formula Molar mass Density Melting point Boiling Point Diethyl ether C4H10O 74.12 g mol− 0.7134 g/cm3‚ liquid -116.3 °C‚ 157 K‚ -177 °F 34.6 °C‚ 308 K‚ 94 °F Bromobenzene C6H5Br 157.01 g mol−1 1.495 g/cm³‚ liquid -30.8 °C (242.35 K) 156 °C (429.15 K) Phenylmagnesium bromide C6H5MgBr 181.31 g/mol 1.14
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