Organic Lab report experiment mini lab 17

Organic Lab report experiment mini lab 17 - To Bri Simms...

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Unformatted text preview: To: Bri Simms, Section 3 From: Erica Chiadika Date: October 23, 2016 Subject: Experiment Mini Lab 17: An SNl Reaction of Bromotriphenylmethane Partner: No lab Partners Introduction: In this experiment bromotriphenylrnethane and ethanol is heated to form an ether, ethoxyn'iphenylmethane, by an SNl reaction. In the reaction, the bromine leaves the bromohiphenylrnetliane stable which makes the carbon a carbocation. Next the carbocation experiences a nucleophilic attack by the lone pairs that are on the oxygen. Aftcr that the hydrogen on the oxygen undergoes a proton transfer, and moves to the bromine. Ph M 1 ——-c— Br + HOACHB —:- Ph C+ —-- V Ph Ph Ph ‘ Ph— — — CH2CH3 + HB P11 (3+ 0 —CH2<:H3 C O r P11 ‘ H 13V P11 To: Bri Simms, Section 3 From: Erica Chiadika Date: October 23, 2016 Subject: Experiment Mini Lab 17: An SNl Reaction of Bromotriphenylmethane Partner: No lah Partners —Il‘l_-_ Bromotfi-hen methane —— Absolute Ethanol —— -—-—— Filter Pa -er with uroduct _— 70.9-73.5 de.rees Celsius Observations/Data: 0.50g of bromotriphenylmethane and 5.0mL of absolute ethanol was put into a test tube. When the absolute ethanol was added the mixture it turned clear, but as the ethanol dissolved it turned dark yellow. The test tube was held in a hot bath until no more HBr was evolved. A litmus paper was used to periodically test it while it was in the hot bath. Once the litmus paper stopped turning from blue to red, meaning no more HBr was present, the test tube was removed from the hot bath and allowed to cool to room temperature. After it reached room temperature it was put into an ice water bath to further cool. While it was in the ice bath the inside of the test tube was scratched with a stirring rod to induce crystallization. After that the ethoxytriphenvlmethane in the test tube was collected and dried on a sheet of filter paper by vacuum filtration. The product was then weighed, and the starting and ending melting point of the product was taken was taken. Resultsmiscussion: Absolute ethanol was added to the mixture five times but the HBr was still present. The fiflzh time it was added, the solution was not tested with litmus paper, but instead allowed to cool to room temperature. The product also had little crystallization. This could cause my results to be skewed, resulting in a high percent yield, and, less product. Calculations: The melting temperature of ethoxytriphenylmethane is 73 degrees Celsius. So the melting point of the product should be around 73 degrees Celsius. I Melting point range: Beginning: 70.9 To: Bri Simms, Section 3 From: Erica Chiadika Date: October 23, 2016 Subject: Experiment Mini Lab 17: An SNl Reaction of Bromotriphenylmethane Partner: No lab Partners Ending:73.5 I Theoretical yield of bromotriphenylmethane: 1.50 mmol of bromoiriphenylrnethane x (1 mol of bromotriphenylrnethanef 1000 mmol of bromon'iphenylrnethane) x (1 mol ethoxyh‘iphenylmethanef lmol of bromolriphenylrnethane) x (.41g of ethoxyfliphenylmethanef lmol ethoxytriphenylmethane) = .00061 5 g of ethoxytriphenylmethane I Percent yield: (.057g of ethoxytr‘iphenylmethanefi001476g of ethoxytriphenylmethane) X 100 = 38.62% Experimental: : 0.50g of bromotriphenvlmethane and 5.0mL of absolute ethanol was put into a test tube. The test tube was held in a hot bath until no more HBr was evolved. A litmus paper was used to periodically test it while it was in the hot bath. Once the litmus paper stopped turning from blue to red, meaning no more HBr was present, the test tube was removed from the hot bath and allowed to cool to room temperature. After it reached room temperature it was put into an ice water bath to further cool. While it was in the ice bath the inside of the test tube was scratched with a stirring rod to induce crystallization. After that the ethoxytriphenylmethane in the test tube was collected and dried on a sheet of filter paper by vacuum filtration. The product was then weighed, and the starting and ending melting point of the product was taken was taken. References : (1) Lehman, J. W. Operational Organic Chemistry; A Problem-Solving Approach to the laboratory Course, cl”1 Ed.; Pearson Prentice Hall, 2009; pp 499-500 ...
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