11:34Procedure: Caution: do not change the order of addition given here.• want for Togo11-7LTEx15g.Using a graduated cylinder, place 15 ml t-butyl alcohol (density = 0.78 g/ml,moles) in a 250 mL Er flask. Working under the hood, slowly add 37 mlconcentrated HC1 (37% HCl density-1.18 g/ml,,moles) in portions withswirling. The insoluble t-butyl chloride will rise to the top of the aqueous layer as it is formed. /4.61Periodically swirl the flask for about five minutes to insure complete reaction of any alcoholremaining partly dissolved in the t-butyl chloride layer and out of contact with the aqueous acid.11.7g74.12After five minutes, carefully transfer the contents of the flask into a separatory funnel andallow the phases to separate completely. Remove and discard the aqueous layer (after you havechecked to make sure it is aqueous layer). Wash the organic layer by adding 30ml water to theseparatory funnel, mixing, allowing the layers to separate, and removing the aqueous layer again.Now remove traces of acid by placing the organic layer in a 400ml beaker and carefullyadding 30 mL sodium bicarbonate solution. The solution will bubble as the bicarbonate reactswith any remaining acid to produce carbon dioxide.Waste:1.waterReturn the contents of the beaker to the separatory funnel and remove the aqueous layer.Now wash the organic layer with 30ml water to remove any traces of base. Drain the aqueouslayer and then pour the organic layer through the mouth of the funnel into a dry Erlenmeyerflask. Add about a half teaspoon of the drying agent, anhydrous calcium chloride, to the flaskand let it stand with frequent swirling for about five minutes.2.Assemble a simple distillation apparatus. Note: All pieces must be dry. Decant the driedt-butyl chloride into a dry 50 ml round bottomed flask, add two boiling stones and distill slowlywith a low flame. Collect the distillate boiling at 48-52°C in a pre-weighed bottle placed in anice water bath, Weigh your final product, determine the %purity by GC, and calculate thepercent yield.)•Set temp. at 80cPlace Aqueous layer into a beaker labeled "Aqueous Layer"Place product into beaker labeled "t-Butyl Chloride"XQuestions1. Your product, t-butyl chloride, is also tertiary and has a good leaving group. Why doesn'tit also ionize and continue to react?2. Why can't Syl and SN2 reactions with alcohols also take place at neutral or basic pH?x

SN1: SN1stands for substitution nucleophilic unimolecular. SN1 reactions occurs by formation of…

•want top Procedure: Caution: do not change the order of addition given here. x15 Using a graduated cylinder, place 15 ml t-butyl alcohol (density -0.78 g/ml, moles) in a 250 mL-Erfask. Working under the hood, slowly add 37 ml concentrated HC1 (37% HCI density-1.18 g/ml,, 74.12 moles) in portions with swirling. The insoluble t-butyl chloride will rise to the top of the aqueous layer as it is formed. /4,61 Periodically swirl the flask for about five minutes to insure complete reaction of any alcohol remaining partly dissolved in the t-butyl chloride layer and out of contact with the aqueous acid. 8. 11.7 8. 11.-7 After five minutes, carefully transfer the contents of the flask into a separatory funnel and allow the phases to separate completely. Remove and discard the aqueous layer (after you have checked to make sure it is aqueous layer). Wash the organic layer by adding 30ml water to the separatory funnel, mixing, allowing the layers to separate, and removing the aqueous layer again. Now remove traces of acid by placing the organic layer in a 400ml beaker and carefully adding 30 mL sodium bicarbonate solution. The solution will bubble as the bicarbonate reacts with any remaining acid to produce carbon dioxide. Return the contents of the beaker to the separatory funnel and remove the aqueous layer. Now wash the organic layer with 30ml water to remove any traces of base. Drain the aqueous layer and then pour the organic layer through the mouth of the funnel into a dry Erlenmeyer flask. Add about a half teaspoon of the drying agent, anhydrous calcium chloride, to the flask and let it stand with frequent swirling for about five minutes. Waste: 1. 2. Assemble a simple distillation apparatus. Note: All pieces must be dry. Decant the dried t-butyl chloride into a dry 50 ml round bottomed flask, add two boiling stones and distill slowly with a low flame. Collect the distillate boiling at 48-52°C in a pre-weighed bottle placed in an ice water bath, Weigh your final product, determine the %purity by GC, and calculate the percent yield] •Set temp. at 80c Place Aqueous layer into a beaker labeled "Aqueous Layer" Place product into beaker labeled "t-Butyl Chloride" Questions 1. Your product, t-butyl chloride, is also tertiary and has a good leaving group. Why doesn't it also ionize and continue to react? 2. Why can't Syl and Sx2 reactions with alcohols also take place at neutral or basic pH?

•want top Procedure: Caution: do not change the order of addition given here. x15 Using a graduated cylinder, place 15 ml t-butyl alcohol (density -0.78 g/ml, moles) in a 250 mL-Erfask. Working under the hood, slowly add 37 ml concentrated HC1 (37% HCI density-1.18 g/ml,, 74.12 moles) in portions with swirling. The insoluble t-butyl chloride will rise to the top of the aqueous layer as it is formed. /4,61 Periodically swirl the flask for about five minutes to insure complete reaction of any alcohol remaining partly dissolved in the t-butyl chloride layer and out of contact with the aqueous acid. 8. 11.7 8. 11.-7 After five minutes, carefully transfer the contents of the flask into a separatory funnel and allow the phases to separate completely. Remove and discard the aqueous layer (after you have checked to make sure it is aqueous layer). Wash the organic layer by adding 30ml water to the separatory funnel, mixing, allowing the layers to separate, and removing the aqueous layer again. Now remove traces of acid by placing the organic layer in a 400ml beaker and carefully adding 30 mL sodium bicarbonate solution. The solution will bubble as the bicarbonate reacts with any remaining acid to produce carbon dioxide. Return the contents of the beaker to the separatory funnel and remove the aqueous layer. Now wash the organic layer with 30ml water to remove any traces of base. Drain the aqueous layer and then pour the organic layer through the mouth of the funnel into a dry Erlenmeyer flask. Add about a half teaspoon of the drying agent, anhydrous calcium chloride, to the flask and let it stand with frequent swirling for about five minutes. Waste: 1. 2. Assemble a simple distillation apparatus. Note: All pieces must be dry. Decant the dried t-butyl chloride into a dry 50 ml round bottomed flask, add two boiling stones and distill slowly with a low flame. Collect the distillate boiling at 48-52°C in a pre-weighed bottle placed in an ice water bath, Weigh your final product, determine the %purity by GC, and calculate the percent yield] •Set temp. at 80c Place Aqueous layer into a beaker labeled "Aqueous Layer" Place product into beaker labeled "t-Butyl Chloride" Questions 1. Your product, t-butyl chloride, is also tertiary and has a good leaving group. Why doesn't it also ionize and continue to react? 2. Why can't Syl and Sx2 reactions with alcohols also take place at neutral or basic pH?

Organic Chemistry

8th Edition

ISBN:9781305580350

Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote

Publisher:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote

Chapter20: Dienes, Conjugated Systems, And Pericyclic Reactions

Section: Chapter Questions

Problem 20.48P

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