•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?

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11:34
Procedure: Caution: do not change the order of addition given here.
• want for Togo
11-7
LTE
x15
g.
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 ml
concentrated HC1 (37% HCl density-1.18 g/ml,,
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.
11.7
g
74.12
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.
Waste:
1.
water
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.
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"
X
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 SN2 reactions with alcohols also take place at neutral or basic pH?
x
Transcribed Image Text:11:34 Procedure: Caution: do not change the order of addition given here. • want for Togo 11-7 LTE x15 g. 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 ml concentrated HC1 (37% HCl density-1.18 g/ml,, 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. 11.7 g 74.12 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. Waste: 1. water 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. 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" X 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 SN2 reactions with alcohols also take place at neutral or basic pH? x
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