Creating and separating acetone
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- Creating and separating acetone
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Creating and separating acetone
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[post_content] => Practice Passage (Question 1-5)
*This passage is the property of Khan Academy and has been reformatted into an AAMC-style interface in their entirety by MedLife Mastery. MedLife Mastery does not endorse and is not an affiliate of Khan Academy.
Acetone is the active ingredient in nail polish remover and is ubiquitous in chemistry laboratories. Most laboratories order acetone in bulk not only for cleaning glassware, but also for use as a chemical reagent. One method for producing acetone is shown below
Figure 1. Creating acetone using benzene and propene as reactants.
Acetone can also be produced from the decarboxylation of acetoacetic acid. At temperatures above 0°C, acetoacetic acid spontaneously decomposes as shown in the following reaction
.
Figure 2. Creating acetone through decarboxylation of acetoacetic acid.
To isolate the products of these reactions, different techniques for separation and purification were utilized. The boiling points of some of these chemicals along with other common reagents are shown in the following table.
Table 1. A compilation of the boiling points of common chemicals in a laboratory.
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[question] => When distilling a mixture of benzene, acetone, phenol, and naphthalene, which compound would be distilled first?
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[description] => Reason for the Correct Answer:
Distillation separates compounds based on their boiling points.
Compounds with the lowest boiling point are distilled first.
Acetone has the lowest boiling point out of these four compounds; hence, it would be distilled first.
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[answers] => Array
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[0] => Array
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[each_answer] => A.naphthalene
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[each_answer] => B.phenol
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[each_answer] => C.acetone
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[each_answer] => D.benzene
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[question] => Which of the following pairs of chemicals could be best separated using simple distillation?
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[answer] => 4
[description] => Reason for the Correct Answer:
Distillation separates compounds based on their boiling points.
Simple distillation most effectively separates compounds that have a boiling point difference greater than 30 °C.
Most of these pairs of compounds have boiling points that are very close to each other. However, since formic acid has a boiling point of 101 °C and acetone has a boiling point of 56 °C, these can be readily separated through simple distillation.
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[each_answer] => A.benzene and hexane
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[each_answer] => B.acetone and hexane
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[each_answer] => C.dichloromethane and acetone
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[each_answer] => D.acetone and formic acid
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[question] => Which technique would be the most appropriate for separating acetone from hexane?
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[answer] => 3
[description] => Reason for the Correct Answer:
Column chromatography and thin layer chromatography separate compounds based on polarity.
Since acetone and hexane do not have a large difference in polarity, chromatography also would not be the best separation technique.
Distillation separates compounds based on their boiling points.
Simple distillation works best when the difference in boiling point between compounds is greater than 30 °C.
Since acetone and hexane have boiling points that are less than 30 °C, it would be appropriate to do fractional distillation instead of simple distillation.
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[each_answer] => A.thin layer chromatography
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[each_answer] => B.simple distillation
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[each_answer] => C.fractional distillation
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[each_answer] => D.column chromatography
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[question] => Benzene, phenol, acetoacetic acid, and ethanamine are all mixed together in a separatory funnel. If hydrochloric acid is added, which of these chemicals would be protonated?
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[answer] => 4
[description] => Reason for the Correct Answer:
Remember that acids protonate bases.
Amines are basic.
Ethanamine is the only basic compound out of these four, so it would be protonated by hydrochloric acid.
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[each_answer] => A.phenol
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[each_answer] => B.benzene
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[each_answer] => C.acetoacetic acid
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[question] => Which technique is most appropriate for separating two compounds so that the purified compound can be used in a subsequent reaction?
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[description] => Reason for the Correct Answer:
With gas chromatography, the sample is vaporized and cannot be recovered.
Paper chromatography is not a preparative technique.
Although thin layer chromatography can be done on a preparative scale, it is more commonly used as an analytical technique with very small samples of your reaction mixture.
Column chromatography is the best technique for separating compounds as part of a multistep synthesis.
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