Extraction

<img src="http://irtutor.com/media/SepFunnel_empty.jpg"><img src="http://irtutor.com/media/Vial_full.jpg"><img src="http://irtutor.com/media/Beaker_empty.jpg"> This is a simulation of the separation of a mixture of benzoic acid and naphthalene by liquid-liquid extraction. Record any data that is provided. You can repeat the experiment as many times as you wish, but each time you start at this page, a new set of data is generated. (set: $studentName = "Student") Please enter your name <input type="text" data-varname="studentName">\ <script>processInputElements();</script> What would you like to do to get started? [[weigh the sample + vial]] [[weigh an empty beaker]] [[pour solid into empty beaker]] Copyright (c) 2020 Charles Abrams cabrams@ccc.edu Permission is hereby granted for all adademic uses with attribution. No commercial uses are permitted. Created with Twinery.org (Harlowe) <!-- set up ALL variables here so we know this is the start/restart --!> <!-- we want a total of about 6 grams of solid mixture --!> <!-- "A" represents the acid (benzoic acid) and "N" represents the neutral compound (naphthalene). Later we can add B for a base --!> (set:$massA = (random:2,4)+(random:1,81)/100) (set:$massN = 6 - $massA + (random:1,45)/100) (set:$massVial = (random:6,7)+(random:1,86)/100) (set:$massBeaker = (random:67,75)+(random:1,95)/100) (set:$organicN = 0, $aqueousN = 0, $organicA = 0, $aqueousA = 0) (set:$aqphase = "") (set:$massPpt = 0, $massEvap = 0) (set:$moleFrac1 = 0, $moleFrac2 = 0) (set:$pctSolid1 = 0, $pctSolid2 = 0) <!--Set the volumes of liquid in the flasks to zero--!> <!--We won't let the user put more than one liquid into the flask, so it will not have both ether and water.--!> (set: $flask1 to (dm: "phase","none","volume",0,"A",0,"N",0,"done","no")) (set: $flask2 to (dm: "phase","none","volume",0,"A",0,"N",0,"done","no")) (set: $flask1Name = 0, $flask2Name = 0) <!--Set the partition constants for A and N. This is the equilibrium ratio ether/aqueous for each of the aqueous solutions --!> (set:$KpA to (dm: "NaOH", .1, "HCl", 1000, "NaCl", 1000)) (set:$KpN to (dm: "NaOH", 10000, "HCl", 10000, "NaCl", 10000))

<img src="http://irtutor.com/media/SepFunnel_empty.jpg"><img src="http://irtutor.com/media/Vial_empty.jpg"><img src="http://irtutor.com/media/Beaker_full.jpg"> 20 mL of diethyl ether was added to the beaker. All of the solid dissolved after stirring for a minute. <!-- the entire mass of each solid is now in the organic layer--!> (set:$organicN = $massN, $organicA = $massA) [[weigh the empty vial|after dissolving]] [[pour the ether solution into the separatory funnel]] [[Restart the experiment|Extraction Start]]

<img src="http://irtutor.com/media/SepFunnel_empty.jpg"><img src="http://irtutor.com/media/Vial_empty_balance.jpg"><img src="http://irtutor.com/media/Beaker_xtal.jpg"> You measure the mass of the empty vial on the analytical balance. The weight of the empty vial is (print:$massVial.toFixed(4)) grams [[add 20mL diethyl ether]] to the beaker

<img src="http://irtutor.com/media/SepFunnel_empty.jpg"><img src="http://irtutor.com/media/Vial_full.jpg"><img src="http://irtutor.com/media/Beaker_empty_balance.jpg"> The empty beaker is placed on the analytical balance. The mass of the empty beaker is (print:$massBeaker.toFixed(4)) grams You should write this down in your notebook just like a real lab experiment. [[weigh the sample + vial]] [[pour solid into empty beaker]]

<img src="http://irtutor.com/media/SepFunnel_empty.jpg"><img src="http://irtutor.com/media/Vial_empty.jpg"><img src="http://irtutor.com/media/Beaker_xtal.jpg"> You have added the solid mixture to an empty beaker [[weigh the beaker + sample]] [[weigh the empty vial]] [[add 20mL diethyl ether]] to the beaker

<img src="http://irtutor.com/media/SepFunnel_empty.jpg"><img src="http://irtutor.com/media/Vial_full_balance.jpg"><img src="http://irtutor.com/media/Beaker_empty.jpg"> The sample and vial are placed on an analytical balance. (set:$result = $massN + $massA + $massVial) The mass of the sample and vial is (print:$result.toFixed(4)) grams. Make sure you write down this information in your notebook! [[pour solid into empty beaker]] [[weigh an empty beaker]]

<img src="http://irtutor.com/media/SepFunnel_empty.jpg"><img src="http://irtutor.com/media/Vial_empty.jpg"><img src="http://irtutor.com/media/Beaker_xtal_balance.jpg"> (set: $result = $massBeaker + $massA + $massN) Your beaker plus sample weighs (print:$result.toFixed(2)) grams [[add 20mL diethyl ether]] to the beaker

<img src="http://irtutor.com/media/SepFunnel_half.jpg"> The solution was poured into the separatory funnel. It now contains an ether solution of the mixture of two substances. The vial and beaker are no longer needed. What do you want to add to the separatory funnel? [[add 10 mL 0.5 M NaOH]] [[add 10 mL 0.5 M HCl]] [[add 10 mL saturated NaCl]]

(set:_x1 = $flask1's "volume", _x2 = $flask2's "volume")<img src="http://irtutor.com/media/SepFunnel_full.jpg">(if:_x1 is 0)[<img src="http://irtutor.com/media/Flask1_empty.jpg">](else-if:_x1 is 10)[<img src="http://irtutor.com/media/Flask1_10ml.jpg">](else-if:_x1 is 20)[<img src="http://irtutor.com/media/Flask1_20ml.jpg">](else:)[<img src="http://irtutor.com/media/Flask1_30ml.jpg">](if:_x2 is 0)[<img src="http://irtutor.com/media/Flask2_empty.jpg">](else-if:_x2 is 10)[<img src="http://irtutor.com/media/Flask2_10ml.jpg">](else-if:_x2 is 20)[<img src="http://irtutor.com/media/Flask2_20ml.jpg">](else:)[<img src="http://irtutor.com/media/Flask2_30ml.jpg">] 10 mL 0.5 M NaOH was added to the separatory funnel. It was then stoppered, shaken and vented, and allowing to settle. The stopper was removed. [[test the upper layer to see if it is water or ether]] (if: _x1 < 30)[[[drain the lower layer into Flask 1|E1]] (if: $flask1Name is 0)[](else:)[($flask1Name)] ] (if: _x2 < 30)[[[drain the lower layer into Flask 2|E2]](if: $flask2Name is 0)[](else:)[($flask2Name)] ] <!-- Declare that this is base, in case student later adds acid--!> (set: $aqphase = "NaOH") <!-- Calculate the partition and put the amounts into the correct variables. The factor of 2 in the equations below comes from extracting 20 mL of ether with 10 ml of sodium hydroxide --!> <!-- First calculate the values for the acid --!> (set:_T = $organicA) (set: _K = $KpA's "NaOH") (set: _x = (_T * _K)/(2 + _K)) (set: $aqueousA = _T - _x) (set: $organicA = _x) <!-- Repeat the calculation for the neutral substance --!> (set: _T = $organicN) (set: _K = $KpN's "NaOH") (set: _x = (_T * _K)/(2 + _K)) (set: $aqueousN = _T -_x) (set: $organicN = _x)

(set:_x1 = $flask1's "volume", _x2 = $flask2's "volume")<img src="http://irtutor.com/media/SepFunnel_full.jpg">(if:_x1 is 0)[<img src="http://irtutor.com/media/Flask1_empty.jpg">](else-if:_x1 is 10)[<img src="http://irtutor.com/media/Flask1_10ml.jpg">](else-if:_x1 is 20)[<img src="http://irtutor.com/media/Flask1_20ml.jpg">](else:)[<img src="http://irtutor.com/media/Flask1_30ml.jpg">](if:_x2 is 0)[<img src="http://irtutor.com/media/Flask2_empty.jpg">](else-if:_x2 is 10)[<img src="http://irtutor.com/media/Flask2_10ml.jpg">](else-if:_x2 is 20)[<img src="http://irtutor.com/media/Flask2_20ml.jpg">](else:)[<img src="http://irtutor.com/media/Flask2_30ml.jpg">] 10 mL 0.5 M HCl was added to the separatory funnel. It was then stoppered, shaken and vented, and allowing to settle. The stopper was removed. [[test the upper layer to see if it is water or ether]] (if: _x1 < 30)[[[drain the lower layer into Flask 1|E1]]] (if: _x2 < 30)[[[drain the lower layer into Flask 2|E2]]] <!-- Declare that this is base, in case student later adds acid--!> (set: $aqphase = "HCl") <!-- Calculate the partition and put the amounts into the correct variables. The factor of 2 in the equations below comes from extracting 20 mL of ether with 10 ml of hydrochloric acid --!> <!-- First calculate the values for the acid --!> (set:_T = $organicA) (set: _K = $KpA's "HCl") (set: _x = (_T * _K)/(2 + _K)) (set: $aqueousA = _T - _x) (set: $organicA = _x) <!-- Repeat the calculation for the neutral substance --!> (set: _T = $organicN) (set: _K = $KpN's "HCl") (set: _x = (_T * _K)/(2 + _K)) (set: $aqueousN = _T -_x) (set: $organicN = _x)

(set:_x1 = $flask1's "volume", _x2 = $flask2's "volume")<img src="http://irtutor.com/media/SepFunnel_full.jpg">(if:_x1 is 0)[<img src="http://irtutor.com/media/Flask1_empty.jpg">](else-if:_x1 is 10)[<img src="http://irtutor.com/media/Flask1_10ml.jpg">](else-if:_x1 is 20)[<img src="http://irtutor.com/media/Flask1_20ml.jpg">](else:)[<img src="http://irtutor.com/media/Flask1_30ml.jpg">](if:_x2 is 0)[<img src="http://irtutor.com/media/Flask2_empty.jpg">](else-if:_x2 is 10)[<img src="http://irtutor.com/media/Flask2_10ml.jpg">](else-if:_x2 is 20)[<img src="http://irtutor.com/media/Flask2_20ml.jpg">](else:)[<img src="http://irtutor.com/media/Flask2_30ml.jpg">] 10 mL saturated NaCl was added to the separatory funnel. It was then stoppered, shaken and vented, and allowing to settle. The stopper was removed. [[test the upper layer to see if it is water or ether]] (if: _x1 < 30)[[[drain the lower layer into Flask 1|E1]]] (if: _x2 < 30)[[[drain the lower layer into Flask 2|E2]]] <!-- Declare that this is base, in case student later adds acid--!> (set: $aqphase = "NaCl") <!-- Calculate the partition and put the amounts into the correct variables. The factor of 2 in the equations below comes from extracting 20 mL of ether with 10 ml of sodium hydroxide --!> <!-- First calculate the values for the acid --!> (set:_T = $organicA) (set: _K = $KpA's "NaCl") (set: _x = (_T * _K)/(2 + _K)) (set: $aqueousA = _T - _x) (set: $organicA = _x) <!-- Repeat the calculation for the neutral substance --!> (set: _T = $organicN) (set: _K = $KpN's "NaCl") (set: _x = (_T * _K)/(2 + _K)) (set: $aqueousN = _T -_x) (set: $organicN = _x)

<img src="http://irtutor.com/media/SepFunnel_empty.jpg"><img src="http://irtutor.com/media/Vial_empty_balance.jpg"><img src="http://irtutor.com/media/Beaker_full.jpg"> The empty vial is placed on the analytical balance. The weight of the empty vial is (print:$massVial.toFixed(4)) grams [[pour the ether solution into the separatory funnel]]

(set: $flask1's "phase" to $aqphase, $flask1's "A" to it + $aqueousA, $flask1's "N" to it + $aqueousN, $flask1's "volume" to it + 10)(set:_x1 = $flask1's "volume", _x2 = $flask2's "volume") <img src="http://irtutor.com/media/SepFunnel_half.jpg">(if:_x1 is 0)[<img src="http://irtutor.com/media/Flask1_empty.jpg">](else-if:_x1 is 10)[<img src="http://irtutor.com/media/Flask1_10ml.jpg">](else-if:_x1 is 20)[<img src="http://irtutor.com/media/Flask1_20ml.jpg">](else:)[<img src="http://irtutor.com/media/Flask1_30ml.jpg">](if:_x2 is 0)[<img src="http://irtutor.com/media/Flask2_empty.jpg">](else-if:_x2 is 10)[<img src="http://irtutor.com/media/Flask2_10ml.jpg">](else-if:_x2 is 20)[<img src="http://irtutor.com/media/Flask2_20ml.jpg">](else:)[<img src="http://irtutor.com/media/Flask2_30ml.jpg">] The lower layer of from the separatory funnel was drained into Flask 1 (if: $flask1Name is 0)[Label Flask 1 (optional):<input type="text" data-varname="flask1Name">\ <script>processInputElements();</script> ](else:)[ ($flask1Name)] What do you want to do now? [[add 10 mL 0.5 M NaOH]] to the separatory funnel containing the upper layer [[add 10 mL 0.5 M HCl]] to the separatory funnel containing the upper layer [[add 10 mL saturated NaCl]] to the separatory funnel containing the upper layer (if: $flask1's "phase" is "none")[[[pour the upper layer into Flask 1|organicE1]]] (if: $flask2's "phase" is "none")[[[pour the upper layer into Flask 2|organicE2]]] [[Extraction Start]]

(set: $flask2's "phase" to $aqphase, $flask2's "A" to it + $aqueousA, $flask2's "N" to it + $aqueousN, $flask2's "volume" to it + 10)(set:_x1 = $flask1's "volume", _x2 = $flask2's "volume") <img src="http://irtutor.com/media/SepFunnel_half.jpg">(if:_x1 is 0)[<img src="http://irtutor.com/media/Flask1_empty.jpg">](else-if:_x1 is 10)[<img src="http://irtutor.com/media/Flask1_10ml.jpg">](else-if:_x1 is 20)[<img src="http://irtutor.com/media/Flask1_20ml.jpg">](else:)[<img src="http://irtutor.com/media/Flask1_30ml.jpg">](if:_x2 is 0)[<img src="http://irtutor.com/media/Flask2_empty.jpg">](else-if:_x2 is 10)[<img src="http://irtutor.com/media/Flask2_10ml.jpg">](else-if:_x2 is 20)[<img src="http://irtutor.com/media/Flask2_20ml.jpg">](else:)[<img src="http://irtutor.com/media/Flask2_30ml.jpg">] The lower layer of from the separatory funnel was drained into Flask 2 (if: $flask2Name is 0)[Label Flask 2 (optional):<input type="text" data-varname="flask2Name">\ <script>processInputElements();</script> ](else:)[ ($flask2Name)]. What do you want to do now? [[add 10 mL 0.5 M NaOH]] to the separatory funnel containing the upper layer [[add 10 mL 0.5 M HCl]] to the separatory funnel containing the upper layer [[add 10 mL saturated NaCl]] to the separatory funnel containing the upper layer (if: $flask1's "phase" is "none")[[[pour the upper layer into Flask 1|organicE1]]] (if: $flask2's "phase" is "none")[[[pour the upper layer into Flask 2|organicE2]]] [[Extraction Start]]

(set: $flask2's "phase" to "organic", $flask2's "A" to $organicA, $flask2's "N" to $organicN, $flask2's "volume" to it + 10)(set:_x1 = $flask1's "volume", _x2 = $flask2's "volume") <img src="http://irtutor.com/media/SepFunnel_empty.jpg">(if:_x1 is 0)[<img src="http://irtutor.com/media/Flask1_empty.jpg">](else-if:_x1 is 10)[<img src="http://irtutor.com/media/Flask1_10ml.jpg">](else-if:_x1 is 20)[<img src="http://irtutor.com/media/Flask1_20ml.jpg">](else:)[<img src="http://irtutor.com/media/Flask1_30ml.jpg">](if:_x2 is 0)[<img src="http://irtutor.com/media/Flask2_empty.jpg">](else-if:_x2 is 10)[<img src="http://irtutor.com/media/Flask2_10ml.jpg">](else-if:_x2 is 20)[<img src="http://irtutor.com/media/Flask2_20ml.jpg">](else:)[<img src="http://irtutor.com/media/Flask2_30ml.jpg">] The upper layer was poured into flask 2 (if: $flask2Name is 0)[Label Flask 2 (optional):<input type="text" data-varname="flask2Name">\ <script>processInputElements();</script> ](else:)[ ($flask2Name)] [[add drying agent to flask 1|dry E1]] [[add drying agent to flask 2|dry E2]] <!-- later, add back extraction of E1 or E2 with saturated NaCl--!> [[add acid dropwise to flask 1]] [[add acid dropwise to flask 2]] [[add base dropwise to flask 1]] [[add base dropwise to flask 2]] [[Extraction Start]]

(set: $flask1's "phase" to "organic", $flask1's "A" to $organicA, $flask1's "N" to $organicN, $flask1's "volume" to it + 10)(set:_x1 = $flask1's "volume", _x2 = $flask2's "volume") <img src="http://irtutor.com/media/SepFunnel_empty.jpg">(if:_x1 is 0)[<img src="http://irtutor.com/media/Flask1_empty.jpg">](else-if:_x1 is 10)[<img src="http://irtutor.com/media/Flask1_10ml.jpg">](else-if:_x1 is 20)[<img src="http://irtutor.com/media/Flask1_20ml.jpg">](else:)[<img src="http://irtutor.com/media/Flask1_30ml.jpg">](if:_x2 is 0)[<img src="http://irtutor.com/media/Flask2_empty.jpg">](else-if:_x2 is 10)[<img src="http://irtutor.com/media/Flask2_10ml.jpg">](else-if:_x2 is 20)[<img src="http://irtutor.com/media/Flask2_20ml.jpg">](else:)[<img src="http://irtutor.com/media/Flask2_30ml.jpg">] The upper layer was poured into flask 1 (if: $flask1Name is 0)[Label Flask 1 (optional):<input type="text" data-varname="flask1Name">\ <script>processInputElements();</script> ](else:)[ ($flask1Name)]. [[add drying agent to flask 1|dry E1]] [[add drying agent to flask 2|dry E2]] <!-- later, add back extraction of E1 or E2 with saturated NaCl--!> [[add acid dropwise to flask 1]] [[add acid dropwise to flask 2]] [[add base dropwise to flask 1]] [[add base dropwise to flask 2]] [[Extraction Start]]

(set: _drying to ($flask2's "phase" is "organic"), _x1 = $flask1's "volume", _x2 = $flask2's "volume")<img src="http://irtutor.com/media/SepFunnel_empty.jpg">(if: $flask1's "phase" is "solid")[<img src="http://irtutor.com/media/Flask1_evap.jpg">](else-if: $flask1's "phase" is "ppt")[<img src="http://irtutor.com/media/Flask1_filtered.jpg">](else:)[(if:_x1 is 0)[<img src="http://irtutor.com/media/Flask1_empty.jpg">](else-if:_x1 is 10)[<img src="http://irtutor.com/media/Flask1_10ml.jpg">](else-if:_x1 is 20)[<img src="http://irtutor.com/media/Flask1_20ml.jpg">](else:)[<img src="http://irtutor.com/media/Flask1_30ml.jpg">]](if:_drying)[<img src="http://irtutor.com/media/Flask2_dried.jpg">](else:)[<img src="http://irtutor.com/media/Flask2_10ml.jpg">] (if: _drying)[Adding sodium sulfate to flask 2 resulted in the white powder clumping and sinking to the bottom, but more added sodium sulfate remained free-flowing. The solution was transferred to a round bottom flask using a filter pipette, removing the drying agent. <iframe width="560" height="315" src="https://www.youtube.com/embed/uXA3My86P4k" frameborder="0" allow="accelerometer; autoplay; clipboard-write; encrypted-media; gyroscope; picture-in-picture" allowfullscreen></iframe> [[Evaporate flask 2 on rotavap]] ](else:)[Adding sodium sulfate to flask 2 resulted in the white powder clumping immediately and sinking to the bottom. Adding more sodium sulfate resulted in the same observation. Flask 2 contains an aqueous layer, and it is not possible to "dry" the aqueous layer. [[Extraction Start]] ]

(set: _drying to ($flask1's "phase" is "organic"), _x1 = $flask1's "volume", _x2 = $flask2's "volume")<img src="http://irtutor.com/media/SepFunnel_empty.jpg">(if:_drying)[<img src="http://irtutor.com/media/Flask1_dried.jpg">](else:)[<img src="http://irtutor.com/media/Flask1_10ml.jpg">](if: $flask2's "phase" is "solid")[<img src="http://irtutor.com/media/Flask2_evap.jpg">](else-if: $flask2's "phase" is "ppt")[<img src="http://irtutor.com/media/Flask2_filtered.jpg">](else:)[(if: _x2 is 0)[<img src="http://irtutor.com/media/Flask2_empty.jpg">](else-if:_x2 is 10)[<img src="http://irtutor.com/media/Flask2_10ml.jpg">](else-if:_x2 is 20)[<img src="http://irtutor.com/media/Flask2_20ml.jpg">](else:)[<img src="http://irtutor.com/media/Flask2_30ml.jpg">]] (if: _drying)[Adding sodium sulfate to flask 1 resulted in the white powder clumping and sinking to the bottom, but more added sodium sulfate remained free-flowing. This means there is no water remaining. The solution was transferred to a round bottom flask using a filter pipette, removing the drying agent. <iframe width="560" height="315" src="https://www.youtube.com/embed/uXA3My86P4k" frameborder="0" allow="accelerometer; autoplay; clipboard-write; encrypted-media; gyroscope; picture-in-picture" allowfullscreen></iframe> [[Evaporate flask 1 on rotavap]] ](else:)[Adding sodium sulfate to flask 1 resulted in the white powder clumping immediately and sinking to the bottom. Adding more sodium sulfate resulted in the same observation. Flask 2 contains an aqueous layer, and it is not possible to "dry" the aqueous layer. [[Extraction Start]] ]

(set:_x1 = $flask1's "volume", $flask2's "phase" to "solid") (display: "GraphicImages") <!--make sure there is something in the flask!--!> (if: ($flask2's "A" is not 0) or ($flask2's "N" is not 0))[The solid is now present in your flask 2. What would you like to do now?(set: $flask2's "done" to "yes") <iframe width="560" height="315" src="https://www.youtube.com/embed/113V95Hf8gw?start=134" frameborder="0" allow="accelerometer; autoplay; clipboard-write; encrypted-media; gyroscope; picture-in-picture" allowfullscreen></iframe> [[Weigh solid from flask 2 on the balance|Flask 2 solid mass]] [[Determine the melting point of the solid from flask 2|Flask 2 mp]]](else:)[Evaporation of the solvent in flask 2 results in no material present! [[Extraction Start]] ]

(set:_x1 = $flask1's "volume", _x2 = $flask2's "volume")<img src="http://irtutor.com/media/SepFunnel_empty.jpg">(if: $flask1's "phase" is "solid")[<img src="http://irtutor.com/media/Flask1_evap.jpg">](else-if: $flask1's "phase" is "NaOH")[(if:_x1 is 10)[<img src="http://irtutor.com/media/Flask1_10ml_ppt.jpg">](else-if:_x1 is 20)[<img src="http://irtutor.com/media/Flask1_20ml_ppt.jpg">](else:)[<img src="http://irtutor.com/media/Flask1_30ml_ppt.jpg">]](else:)[(if:_x1 is 0)[<img src="http://irtutor.com/media/Flask1_empty.jpg">](else-if:_x1 is 10)[<img src="http://irtutor.com/media/Flask1_10ml.jpg">](else-if:_x1 is 20)[<img src="http://irtutor.com/media/Flask1_20ml.jpg">](else:)[<img src="http://irtutor.com/media/Flask1_30ml.jpg">]](if: $flask2's "phase" is "solid")[<img src="http://irtutor.com/media/Flask2_evap.jpg">](else:)[(if:_x2 is 0)[<img src="http://irtutor.com/media/Flask2_empty.jpg">](else-if:_x2 is 10)[<img src="http://irtutor.com/media/Flask2_10ml.jpg">](else-if:_x2 is 20)[<img src="http://irtutor.com/media/Flask2_20ml.jpg">](else:)[<img src="http://irtutor.com/media/Flask2_30ml.jpg">]] (if:$flask1's "phase" is "NaOH")[ (set: $flask1's "phase" to "ppt") 3M HCl is added dropwise to flask 1. A precipitate forms and dissolves, until a drop of the solution turns blue litmus paper red, when the precipitate remains in the flask. <iframe width="560" height="315" src="https://www.youtube.com/embed/aKA-Fwz0Tqg" frameborder="0" allow="accelerometer; autoplay; clipboard-write; encrypted-media; gyroscope; picture-in-picture" allowfullscreen></iframe> [[filter solid in Buchner funnel]] ] (else:)[Sorry, this doesn't work. Later we'll see why, but for now all we can tell you is 'nope' [[Extraction Start]] ]

(set:_x1 = $flask1's "volume", _x2 = $flask2's "volume")<img src="http://irtutor.com/media/SepFunnel_empty.jpg">(if: $flask1's "phase" is "solid")[<img src="http://irtutor.com/media/Flask1_evap.jpg">](else:)[(if:_x1 is 0)[<img src="http://irtutor.com/media/Flask1_empty.jpg">](else-if:_x1 is 10)[<img src="http://irtutor.com/media/Flask1_10ml.jpg">](else-if:_x1 is 20)[<img src="http://irtutor.com/media/Flask1_20ml.jpg">](else:)[<img src="http://irtutor.com/media/Flask1_30ml.jpg">]](if: $flask2's "phase" is "solid")[<img src="http://irtutor.com/media/Flask2_evap.jpg">](else-if: $flask2's "phase" is "NaOH")[ (if:_x2 is 10)[<img src="http://irtutor.com/media/Flask2_10ml_ppt.jpg">](else-if:_x2 is 20)[<img src="http://irtutor.com/media/Flask2_20ml_ppt.jpg">](else:)[<img src="http://irtutor.com/media/Flask2_30ml_ppt.jpg">]](else:)[(if:_x2 is 0)[<img src="http://irtutor.com/media/Flask2_empty.jpg">](else-if:_x2 is 10)[<img src="http://irtutor.com/media/Flask2_10ml.jpg">](else-if:_x2 is 20)[<img src="http://irtutor.com/media/Flask2_20ml.jpg">](else:)[<img src="http://irtutor.com/media/Flask2_30ml.jpg">]] (if:$flask2's "phase" is "NaOH")[(set: $flask2's "phase" to "ppt") 3M HCl is added dropwise to flask 2. A precipitate forms and dissolves, until a drop of the solution turns blue litmus paper red, when the precipitate remains in the flask. <iframe width="560" height="315" src="https://www.youtube.com/embed/aKA-Fwz0Tqg" frameborder="0" allow="accelerometer; autoplay; clipboard-write; encrypted-media; gyroscope; picture-in-picture" allowfullscreen></iframe> [[filter solid in Buchner funnel]] ] (else:)[Sorry, this doesn't work. Later we'll see why, but for now all we can tell you is 'nope' [[Extraction Start]] ]

<!--we have to first confirm that E1 had the aqueous layer--!> <!-- the following is for extraction of a base with acid (if:$flask1's "phase" is "HCl")[ A precipitate forms when you add base to flask 1. We'll assume you keep adding acid until red litmus paper turns blue ](else:)[Sorry, this doesn't work. Later we'll see why, but for now all we can tell you is 'nope' [[Extraction Start]] ] --!> Sorry, this isn't going to work. [[Extraction Start]]

<!--we have to first confirm that E2 had the aqueous layer--!> <!-- the following is for extraction of a base with acid (if:$flask1's "phase" is "HCl")[ A precipitate forms when you add base to E1. We'll assume you keep adding acid until red litmus paper turns blue ](else:)[Sorry, this doesn't work. Later we'll see why, but for now all we can tell you is 'nope' [[Extraction Start]] ] --!> Sorry, this isn't going to work. [[Extraction Start]]

(display: "GraphicImages") (set: _result = $flask2's "N" + $flask2's "A") The mass of the solid in flask 2(if: $flask2Name is 0)[](else:)[ ($flask2Name)] is (print: _result.toFixed(4)) [[determine the melting point of the solid in flask 2|Flask 2 mp]] (if: $flask1's "done" is "no")[ [[add acid dropwise to flask 1]] [[add base dropwise to flask 1]] [[add drying agent to flask 1|dry E1]]](else:)[ [[Weigh solid from flask 1 on the balance|Flask 1 solid mass]] [[Determine the melting point of the solid from flask 1|Flask 1 mp]] [[Prepare final report]] ]

(display: "GraphicImages") (set: $moleFrac2 = $flask2's "A"/($flask2's "A" + $flask2's "N"))(if: $moleFrac2 > 0.5)[(set: $puremp = 122.3)](else:)[(set: $puremp = 80.26)](set: _eutectic = 66.85)(set: _mp=_eutectic+0.16*($puremp-_eutectic)*(5*$moleFrac2-2.5)*(5*$moleFrac2-2.5))(set: _mplow=_mp-(26-(10*$moleFrac2-5)*(10*$moleFrac2-5))) The melting point for the solid in flask 2(if: $flask2Name is 0)[](else:)[ ($flask2Name)] is observed to be (print: _mplow.toFixed(1)) to (print: _mp.toFixed(1)) degrees C. [[determine the mass of the solid|Flask 2 solid mass]] (if: $flask1's "done" is "no")[ [[add acid dropwise to flask 1]] [[add base dropwise to flask 1]] [[add drying agent to flask 1|dry E1]]](else:)[ [[Weigh solid from flask 1 on the balance|Flask 1 solid mass]] [[Determine the melting point of the solid from flask 1|Flask 1 mp]] [[Prepare final report]] ]

(display: "GraphicImages") Please enter the appropriate values: The solid isolated in Flask 1 is (dropdown: bind $Solid1, "unspecified", "benzoic acid", "naphthalene") and weighed <input type="text" data-varname="massSolid1">\ <script>processInputElements();</script> grams. This constitutes <input type="text" data-varname="pctSolid1">\ <script>processInputElements();</script> % of the starting mixture. The melting point data indicate this solid is (dropdown: bind $purity1, "unspecified", "pure", "impure") The solid isolated in Flask 2 is (dropdown: bind $Solid2, "unspecified", "benzoic acid", "naphthalene") and weighted <input type="text" data-varname="massSolid2">\ <script>processInputElements();</script> grams. This constitutes <input type="text" data-varname="pctSolid2">\ <script>processInputElements();</script> % of the starting mixture.The melting point data indicate this solid is (dropdown: bind $purity2, "unspecified", "pure", "impure") [[Grade Report]]

$studentName 's Report for Separation of a Mixture by Extraction (display: "GraphicImages") (set: _N1pct = 100*($flask1's "N")/$massN, _N2pct = 100*($flask2's "N")/$massN, _A1pct = 100*($flask1's "A")/$massA, _A2pct = 100*($flask2's "A")/$massA) (if: $flask1's "phase" is "solid" and $Solid1 is "naphthalene")[You identified solid in flask 1 correctly, and you isolated (print: _N1pct.toFixed(2)) percent of the substance.](else-if:$flask1's "phase" is "ppt" and $Solid1 is "benzoic acid")[You identified solid in flask 1 correctly, and you isolated (print: _A1pct.toFixed(2)) percent of the substance.](else:)[(colour: red)[Incorrect identification of solid in flask 1!]] (if: $flask2's "phase" is "solid" and $Solid2 is "naphthalene")[You identified solid in flask 2 correctly, and you isolated (print: _N2pct.toFixed(2)) percent of the substance.](else-if:$flask2's "phase" is "ppt" and $Solid2 is "benzoic acid")[You identified solid in flask 2 correctly, and you isolated (print: _A2pct.toFixed(2)) percent of the substance.](else:)[(colour: red)[Incorrect identification of solid in flask 2!]] (set: _mass1 to (num: $massSolid1), _mass2 to (num: $massSolid2))(set: _pctA = 100*$massA/($massA + $massN), _pctN =100*$massN/($massA+$massN))(if: $Solid1 is "naphthalene")[(set: $error1=_pctN-(num: $pctSolid1), $error2=_pctA-(num:$pctSolid2))Compare your calculated percent naphthalene in the mixture, $pctSolid1 % to the actual percentage (print: _pctN.toFixed(2)) %, and your calculated percent benzoic acid in the mixture $pctSolid2 % to the actual percentage (print: _pctA.toFixed(2)) %](else:)[(set: $error1=_pctN-(num: $pctSolid2), $error2=_pctA-(num:$pctSolid1))Compare your calculated percent benzoic acid in the mixture, $pctSolid1 %, to the actual percentage (print: _pctA.toFixed(2)) %, and your calculated percent naphthalene in the mixture, $pctSolid2 % to the actual percentage (print: _pctN.toFixed(2)) %](if: $error2 > .1 or $error1 > .1)[(colour: red)[Your percentages are incorrect. This could be a calculation error, or the result of isolating an impure solid.]] (if: $moleFrac1 < .99 and $moleFrac1 > 0.01)[(if: $purity1 is"impure")[You correctly recognized that the solid from flask 1 is impure. How could you have obtained purer material from the extraction?](else:)[(colour: red)[The solid from flask 1 is IMPURE!! How could you have obtained purer material from the extraction?]]](else:)[(if: $purity1 is "impure")[(colour: red)[The solid from flask 1 is PURE! Why did you think it was impure?]](else:)[You correctly recognized that the solid from flask 1 is pure.]] (if: $moleFrac2 < .99 and $moleFrac2 > 0.01)[(if: $purity2 is"impure")[You correctly recognized that the solid from flask 2 is impure. How could you have obtained purer material from the extraction?](else:)[(colour: red)[The solid from flask 2 is IMPURE!! How could you have obtained purer material from the extraction?]]](else:)[(if: $purity2 is "impure")[(colour: red)[The solid from flask 2 is PURE! Why did you think it was impure?]](else:)[You correctly recognized that the solid from flask 2 is pure.]] [[Try again|Extraction Start]]

(display: "GraphicImages") (set: _result = $flask1's "N" + $flask1's "A") The mass of the solid in flask 1(if: $flask1Name is 0)[](else:)[ ($flask1Name)] is (print: _result.toFixed(4)) [[determine the melting point of the solid in flask 1|Flask 1 mp]] (if: $flask2's "done" is "no")[ [[add acid dropwise to flask 2]] [[add base dropwise to flask 2]] [[add drying agent to flask 2|dry E2]]](else:)[ [[Weigh solid from flask 2 on the balance|Flask 2 solid mass]] [[Determine the melting point of the solid from flask 2|Flask 2 mp]] [[Prepare final report]] ]

(display: "GraphicImages") (set: $moleFrac1 = $flask1's "A"/($flask1's "A" + $flask1's "N"))(if: $moleFrac1 > 0.5)[(set: $puremp = 122.3)](else:)[(set: $puremp = 80.26)](set: _eutectic = 66.85)(set: _mp=_eutectic+0.16*($puremp-_eutectic)*(5*$moleFrac1-2.5)*(5*$moleFrac1-2.5))(set: _mplow=_mp-(26-(10*$moleFrac1-5)*(10*$moleFrac1-5))) The melting point for the solid in flask 1(if: $flask1Name is 0)[](else:)[ ($flask1Name)] is observed to be (print: _mplow.toFixed(1)) to (print: _mp.toFixed(1)) degrees C. [[determine the mass of the solid|Flask 1 solid mass]] (if: $flask2's "done" is "no")[ [[add acid dropwise to flask 2]] [[add base dropwise to flask 2]] [[add drying agent to flask 2|dry E2]]](else:)[ [[Weigh solid from flask 2 on the balance|Flask 2 solid mass]] [[Determine the melting point of the solid from flask 2|Flask 2 mp]] [[Prepare final report]] ]

(set:_x2 = $flask2's "volume", $flask1's "phase" to "solid") (display: "GraphicImages") <!--make sure there is something in the flask!--!> (if: ($flask1's "A" is not 0) or ($flask1's "N" is not 0))[ The solid is now present in your flask 1. What would you like to do now?(set: $flask1's "done" to "yes") <iframe width="560" height="315" src="https://www.youtube.com/embed/113V95Hf8gw?start=134" frameborder="0" allow="accelerometer; autoplay; clipboard-write; encrypted-media; gyroscope; picture-in-picture" allowfullscreen></iframe> [[Weigh solid from flask 1 on the balance|Flask 1 solid mass]] [[Determine the melting point of the solid from flask 1|Flask 1 mp]] ] (else:)[Evaporation of the solvent in flask 1 results in no material present! [[Extraction Start]] ]

(set:_x1 = $flask1's "volume", _x2 = $flask2's "volume")<img src="http://irtutor.com/media/SepFunnel_empty.jpg">(if: $flask1's "phase" is "solid")[<img src="http://irtutor.com/media/Flask1_evap.jpg">](else-if: $flask1's "phase" is "ppt")[<img src="http://irtutor.com/media/Flask1_filtered.jpg">](else:)[(if:_x1 is 0)[<img src="http://irtutor.com/media/Flask1_empty.jpg">](else-if:_x1 is 10)[<img src="http://irtutor.com/media/Flask1_10ml.jpg">](else-if:_x1 is 20)[<img src="http://irtutor.com/media/Flask1_20ml.jpg">](else:)[<img src="http://irtutor.com/media/Flask1_30ml.jpg">]](if: $flask2's "phase" is "solid")[<img src="http://irtutor.com/media/Flask2_evap.jpg">](else-if: $flask2's "phase" is "ppt")[<img src="http://irtutor.com/media/Flask2_filtered.jpg">](else:)[(if:_x2 is 0)[<img src="http://irtutor.com/media/Flask2_empty.jpg">](else-if:_x2 is 10)[<img src="http://irtutor.com/media/Flask2_10ml.jpg">](else-if:_x2 is 20)[<img src="http://irtutor.com/media/Flask2_20ml.jpg">](else:)[<img src="http://irtutor.com/media/Flask2_30ml.jpg">]] The precipitate is filtered through a Buchner funnel under reduced pressure. After rinsing with water, the solid is allowed to dry on the filter paper. (if: $flask1's "phase" is "organic")[ [[add drying agent to flask 1|dry E1]] ] (if: $flask2's "phase" is "organic")[ [[add drying agent to flask 2|dry E2]] ] (if: $flask1's "phase" is "ppt")[ (set: $flask1's "done" to "yes")[[Determine the mass of the precipitate from Flask 1|Flask 1 solid mass]] [[Determine the melting point of the solid in Flask 1|Flask 1 mp]] ](else:)[ (set: $flask2's "done" to "yes") [[Determine the mass of the precipitate from Flask 2|Flask 2 solid mass]] [[Determine the melting point of the solid in Flask 2|Flask 2 mp]] ] (if: $flask1's "done" is "yes" or $flask2's "done" is "yes")[ [[Prepare final report]] ]

The possible "phases" listed in $flask# are none - this means nothing is in the flask organic - the flask contains the organic (ether) layer NaOH - the flask contains the NaOH layer HCl NaCl solid - the flask contains the result of drying and evaporating the organic layer ppt - the flask contains the result of precipitating and filtering the aqueous layer The amounts present are under "A" and "N" in grams