A student separated a 2-g mixture of fluorene, 2-naphthoic acid, and diphenylamine (shown below) dissolved in 25 mL of the organic solvent diethyl ether.The separation experiment was performed according to the following steps:Step 1The mixture solution was partitioned by pouring it into a separatory funnel containing 10 mL water, and the organic layer was extracted with 10 mL 1 M NaOH(aq).Step 2The aqueous layer was transferred to Flask A, and concentrated HCl(aq) was added dropwise to the flask until pH paper indicated that the solution was acidic. Flask A was then placed in ice water to induce precipitate formation.Step 3The organic layer was extracted with 10 mL 3 M HCl(aq). The resulting aqueous layer was then transferred to Flask B and 8 M NaOH was added dropwise to Flask B until pH paper indicated that the solution was basic. Flask B was then placed in ice water, to maximize precipitate formation.Step 4The precipitates in flasks A and B were collected separately by vacuum filtration, rinsed with distilled water, and dried in an oven.Step 5The organic layer was transferred into Flask C and dried by adding anhydrous MgSO4 to remove any residual water present. The organic solvent was separated from the MgSO4 in Flask C by gravity filtration, and the solvent was evaporated, yielding white crystals.Step 6The purity of the three isolated compounds was analyzed by thin-layer chromatography (TLC) on silica plates. A sample of the mixture was spotted on the TLC plate as a reference in addition to the isolated compound. Question 41In which of the following steps is 2-naphthoic acid separated from the mixture?A.Step 1B.Step 3C.Step 4D.Step 5
Question
A student separated a 2-g mixture of fluorene, 2-naphthoic acid, and diphenylamine (shown below) dissolved in 25 mL of the organic solvent diethyl ether.The separation experiment was performed according to the following steps:Step 1The mixture solution was partitioned by pouring it into a separatory funnel containing 10 mL water, and the organic layer was extracted with 10 mL 1 M NaOH(aq).Step 2The aqueous layer was transferred to Flask A, and concentrated HCl(aq) was added dropwise to the flask until pH paper indicated that the solution was acidic. Flask A was then placed in ice water to induce precipitate formation.Step 3The organic layer was extracted with 10 mL 3 M HCl(aq). The resulting aqueous layer was then transferred to Flask B and 8 M NaOH was added dropwise to Flask B until pH paper indicated that the solution was basic. Flask B was then placed in ice water, to maximize precipitate formation.Step 4The precipitates in flasks A and B were collected separately by vacuum filtration, rinsed with distilled water, and dried in an oven.Step 5The organic layer was transferred into Flask C and dried by adding anhydrous MgSO4 to remove any residual water present. The organic solvent was separated from the MgSO4 in Flask C by gravity filtration, and the solvent was evaporated, yielding white crystals.Step 6The purity of the three isolated compounds was analyzed by thin-layer chromatography (TLC) on silica plates. A sample of the mixture was spotted on the TLC plate as a reference in addition to the isolated compound. Question 41In which of the following steps is 2-naphthoic acid separated from the mixture?A.Step 1B.Step 3C.Step 4D.Step 5
Solution
2-naphthoic acid is separated from the mixture in Step 2. This is because 2-naphthoic acid is an acid and will react with the base (NaOH) in Step 1 to form a salt, which is soluble in the aqueous layer. This aqueous layer is then transferred to Flask A. When concentrated HCl is added in Step 2, the salt is converted back to 2-naphthoic acid, which is not soluble in water and precipitates out. Therefore, the correct answer is not listed among the options A, B, C, or D. The separation of 2-naphthoic acid actually occurs in Step 2.
Similar Questions
Step 1The mixture solution was partitioned by pouring it into a separatory funnel containing 10 mL water, and the organic layer was extracted with 10 mL 1 M NaOH(aq).Step 2The aqueous layer was transferred to Flask A, and concentrated HCl(aq) was added dropwise to the flask until pH paper indicated that the solution was acidic. Flask A was then placed in ice water to induce precipitate formation.Step 3The organic layer was extracted with 10 mL 3 M HCl(aq). The resulting aqueous layer was then transferred to Flask B and 8 M NaOH was added dropwise to Flask B until pH paper indicated that the solution was basic. Flask B was then placed in ice water, to maximize precipitate formation.Step 4The precipitates in flasks A and B were collected separately by vacuum filtration, rinsed with distilled water, and dried in an oven.Step 5The organic layer was transferred into Flask C and dried by adding anhydrous MgSO4 to remove any residual water present. The organic solvent was separated from the MgSO4 in Flask C by gravity filtration, and the solvent was evaporated, yielding white crystals.Step 6The purity of the three isolated compounds was analyzed by thin-layer chromatography (TLC) on silica plates. A sample of the mixture was spotted on the TLC plate as a reference in addition to the isolated compound. Question 41In which of the following steps is 2-naphthoic acid separated from the mixture?A.Step 1B.Step 3C.Step 4D.Step 5
Which of the following separation techniques could be used to separate a mixture of two substances based on their solubility?FlotationEvaporationFiltrationDistillation
A student wants to separate substances by filtration. They write a method for the experiment but not in the correct order as shown. 1. Pour the mixture through the funnel into the conical flask. 2. Fold the filter paper. 3. Collect the filtrate in the conical flask. 4. Put the filter paper into the funnel. 5. Collect any insoluble substances on the filter paper.
Organise these steps on performing liquid-liquid extraction between water and diethyl ether in the correct sequence. Use the simulation and video below to help you if you need it.Using a separating funnel simulationUsing a separating funnel video Group of answer choicesStep 1Step 2Step 3Step 4Step 5Step 6Step 7Step 8Step 9Step 10Step 11Step 12
a method of separating and analyzing mixtures of chemicals according to solubility
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