42nd International Chemistry Olympiad Tokyo, July 19-28, 2010

Examination Procedures
• You have 5 hours to complete Tasks 1, 2, and 3. order you choose. • There will be an additional 15 minutes reading time before the start. • DO NOT begin working on the tasks until the START command is given. • When the STOP command is given at the end of the 5 hours, you must stop your work on the tasks immediately. A delay in doing so may lead to your disqualification from the examination. • After the STOP command has been given, wait in your lab space. will check your lab space. The problem booklet (this booklet) The answer booklet Your chosen TLC plates in zipper storage bags A and B with your student code (from Task 1) Your product and glass microfiber filter sheet in a crystallization dish with a lid in zipper storage bag C with your student code (from Task 1) • Do not leave the examination hall until you are instructed to do so by the supervisors. A supervisor The following items should be left behind: You may perform the tasks in any

• Safety is the most important issue in the laboratory. You are expected to follow the safety rules given in the IChO regulations. Safety glasses and lab coats must be worn at ALL TIMES. • If you behave in an unsafe manner, you will receive one warning before you are asked to leave the laboratory. If required to leave due to a second warning, you will receive a score of zero for the entire experimental examination. • NO eating or drinking is allowed in the laboratory. • In case of emergency, follow the instructions given by the supervisors.

Notes on the booklets and answer methods
Practical Problems 1 / 22

• You should take care to report answers to an appropriate number of significant figures. clean it carefully in the sink closest to you. Do not seal the envelope. Do not attempt to separate the sheets. • An official English version of this examination is available upon request if you require clarification. permitted with no loss of points. • Keep your answer booklet in the envelope provided. Discard used glass capillaries into a labeled plastic tube . A waste container (plastic beaker) is also available on each bench for aqueous waste.. • The answer booklet comprises 6 pages. Take out the booklet only when If you need to do rough calculations. for which you will be pardoned. 2010 • The problem booklet comprises 23 pages including cover page. Do not use the mechanical pencil for filling in the answer sheets. each such incident will result in the loss of 1 point from your 40 practical points. • Replacement of chemicals and laboratory ware will be provided if necessary. use the back of the sheets. Use the mechanical pencil provided only for experiments in Task 1. You may also use the calculator and the ruler provided. July 19-28. Other than the first.42nd International Chemistry Olympiad Tokyo. etc. • Use only the pen provided for filling in the answer sheets. Notes on the Examination • You may need to reuse some glassware during the examination.   Practical Problems 2 / 22 . Refilling of washbottle water is If this is the case. • You should confirm your student code inscribed on the booklets and write your name and student code on every answer sheet. • Contact a supervisor near you if you have any questions regarding the tasks or if you need a refreshment/toilet break. • All results must be written in the appropriate areas on the answer sheets. Results written elsewhere will not be graded. • Use the labeled waste containers under the hood or near the windows for disposal of liquids and solids. you write the answers.

95 183.91 140.91 101.01 6 N 14.06 K Ca 40.93 27 Ni 58.94 25 Fe 55.95 18 30.26 168.71 121.22 40 Nb Mo 92.24 150.96 Tc - 43 Ru Os Hs 108 76 44 Rh 77 45 Pd Pt Ds 110 78 46 Ag Au Rg 111 79 47 Cd Hg 80 48 In Tl 81 49 Sn Pb 82 50 Sb Bi 83 51 Te Po 84 52 I Xe Rn 86 54 88.00 2 Li 6.60 126.93 173.87 22 23 V Cr 52.76 127.04 238.42 107.42nd International Chemistry Olympiad Tokyo.22 195. 2010 Periodic table with relative atomic masses 1 2 3 4 5 6 7 8 9 10 11 12 13 14 15 16 17 18 H 1.41 114.03   Practical Problems 3 / 22 .36 151.94 11 3 Be 9. July 19-28.93 162.08 196.98 89-103 Rf - Mt - 109 La Ac 89 57 Ce Th 90 58 Pr Pa 91 59 Nd Pm Sm Eu - 60 61 62 63 Gd 96 - 64 Tb 97 - 65 Dy Cf 98 66 Ho 99 - 67 Er 100 - 68 Tm Yb 101 102 - 69 70 Lu 103 71 138.50 164.38 207.00 42 24 Mn 54.01 12 4 B 10.45 17 Ar 39.09 32 14 P S Cl 35.92 33 Se 78.18 10 Na Mg 22.00 16 8 F 19.08 20 Sc 44.81 5 C 12.72 72.47 37 Sr 87.69 28 Cu 63.23 192.25 158.59 204.00 9 Ne 20.33 178.04 231.12 140.21 190.91 144.30 Al 26.55 29 Zn 65.01 15 7 O 16.01 1 He 4.05 174.96 34 Br 79.91 137.96 157.98 13 Si 28.10 50.82 118.07 102.80 36 39.97 200.85 26 Co 58.91 106.38 30 Ga Ge 69.29 Cs Fr 87 55 Ba Ra 88 56 57-71 Hf 104 72 Ta Db 105 73 W Sg 106 74 Re Bh 107 75 Ir At - 85 132.99 19 24.90 53 35 Kr 83.93 167.97 32.87 112.94 41 Rb 85.64 31 As 74.84 186.97 U 92 Np - 93 Pu Am Cm Bk - 94 95 Es Fm Md No Lr - 232.90 131.96 39 21 Ti 47.2 208.62 38 Y Zr 91.91 95.49 180.

on the desk or on pipette rack): Büchner funnel with rubber adapter Clamp with muff (clamp holder) 200-mL conical beaker 300-mL conical beaker Diaphragm vacuum pump with tubing and connecter Glass capillary tube (in a plastic tube) Glass microfiber filter sheet in a crystallization dish with lid 2-mL graduated pipette 5-mL graduated pipette Magnetic stirrer 10-mm magnetic stirring bar 22-mm magnetic stirring bar 10-mL measuring glass pH test paper (in a zipper storage bag) 10-mL plastic graduated cylinder Plastic tube for used glass capillary 1 1 1 1 1 8 1 3 1 1 1 1 1 3 1 1 1 3 1 1 1 1 1 1 1 1 1 Number   Practical Problems 4 / 22 .42nd International Chemistry Olympiad Tokyo. 2010 Apparatuses Apparatuses For multiple tasks (on the desk or in Box 1): 20-mL beaker for taking a small portion of liquid to rinse inside of glassware Paper 2-mL pipette bulb 5-mL pipette bulb Pipette rack 200-mL plastic beaker for waste Safety bulb Spatula Stand 100-mL washbottle 500-mL washbottle For Task 1 (in Box 1. July 19-28.

on the desk or on pipette rack): 2-mL graduated pipette 5-mL graduated pipette Label (in a zipper storage bag) LED light box (in a zipper storage bag: do not remove from the bag at any time.) Nessler tube Nessler tube rack 50-mL volumetric flask 5-mL volumetric pipette 10-mL volumetric pipette For Task 3.1 (in Box 2 or on pipette rack): Burette Burette clamp 100-mL conical beaker Glass funnel (for transferring chemicals to a burette) 1-mL graduated pipette 5-mL volumetric pipette 20-mL volumetric pipette For Task 3. July 19-28.42nd International Chemistry Olympiad Tokyo.2 (in Box 2): 10-mL vial (in a zipper storage bag) Plastic Pasteur pipette Shared equipment: Gloves of various sizes 1 1 1 1 4 1 1 for each 1 1 1 4 1 5 1 2 1 1 1 1 6 1 2 1 1 10 1   Practical Problems 5 / 22 . 2010 Suction flask 10-mL test tube 100-mL test tube TLC developing chamber with lid TLC plate (in a zipper storage bag) Tweezers Zipper storage bags A and B for submission of TLC plates Zipper storage bag C for submission of glass microfiber filter sheet in a crystallization dish For Task 2 (in Box 2.

2010 UV lamp Cleaning tissue   Practical Problems 6 / 22 .42nd International Chemistry Olympiad Tokyo. July 19-28.

July 19-28.5 mol L-1 HCl) For Task 1 (in Box 1): 1.5 1g -dicarboxylic acid diethyl ester (C13H19NO4. NaHCO3 solution) Urea hydrogen peroxide (CH4N2O•H2O2.5 mol L-1 hydrochloric acid (0.42nd International Chemistry Olympiad Tokyo. 2010 Chemicals on Each Desk Chemical For multiple tasks (in Box 1): 0. CH3COOH-CH3COONa solution) Practical Problems Plastic bottle None listed None listed Plastic bottle None listed None listed Plastic bottle None listed None listed   7 / 22 .4-DHP_TLC) Ethanol (C2H5OH) Ethyl acetate (CH3COOC2H5) Heptane (C7H16) Potassium iodide (KI) Sodium metabisulfite (Na2S2O5) Saturated sodium hydrogencarbonate solution (Sat.4-dihydro-2. 1.0 mg of iron in 1 L 50 mL solution) (labeled as “Standard Fe(bpy)32+ solution 1”) Standard Fe(bpy)32+ solution 2 (containing 3.6-dimethylpyridine-3.6. UHP) For Task 2 (in Box 2): Sample solution (labeled as “Sample solution”) 30 mL Plastic bottle None listed None listed 10 mL 25 mL 20 mL 150 mg 1g 25 mL Vial Vial Glass bottle Glass bottle Glass bottle Glass bottle Glass bottle Glass bottle 36/37/38 36/37/38 11 11-36-66-67 11-38-50/53-6567 None listed 22-31-41 None listed 26 26 7-16 16-26-33 9-16-29-3360-61-62 None listed 26-39-46 None listed 17-2636/37/39-45 50 mL Plastic bottle None listed None listed Quantity Container R phrases S phrases 1g Vial 8-34 Standard Fe(bpy)32+ solution 1 (containing 2.4-DHP_powder) 1.4-DHP for TLC 3 mg (1. 1:1 mixture of acetic acid 50 mL and sodium acetate.0 mg of iron in 1 L 50 mL solution) (labeled as “Standard Fe(bpy)32+ solution 2”) Acetate buffer solution (pH 4.

2 %(w/v) 2.5 mol L-1 NaOH) 1 g L-1 toluidine blue (TB) aqueous solution (1 g L-1 C15H16N3SCl) 50 mL Plastic bottle 34 26-37/39-45 6 mL Dropper bottle None listed None listed   Practical Problems 8 / 22 .1 (in Box 2 or on the desk): Polysaccharide solution (labeled as 50 mL “Polysaccharide solution”) Poly(diallyldimethylammonium chloride) aqueous solution (PDAC) CH2 N+ ClCH2 Plastic bottle None listed None listed 240 mL Glass bottle None listed None listed H3C CH3 n Potassium poly(vinyl sulfate) aqueous solution (0.5 mol L-1 sodium hydroxide aqueous solution (0.2’-bipyridine aqueous 25 mL solution (0. monomer unit concentration) (0. 2010 0.1 mol L-1 disodium 25 mL hydrogenphosphate solution (0.0025 mol L-1 PVSK) CH2 CH O O S O O-K+ n 240 mL Glass bottle 36/37/38 26-36 0. July 19-28.2 %(w/v) C10N2H8) Sodium thioglycolate (C2H3NaO2S) 20 mg Plastic bottle None listed None listed Plastic bottle None listed None listed Vial 22-38 36 For Task 3.42nd International Chemistry Olympiad Tokyo.0025 mol L-1.1 mol L-1 Na2HPO4) 0.

42nd International Chemistry Olympiad Tokyo. 2010 For Task 3. July 19-28.2 (in Box 2): Solution X-1 (X: A-H) Solution X-2 (X: A-H) Solution X-3 (X: A-H) Solution X-4 (X: A-H) Solution X-5 (X: A-H) 10 mL 10 mL 10 mL 10 mL 10 mL Dropper bottle Dropper bottle Dropper bottle Dropper bottle Dropper bottle 36/37/38 26-36   Practical Problems 9 / 22 .

2010 Risk Phrases Number 8 11 22 31 34 36 38 41 65 66 67 Special Risks Contact with combustible material may cause fire. July 19-28. Causes burns Irritating to eyes Irritating to skin Risk of serious damage to eyes Harmful: may cause lung damage if swallowed. 36/37/38 50/53 Irritating to eyes.   Practical Problems 10 / 22 . Repeated exposure may cause skin dryness or cracking. respiratory system and skin Very toxic to aquatic organisms. Vapors may cause drowsiness and dizziness. may cause long term adverse effects in the aquatic environment. Highly flammable Harmful if swallowed Contact with acids liberates toxic gas.42nd International Chemistry Olympiad Tokyo.

Wear suitable gloves and eye/face protection 24/25 36/37/39 37/39   Practical Problems 11 / 22 . Keep away from sources of ignition . gloves and eye/face protection. do not induce vomiting: seek medical advice immediately and show the container or label Avoid contact with skin and eyes. July 19-28. Keep container in a well ventilated place. 2010 Safety Phrases Number 7 9 16 17 26 29 33 36 37 39 45 46 60 61 62 Safety Recommendations Keep container tightly closed. Keep away from combustible material. If swallowed. In case of contact with eyes. seek medical advice immediately.42nd International Chemistry Olympiad Tokyo. Refer to special instructions/ material safety data sheet. Wear suitable gloves. Wear suitable protective clothing. Do not empty into drains. This material and its container must be disposed of as hazardous waste. Avoid release to the environment.No Smoking. (Show the label where possible. rinse immediately with plenty of water and seek medical advice. Wear eye/face protection. Take precautionary measures against static discharges.) If swallowed. seek medical advice immediately and show the container or label. Wear suitable protective clothing. In case of accident or if you feel unwell.

(4) Check your TLC plates before using. O H CH3CH2 O O H3C N H O O CH3 CH2CH3 N H N H H O H CH3CH2 O H3C N O O CH3 CH2CH3 UHP O O H KI 1.5-dicarboxylic acid diethyl ester (1.) (3) For thin layer chromatography (TLC) analysis. Add 1 mL of ethyl acetate to the vial (labeled as 1. take a small portion of the mixture using a If they are damaged. graduated pipette.4-DHP (1 g) (labeled as 1. 1.4-DHP_TLC) to dissolve 1. they can be replaced without penalty. When the reaction mixture becomes clear (the precipitates may form when it cools.4-dihydro-2. (2) Add 1 g UHP (wear gloves) and stir the mixture. Fig. (5) During the reaction. exothermic. 2010 Task 1 Reaction of Hantzsch Ester with Urea Hydrogen Peroxide In this experiment.4-DHP_powder). prepare a mixture of ethyl acetate:heptane (1:2 in volume) with a measuring glass and place an appropriate amount of the mixture in a TLC developing chamber.4-DHP or Hantzsch ester) by oxidation with urea hydrogen peroxide (UHP).4-DHP Procedures (1) Place a 22-mm magnetic stirring bar in a 100-mL test tube. Draw a start line on the lower portion of a TLC plate with a pencil (see (Caution: this reaction is Add 1. with a 5-mL   Practical Problems 12 / 22 . and potassium iodide (150 mg) to the test tube. Fix the test tube on a magnetic stirrer using a clamp.42nd International Chemistry Olympiad Tokyo. an environmentally-friendly oxidant.6-dimethylpyridine-3. but precipitates will not affect the TLC analysis). followed by ethanol (5 mL).4-DHP (3 mg). you are required to synthesize a pyridinedicarboxylate derivative from 1. the reaction mixture becomes clear (usually within 20 min).1). July 19-28.

Visualize the spots using a UV lamp (254 nm) and draw a line around the UV-active spots on the TLC clearly with the pencil.1 Spots on the TLC plate before development. iv. 1. Büchner funnel. 1.4-DHP solution prepared in procedure (3) in the center and left positions. so that there are three spots on the plate. 1.4-DHP. (6) Set up the suction filtration equipment (see Fig. (7) Add water (5 mL) to the reaction mixture using a 10-mL plastic graduated cylinder.42nd International Chemistry Olympiad Tokyo. iii. 1.2).2 TLC plate placed in the TLC developing chamber. 1.3). Load an appropriate amount of the 1. Fig. Add sodium metabisulfite (1 g). Place a glass microfiber filter sheet on the funnel.1). ii. transfer the contents of the tube (including the stirring bar) into a 200-mL conical beaker and wash the Practical Problems Fig. X: 1. Y: Reaction mixture. Develop the TLC plate in the TLC chamber (see Figs.   13 / 22 . July 19-28. Mark the solvent front with the pencil. rubber adopter. 1. with the center spot containing both the reaction mixture and 1.] marked “A.” Place the last TLC plate in a zipper storage bag X X+Y Y Fig. Repeat the TLC analysis after ten minutes. Assess the completion of the reaction based on the TLC results.3 Suction filtration equipment: i. diaphragm vacuum pump.4-DHP in the reaction mixture. if you find significant amounts of 1. Place a Büchner funnel fitted with a rubber adapter onto the suction flask. Connect the suction flask to the diaphragm vacuum pump. [Note that you will perform TLC analysis again in procedure (8).1 and 1. suction flask. 2010 glass capillary and load it to make two spots in the center and right positions on the TLC plate.4-DHP (see Fig.

Mark the solvent front and the spot(s).” c) Draw the structural formula of the organic cation before adding sodium hydrogencarbonate. if any. skip this filtration process. Add saturated sodium hydrogencarbonate solution in small Filter the precipitate formed through the portions using a 2-mL graduated pipette until the pH of the aqueous phase becomes just over 7 (check the pH with pH test paper). Place the 200-mL conical beaker on the magnetic stirrer and stir the solution. Avoid placing the stirring bar in the dish. Cover the dish with the lid marked with your code. July 19-28. precipitate with a small portion of water. Place a 10-mm magnetic stirring bar in the test tube and fix it securely with the clamp.” If you detect the product on the TLC plate. product remaining in the filtrates. add more (9) At this stage. precipitate. vigorously for 30 seconds on the magnetic stirrer. 2010 test tube with water (30 mL). Transfer the filtrate (2 mL) to a 10-mL test tube using a 2-mL graduated pipette. zipper storage bag marked “B. Place the crystallization dish with the lid in a zipper storage bag marked “C. filter and wash it. e) Submit the following: i) TLC plate in bag “A” Give the chemical formula(e) of If you find no   Practical Problems 14 / 22 . and wash the Suck air through the precipitates for a minute procedure (5). if you find a precipitate formed. Place your product and the glass microfiber filter sheet in the crystallization dish. d) What is (are) the final product(s) derived from UHP? the product(s).42nd International Chemistry Olympiad Tokyo. (8) Transfer the filtrate from the suction flask to a 300-mL conical beaker.” a) Copy (sketch) the TLC plate in bag “A” on your answer sheet. (10) Suck air through the precipitate for 10 minutes to dry the product. saturated sodium hydrogencarbonate solution. Add 1 mL of ethyl acetate to the test tube using a 2-mL graduated pipette and stir the solution Stop stirring and wait for the solution Analyze the upper layer by TLC to see if there is any Spot the filtrates on the plate in the same way as Place the TLC plate in a Büchner funnel with suction using the diaphragm vacuum pump. to dry the product. to separate into two layers. b) Determine and record the Rf values (to the 2nd decimal place) of the spots on the TLC plate in bag “A.

42nd International Chemistry Olympiad Tokyo. 2010 ii) TLC plate in bag “B” iii) Your product and filter paper in the crystallization dish placed in bag “C”   Practical Problems 15 / 22 . July 19-28.

In this technique. you will learn to employ this technique by conducting measurements A and B. “sample 1. July 19-28. l is the pass length and ε is the molar absorption coefficient. The amount of Fe(bpy)32+ complex can be quantified by visual colorimetric measurement using Nessler tubes. the concentration can be calculated from that of the reference solution with a known concentration and the height of the column of each solution based on the Lambert-Beer law: A = εcl where A is the absorbance. 5 mL of 2.   Practical Problems 16 / 22 . 5 mL of disodium hydrogenphosphate solution (to mask Fe(III)).42nd International Chemistry Olympiad Tokyo.00 mL of sample solution into a 50-mL volumetric flask.00 mL of sample solution into a 50-mL volumetric flask using appropriate pipettes for each and dilute the resulting solution with water to the 50-mL mark. This solution is named Allow it to stand for at least 20 min to fully develop color. 5 mL of 2. and then you will determine the concentrations of Fe(II) and Fe(III) with measurements C and D. Procedures (1) Add 5 mL of acetate buffer solution. The depths of colors of the two solutions are balanced by adjusting the heights of liquid columns of the solutions. a pair of Nessler tubes is used. one is filled with a reference solution. but an accuracy of less than ±5% can be achieved. When the colors look the same.” (2) Add 5 mL of acetate buffer solution. Fe(bpy)32+.2’-bipyridine (bpy) to form an intensely red complex.2’-bipyridine solution and 5. First. This is a quite simple technique that was employed before photoelectric instruments were generally available. c is the concentration. 2010 Task 2 Determination of Fe(II) and Fe(III) by visual colorimetry In this experiment. you are required to determine Fe(II) and Fe(III) in a given sample solution which simulates a dissolved magnetite ore by visual colorimetric analysis involving a color reaction between Fe(II) and 2. Then add 20 mg of sodium thioglycolate powder (in excess) to reduce Fe(III) to Fe(II).2’-bipyridine solution and 10. Dilute the solution with water to the Then stopper the flask and mix the solution well. and the other is filled with a solution to be tested.

Nessler tube rack.D. LED light box in a zipper storage bag. A possible way to estimate the true value is to take an average between the values of lower and higher limits. Pour the solution to be measured into the other tube. Estimate your   Practical Problems 17 / 22 . if you adjust the height of the liquid column of the test solution only by increasing (or decreasing) the volume. The appropriate value for the height of For the test solution.1 Visual colorimetric measurement: i. and then compare its depth of color with that of the reference solution by looking downward through the solutions toward the LED light box.1). This solution is named “sample 2. ii. 2. Pour the provided “standard Fe(bpy)32+ solution 1” into one tube to an appropriate height (70 – 90 mm is recommended) from the bottom (etched marks on the tube indicate fixed heights from the bottom in mm) and use this as a reference for measurements A . stopper the flask and mix the solution well. Instructions for visual colorimetric measurement Set a pair of Nessler tubes on a Nessler tube rack placed on an LED light box (do not remove it from the bag at any time) and turn on the light (see Fig. you could reach a lower (or higher) value than the true one. July 19-28. h. 2. iii. 2010 50-mL mark. Fig. reading to at least 1 mm. Nessler tube.42nd International Chemistry Olympiad Tokyo. Allow it to stand for at least 20 min. Adjust the height of the liquid column of the test solution by adding or removing the solution with a graduated pipette until the depth of color in the two tubes is identical.” (3) Perform visual colorimetric measurements A – D based on the “Instructions for visual colorimetric measurement” shown below. should be determined by taking the range into the consideration. example. power switch. Note that the depths of color in a certain range may be recognized as identical to human eyes. iv.

) Then add more test solution until you recognize that the colors have become different from each other. Measurement C: Perform measurement of sample 1. and then pour the test solution into the other Nessler tube until the colors of the two solutions match each other.   Practical Problems 18 / 22 . the heights should IDEALLY be the same. a) Report your results for measurement A using the table provided on the answer sheet. c) Report your results for measurement C using the table provided on the answer sheet. b) Report your results for measurement B using the table provided on the answer sheet. h and h’. July 19-28. e) Express the concentration of the test solution. d) Report your results for measurement D using the table provided on the answer sheet. f) Calculate the concentrations of Fe(II) and Fe(III) in the original sample solution in mg L-1. Measurement D: Perform measurement of sample 2. Measurement B: Perform a measurement of “standard Fe(bpy)32+ solution 2” as a test solution using “standard Fe(bpy)32+ solution 1” as a reference. (When the colors match. pour the reference both the reference and the test solutions. solution into a Nessler tube to achieve an appropriate height. c. c’. 2010 Measurement A: Perform a measurement using “standard Fe(bpy)32+ solution 1” as In this measurement. and the height of each liquid column.42nd International Chemistry Olympiad Tokyo. Report both the lower and higher limits of the height of the liquid column of test solution with the same depth of color as the reference solution. using the concentration of the reference solution.

A back-titration technique is utilized.4 mL of 0. July 19-28. (2) Take precisely 5 mL of the polysaccharide solution and 20 mL of the PDAC solution using volumetric pipettes into another conical beaker.   Practical Problems 19 / 22 . poly(diallyldimethylammonium) (provided as its chloride salt. PDAC). the polysaccharide becomes a polyanion. which will then be utilized to Repeat if necessary.0025 mol L-1 PVSK (monomer unit concentration) standard solution. Report the PVSK solution volume (in mL) consumed in the standardization of PDAC. and 2 drops of TB to the solution. Add 0. 3.5 mol L-1 NaOH (The appearance of Titrate the resulting blue solution with the PVSK Repeat if necessary. 1a) The endpoint is determined In this task. when the color remains purple for 15-20 seconds.05 mL. Upon addition of polycation. identify polymers in the second part. standard solution in a similar manner. PDAC solution is standardized using the standard solution of potassium poly(vinyl sulfate) (PVSK). 2010 Task 3 Polymers in Analysis Polymers can be used in various analyses. the color turns purple. You are asked to determine the concentrations of these two groups by colloid titration under the basic and acidic conditions based on the differences in the protonation behavior of these acid groups.1 Analysis of Polysaccharide by Colloid Titration You are provided with a solution of a polysaccharide containing sulfonate (-SO3-) and carboxylate (-COO-) groups. becomes gradually turbid as the endpoint approaches. Procedures (1) Take precisely 20 mL of the PDAC solution using a volumetric pipette into a 100-mL conical beaker. At the endpoint of colloid titration. When these acid groups are ionized. you are first required to analyze a polysaccharide using a polymer-polymer interaction.42nd International Chemistry Olympiad Tokyo. Record your reading to 0. the number of anionic groups becomes equal to that of cationic groups. Add 2 drops of toluidine blue (TB) into the conical beaker. Note that the solution resulting blue solution with the 0. Titrate the At the endpoint. it forms a polyion complex.

(or -COOH) groups (in mol L-1) in the given polysaccharide solution. July 19-28.(or -SO3H) groups and the -COO. 1c) Record your reading to 0.5 mol L-1 NaOH.5 mL of 0. Mark the acid group(s) ionized under the basic conditions on the answer sheet. 2010 coagulation may be different. Mark the acid group(s) fully ionized under acidic conditions on the answer sheet.05 mL. 1d) Report the PVSK solution volume (in mL) consumed in the titration under acidic conditions.05 mL. (3) Repeat procedure 2 above with the addition of 0.5 mol L-1 HCl instead of 0.42nd International Chemistry Olympiad Tokyo. depending on the pH of the solution. Calculate the concentrations of the -SO3. 1e) 1f) Record your reading to 0.   Practical Problems 20 / 22 .) 1b) Report the PVSK solution volume (in mL) consumed in the titration under basic conditions.

monomer unit concentration). and each solution contains one of the compounds below (all of which are used). triethylene glycol. PEO. carrying out the following procedures.]   Practical Problems 21 / 22 . 2010 3. poly(sodium 4-styrenesulfonate). Remind that you have only 10 mL of each solution. MW.05 mol L-1 (for polymers. in which an interaction takes place between the two polymers. 2) The volume of a solution measuring 5 mm in height from the bottom of the vial is approximately 1 mL. poly(diallyldimethylammonium chloride) Helpful comments 1) Aggregates observed in Task 3. PMANa. They can be utilized to identify polymer samples.2 Identification of compounds You are provided with five solutions (X-1~5. July 19-28. Your task is to identify all the compounds by HOCH2CH2OCH2CH2OCH2CH2OH (TEG) CH3 CH2CH2O (PEO) n CH2 C COONa n (PMANa) CH2 CH CH2 N+ Cl- CH2 SO3Na n (PSSNa) H3C CH3 n (PDAC) [Abbreviations: TEG. poly(ethylene oxide). “X” designates your sample code. PDAC. stands for molecular weight. The concentration is 0.1 could be observed when mixing two polymer solutions in an appropriate combination. PSSNa. which is a letter in the Roman alphabet from A to H).42nd International Chemistry Olympiad Tokyo. poly(sodium methacrylate).

July 19-28. you can acidify the resulting mixture. For each solution. Identify the compound in each solution based on the experimental results. to indicate your =========================== (22. (2) If necessary. mark one of the five boxes to indicate your identification. You are also asked to fill in the blanks with one of the letters in the Roman alphabet.5 mol L-1 HCl) from a plastic Pasteur pipette are sufficient for this purpose. 2010 Procedures (1) Mix similar volumes of two solutions together in a vial. from A to H.575 characters without spaces)   Practical Problems 22 / 22 . Ten drops of hydrochloric acid (0. sample code.42nd International Chemistry Olympiad Tokyo.

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