CH110 (F2023) Experiment 1 - Vitamin C in Supplements

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CH110 – Experiment #1 – Fall 2023 1 EXPERIMENT 1. Determination of Vitamin C in Vitamin Supplements How to prepare for the first CH110 Lab: 1. On MyLS, go to CH-110-1A or CH-110-1C à Content à Experiment 1. Download, print and read the Experiment 1 handout. 2. Complete WHMIS and send the completed certificate to Dr. AB ( ubistrivoda@wlu.ca ). (WHMIS is available from the “Self-Registration” tab on the MyLS home page, see Lab Syllabus for more information). 3. Bring the Experiment 1 handout to the first lab. 4. Purchase and bring your lab coat and safety glasses to the first lab. 5. (Optional ) Bring a lock to store your belongings safely in the free lockers outside of the lab during lab time. Jackets, backpacks, cellphones and laptops are not allowed in the lab. 6. Wear appropriate lab attire (covered legs and feet, no sandals allowed). 7. Bring a calculator and pen. 8. Review textbook sections 4.5 to 4.9. OBJECTIVE: The objective of today’s experiment is to use volumetric analysis to determine the amount of Vitamin C (ascorbic acid) in two types of individual supplement brands – Jamieson ® and Equate ® . Then, by compiling data from your experiment (qualitative, quantitative and class data), determine if the two supplement brands contain the accurate amount of Vitamin C as advertised on the bottle (500mg). LEARNING OUTCOMES Analyze and solve problems in a consistent and organized manner Solve mass number – molar mass type problems Perform common unit conversions Balance chemical reactions Calculate the amount of product from the amounts of the reactants and a balanced chemical reaction Draw hydrocarbons using the IUPAC system THEORY Vitamins are organic constituents of food that are essential for life. Not only do they prevent what is known as 'vitamin deficiency diseases' (scurvy, pellagra, and beriberi), they perform specific tasks in metabolic processes that are vital to growth regulation, tissue replacement, and general cellular activity. There are two categories of vitamins: fat-soluble and water-soluble. The fat-soluble vitamins (A, D, E, and K) are stored in the body and are not readily lost in cooking water or destroyed at cooking temperatures. Since these vitamins are stored in the body, they can be taken in one large dose to be used over an extended period. However, avoid overdosing on fat-soluble vitamins because the accumulation of large quantities of these vitamins can cause harm.
CH110 – Experiment #1 – Fall 2023 2 Water-soluble vitamins (C and B complex) are not stored in the body, are easily leached into the cooking water, and are destroyed by light and heat. Since they are not stored in the body, these vitamins must be ingested in small quantities at frequent intervals. For example, the Reference Daily Intake (RDI) of vitamin C (ascorbic acid) for adults and children over the age of 4 is 60 mg/day. This value, however, is only enough to reduce the risk of scurvy. Much higher doses are required for optimum health. Taking large doses quickly, say greater than 500 mg, increases urinary excretion since vitamin C is water-soluble, so the doses should be taken in small amounts throughout the day. The side effects of vitamin C overdosing can include diarrhea and increased flatulence. One way to obtain the RDI of vitamins is through supplements . Supplements can either be extracted from natural sources (such as citrus fruits) or chemically synthesized. It is very cost-efficient to chemically synthesize Vitamin C. In addition, it contains remarkably high potency that works effectively and can be produced in a small tablet making it more user-friendly. In the case of this experiment, the chemically synthesized supplements from Jamieson ® and Equate ® each claim to contain 500mg of vitamin C per tablet. One method of synthesizing ascorbic acid that is most used involves the fermentation of corn sugar to eventually form a ketoacid, which can then be converted into L-Ascorbic acid. Various additives are included in the manufacturing of these supplements to enable the human body to properly process the supplement. For tasting purposes, artificial flavours and aromas are normally added as well. In this experiment, the vitamin C is quantified by titration of the pure ascorbic acid (an analyte) with iodine, I 2(aq) solution (a titrant, usually delivered from a burette). The titrant, the iodine solution of known concentration, is reduced by vitamin C while vitamin C is oxidized. The indicator used in this experiment is a 1% starch solution. When the ascorbic acid (vitamin C), C 6 H 8 O 6 in the supplements is oxidized by the iodine three colourless products are formed: dehydroascorbic acid (C 6 H 6 O 6 ), hydrogen ions, and iodide ions (reaction 1). (1) The equivalence point occurs when the quantity of titrant equals the amount of analyte. This is an ideal, theoretical result however, what we measure in this experiment is an endpoint of the titration, marked by an indicator colour change. An indicator is a substance that will change colour once all analyte is consumed, and excess titrant is detected. Therefore, when all the ascorbic acid in the sample has been oxidized, the next drop of iodine is free to react with the starch (indicator) and a blue-black starch-I 2 complex is formed. This signals the endpoint of the titration . When ascorbic acid reacts with iodine, is known as a reduction-oxidation or redox reaction . Electrons are transferred in this reaction. If an element or compound loses electrons, the reaction is
CH110 – Experiment #1 – Fall 2023 3 referred to as the oxidation reaction . If an element or compound gains electrons is called a reduction reaction . An easy mnemonic tool to remember this is “LEO the lion says GER”. LEO stands for “Losing Electrons – Oxidation” and GER represents “Gaining Electrons – Reduction”. The loss and gain of electrons can be shown easily by breaking up the overall reaction into two half- reactions. For example, zinc metal displaces hydrogen ions from aqueous solutions of acids according to equation 2: Zn (s) + 2H + (aq) Zn 2+ (aq) + H 2 (g) (2) In this case, zinc loses electrons in the oxidation half-reaction 3: Zn (s) Zn 2+ (aq) + 2e - (3) while hydrogen gains electrons in the reduction half-reaction 4. 2H + (aq) + 2e - H 2 (g) (4) The symbol e - represents a single electron with one negative charge. In any redox reaction, the number of electrons transferred must be the same between each half-reaction and each half-reaction must be balanced both with several atoms and total charge. An oxidizing agent is a substance that takes electrons from another substance. A reducing agent is a substance that gives electrons to another substance, helping the reduction take place. In the example above, zinc is the reducing agent, and hydrogen ions are the oxidizing agent. One of the ways to identify if a redox reaction is occurring is to determine the oxidation number or state of the substances involved. There are several rules to follow when determining the oxidation number that can be found in your textbook . Read the rules first to help in the determination of oxidation numbers in organic compounds. For the reaction example listed below, the oxygen and hydrogen are labelled -2 and +1 respectively. Example – Consider the following reaction used in the Breathalyzer test to determine the amount of ethanol on the breath of people who are suspected of driving while under the influence of alcohol. 3CH 3 CH 2 OH ( g ) + 2Cr 2 O 7 2- ( aq ) + 16 H + ( aq ) 3CH 3 CO 2 H ( aq ) + 4Cr 3+ ( aq ) + 11H 2 O ( l ) (5) The unbalanced oxidation half-reaction is CH 3 CH 2 OH ( g ) CH 3 CO 2 H ( aq ) . Since each carbon is not identical, the oxidation numbers must be determined separately as follows: (6)
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CH110 – Experiment #1 – Fall 2023 4 The carbon atom in the -CH 3 group in ethanol is assigned an oxidation state of -3 so that it can balance the oxidation states of the three H atoms it is bonded to. In the -CH 2 OH group, the oxygen, and three hydrogens are labelled first giving a total of (-2) +3(+1) = +1. To balance this part of the molecule, the carbon must have an oxidation state of -1. The carbon in the -CH 3 group in the acetic acid formed in this reaction has the same oxidation state as it did in the starting material: -3. There is a change in the oxidation number of the other carbon atom, however, from -1 to +3. The carbon must have an oxidation number of +3 to balance the 2(-2) x 1(+1) = -3 total provided by the two oxygens and the hydrogen. Therefore, the oxidation half-reaction must have a loss of four electrons by one of the carbon atoms. The chromate ion (Cr 2 O 7 2- ) is involved in the reduction half-reaction. In this experiment, titration is performed using a burette , a glass tube that allows you to measure the volume of liquid delivered through the valve (stopcock) at the bottom. The amount of iodine dispensed can be measured by reading the liquid level before and after titration and subtracting the first reading from the final reading. When reading the amount of iodine in the burette, your eye should be at the same height as the top of the liquid. Since the liquid surface forms a concave meniscus , a precise reading should be obtained at the bottom of the meniscus. For better accuracy, try to deliver one drop at a time near the endpoint of the titration. Ensure to swirl the flask to mix all the contents and to ensure that the droplets that may be on the walls of the flask are in the final solution. CLASS DATA: For this experiment, you will have to calculate the mean and standard deviation of the data collected by the whole class (data will be available on MyLS after all the lab sections have completed the lab). As with most measurements, there will be some variability between each group’s reported Vitamin C amount (mg). Statistical analysis will be performed on these samples, which allows us to calculate the mean (the average) and standard deviation (variability between samples) to determine whether and how much the set of data is closely related. Mean or average is the sum of measured values divided by the number of measurements. mean = !"# %& #’(!")’* +(,"’! (&%) .()/01",() /2.’ %& %)(34’ 5"01’ !"..,’#’3/) 3"#7’) %& #’(!")’#’3/! Standard deviation is a measure of how close the data is to the mean. The smaller the standard deviation, the more closely data is clustered around the mean. Both the mean and the standard deviation, although can be calculated using mathematical formulas, for this experiment will be calculated using the Microsoft Excel program. In this program, you will have to use the formula in the worksheet to direct the program to calculate your values. Please see your “To Excel in Chemistry” Assignment for more guidance on how to perform these calculations. Figure 1 : The bottom of the concave meniscus must be read precisely. The correct volume reading for the burette is 20.70 mL.
CH110 – Experiment #1 – Fall 2023 5 PROCEDURE Note: Each lab bench will be assigned only one kind of vitamin C supplement – either 500mg Jamieson ® tablet or 500mg Equate ® tablet. Record on your data sheet which supplement you have been given. Amounts of Vitamin C obtained by your classmates (Class data) for both supplement brands will be shared for comparison purposes on MyLearningSpace (MyLS). A. Preparing Vitamin C Stock Samples Steps #1-3 below will be completed for you by the Lab Instructor. You must complete steps 4-6. 1. Place the entire 500 mg tablet to be used in a clean 250 mL Volumetric flask (See Figure 2 on the next page). 2. Add deionized water to roughly half full in the volumetric flask. 3. Cover the flask and swirl until the sample is completely dissolved. ---------------------------------------- 4. Remove the cap and then fill the flask with deionized water such that the bottom of the meniscus is exactly at the etched line. DO NOT go past the etched line. It will be helpful to use a disposable pipette looking at eye level to fill to the line. 5. Cap the top tightly and mix by inverting 10-15 times. This will be your Vitamin C stock solution. 6. Record qualitative observations for both types of supplements (Jamieson & Equate). Figure 2 : Proper procedure to prepare a solution in a Volumetric flask from a solid sample. B. Titration of Vitamin C Sample 1. The burette will be set up at your lab bench using a burette clamp and retort stand. Obtain approximately 15 mL of the 0.0037M iodine solution and run it through the burette to clean it.
CH110 – Experiment #1 – Fall 2023 6 Collect the 15 mL rinse from the burette in a 150 mL beaker and dispose of it in the hazardous waste fume hood at the end of the lab. 2. Carefully fill the burette with the 0.0037M iodine solution to approximately the 0.00 mL mark (or slightly above, then release iodine slowly down to the 0.00 mL mark). Remove all bubbles/air pockets from the tip of the burette (right under the stopcock). Ensure the funnel is out of the burette. 3. Record the actual initial volume in the burette to two decimal places on your data sheet. 4. Transfer 10.0 mL of the stock solution into a clean 250 mL Erlenmeyer flask. 5. Fill the flask to approximately the 100 mL mark with deionized water. 6. Add 10 drops of starch indicator and swirl the flask. 7. Place the Erlenmeyer flask under the burette and on a white piece of paper to better detect the endpoint. 8. Titrate by slowly adding the iodine solution from the burette as you gently swirl the flask. Flashes of blue/purple color will begin to appear in the flask. Continue until the endpoint is reached, as indicated by the persisting blueish color . Record the endpoint burette volume to two decimal places on your data sheet. (See Figure 1). 9. Repeat steps 4-8 two more times for a total of three titrations . You may need to refill the burette before beginning the second and/or third titration. 10. Once you are done with all 3 titrations, dispose of the rest of the solutions in a hazardous waste container in the fume hood. 11. Wash all your dishes (glassware) except for the burette. 12. Complete Table 3 on your Data Sheet and calculate milligrams of vitamin C for each of the three trials (before you leave the lab) . Remember to account for the preparation of the stock solution. 13. Record the average value of vitamin C (in mg) on the whiteboard before you leave. 14. Obtain the Lab Coordinator’s signature on your Datasheet. 15. LATER THIS WEEK: Check MyLS later this week to download the Vitamin C results from your classmates (Class data). You will need it to complete Question 4 of your Lab Report.
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CH110 – Experiment #1 – Fall 2023 7 LAB REPORT (Full Lab Report) More information on how to write a Lab Report & what should be included in your lab report is provided in your Lab syllabus (pg. 9-12). Please note that you must write a Full Lab Report for this lab (you must write an Abstract, Procedure Reference, Results, Lab Question Answers, Discussion and Conclusion sections). A few important notes: - Results section (retype ALL your qualitative and quantitative data, present in Tables with descriptive titles) - Answer questions 1-6 below - Lab Report must be typed up. - Scan or take an image of your data sheet (must be submitted with the lab report) QUESTIONS 1. Calculate the amount of Vitamin C (in mg) present in your supplement AND the stock solution (Data Sheet, Table 3). Show the complete calculations (for all the values in Table 3) including ALL units for one trial only. Ensure you have the correct number of significant figures in the final answer. (3.5 marks) 2. Calculate the percentage error between your sample (use average) (experimental value) and the reported value (500 mg) (accepted value). Use the formula given below (Accepted value is also called “true” value or “theoretical” value) (1 mark): Percentage error = |Accepted value − Experimental value| Accepted value x 100% 3a). Using Excel, calculate the mean class value and standard deviation for the amount of ascorbic acid found in each of the two supplements. (Refer to Excel Assignment 1 for help with calculations!) (1 mark) 3b). Calculate the percentage error between mean class data and each supplement's reported mg of Vitamin C (500 mg). One sample calculation is required. (1 mark) 3c). Create a labelled table to summarize your data. You must include a descriptive title. (1 mark) 4. Identify the reducing agent in the experimental redox reaction. Explain how you determined this using a chemical reaction (1 mark). Insert your academic integrity statement here.
CH110 – Experiment #1 – Fall 2023 8 5. The polymer starch used as an indicator in our reaction can be oxidized by NaOCl, according to the reaction below. Draw (only one repeating unit required) and identify (by circling) exactly the carbon atom(s) on starch that are being oxidized. State the oxidation number of the carbon atom(s) before and after the reaction. (2 marks) 6. Write balanced, labelled oxidation and reduction half-reactions for the overall redox reaction (the titration of ascorbic acid with iodine) in this experiment. Refer to Section 4.6 in your text (Tro, Cdn Ed.) for additional assistance. (2 marks)
CH110 – Experiment #1 – Fall 2023 9 Experiment 1. Vitamin C Data Sheet Name: _________________________________________________________________ Table 1 . Qualitative Observations (description of each supplement, observations before, during and after titration). Jamieson Supplement Equate Supplement Iodine Starch indicator Before titration During titration After titration Table 2 . Burette readings for your titration of vitamin C with iodine (read to 2 decimal places): Trial 1 Trial 2 Trial 3 The volume of Vitamin C Stock Solution used (mL) *should be 10 mL of close to 10mL The volume of iodine used (mL) *Final burette reading (mL)
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CH110 – Experiment #1 – Fall 2023 10 Table 3. Experimental data and calculated results to determine the mass of ascorbic acid in the 10.0mL titration of a supplement with iodine. Type of Vitamin C Supplement (circle one) Jamieson Equate The concentration of iodine solution used (M) 0.0037M Trial 1 2 3 The volume of iodine used (from Data Sheet Table 2) (L) *convert to L Moles of iodine (mol) (calculate) Moles of ascorbic acid (mol) * remember ratio 1:1 at endpoint Mass of ascorbic acid (g) (calculate) Mass of ascorbic acid in the 10 mL sample (mg) (calculate) Mass of ascorbic acid in 250 mL stock solution (mg) (calculate) The average mass of ascorbic acid (mg (calculate) *hint: it should be close to 500mg, if not, check your calculations Note: Datasheets must be written in pen and submitted with your lab report. Lab Instructor’s Initials: ______________
CH110 – Experiment #1 – Fall 2023 11 Marking Scheme (Experiment 1) Abstract 3.0 Procedure reference – see Lab Syllabus (pg.9-12) on how to reference the procedure section 0.5 Results retype ALL your Data sheet. Every table must have an appropriate, descriptive title 3.0 Lab Report Questions 12.5 Discussion 3.0 Conclusion 1.0 Datasheet Must be written in pen Submit a scan/photo 0.25 Academic Integrity Statement (AIS) 0.25 SPT Mark Please see syllabus for more information. 2.0 Total marks 25.5 Remember: Handing in a partial lab report, even late, is better than handing in nothing. I am here to help! Please don’t hesitate to ask questions!! References: Adapted from: Wilfrid Laurier University Chemistry Department. Fall 2022. Chemistry CH110 Laboratory Manual Fall 2022. Pages 1-135 Wilfrid Laurier University, ON, Canada