Investigating Organic Functional Groups. Chromium, permanganate, and methylene chloride are toxic and should be used with caution
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- Edward Morgan
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From this document you will learn the answers to the following questions:
What is done to give a carbonyl and green chromium compound?
What should you use hromium , permanganate , and methylene chloride?
What university is responsible for the lab where you can find toxic chemicals?
Transcription
1 Austin Peay State University Department of hemistry hem 1021 autions hromium, permanganate, and methylene chloride are toxic and should be used with caution Purpose In this lab you will use traditional chemical tests to identify a variety of functional groups in known chemicals. You will use those positive results to identify the functional groups present in an unknown compound. Introduction hemists today are trained to use elaborate technologies and instrumentation to determine chemical structure and makeup. owever, many years ago, these technologies were not yet available, and there were very few ways for chemists to determine the composition of any chemical. hemists would use a series of tests to characterize the structure and makeup of a chemical. You will be doing some of these tests in this lab, in particular, ones that indicate functional groups present on a molecule. Functional groups can be defined as the parts of organic molecules that are prone to chemical reactions. Saturated hydrocarbons (carbon chain molecules with all single bonds and the maximum number of hydrogen atoms) are not especially susceptible to reactions, but chemicals that contain oxygen, nitrogen, halogens (Br, l, F, and I) and double or triple bonds between carbon atoms can readily react in specific conditions. Alkenes, alcohols, aldehyde, ketone, and alkyl halide compounds will be studied. Alkenes Alkenes are chemicals that contain a carbon-carbon double bond as the functional group. They react with the magenta-colored chemical potassium permanganate (KMnO 4 ) to product manganese dioxide (MnO 2 ), which is a brown solid. In other words, you can determine if a chemical has a double bond by adding KMnO 4 and looking for the development of the brown solid MnO 2. Example 1: Oxidation of 1-butene by KMnO 4 O O 2 KMnO MnO 2 2KO O Alcohols An alcohol is any organic compound that has a hydroxyl functional group (-O) bonded to a carbon atom, which is usually connected to other carbon or hydrogen atoms. Alcohols are oxidized with Jones reagent (chromic acid, 2 ro 4 ) and sulfuric acid ( 2 SO 4 )) to give a carbonyl (=O) and a green chromium compound. Positive identification of an alcohol will be evident when the addition of chromic acid results in a green solution. This reaction is quick, working on the order of 2-3 seconds. Aldehydes also react with chromic acid to produce the green chromium compound, but the reaction takes a bit longer, seconds or so. Revision SP11 IB Page 1 of 9
2 Austin Peay State University Department of hemistry hem 1021 Example 2: Reduction of 2-propanol (iso-propanol) ro ro 3 2 O O O Ketones and Aldehydes Ketones and aldehydes both contain the same functional group, a carbon-oxygen double bond. In a ketone, the carbon atom is also attached to two other carbons. In an aldehyde, the carbon is bonded to another carbon and a hydrogen. Both ketones and aldehydes react with a chemical called 2,4-dinitrophenylhydrazine (2,4-DP) to form a yellow or orange solid within a few minutes. Example 3: Reaction of propanone (a ketone) with 2,4-DP O O O O O 2 O 2 2,4-DP Example 4: Reaction of ethanal (an aldehyde) with 2,4-DP O O O O O 2 O 2 2,4-DP Alkyl alides Alkyl halides are alkanes that have a halide ion (such as chloride or bromide) bonded to carbon in the usual place of a hydrogen atom. alides in organic compounds can be identified by way of a Beilstein test. A copper wire is heated under a flame to from a layer of copper(ii) oxide (uo) on the wire. Dip the coated wire in your compound and then place under the flame. If a halide is present in the organic compound, it reacts with copper(ii) to form a copper halide, which burns green in the flame. Example 5: Identification of methyl bromide by Beilstein test u(s) flame 3 Br uo(s) ubr 2 Revision SP11 IB Page 2 of 9
3 Austin Peay State University Department of hemistry hem 1021 Investigating an unknown The different tests described above can be combined and used in a systematic way to identify the functional groups present in an unknown compound. In industry, the steps required to test an unknown can be assembled into a standard operating procedure or SOP. Sometimes the steps are outlined in a flowchart; please note, it is important to perform the tests in order. Some tests, such as the test for alkenes with permanganate, give positive results for more than one functional group, so following the outlined procedure is particularly important to obtain clear results. Procedure Keep the resulting test tubes from your standard tests until the end of the experiment for comparison to your unknown compound. Use hexanes as your control. 1. Testing for alkenes: Set up two small disposable test tubes in the test tube rack. In tube one, put in 4 drops of the control. In tube two, put in 4 drops of the alkene. Add 2 ml of ethanol to each tube. Add two drops of the permanganate solution, stopper, and shake (be careful you know which tube is which!) Record the results on the data sheet. 2. Testing for alcohols: Set up two new small disposable test tubes in the test tube rack. In tube one, put in 1 drop of the control, and in tube two put in one drop of the alcohol. Add 1 ml of acetone to each tube followed by 1 drop of the Jones reagent. Gently swirl the tubes. Record the results on the data sheet. 3. Testing for ketones: Set up two small disposable test tubes in the test tube rack. In tube one, put in 2 drops of the control, and in tube two, put in 2 drops of the ketone. Add 2 ml of ethanol to each tube followed by 3 ml of the 2,4-DP reagent. Stopper and shake well. Let the solution stand for up to 15 minutes. You can go onto the next test while waiting. After 15 minutes, record the results on the data sheet. 4. Testing for aldehydes: You will be using two tests for aldehydes, the chromic acid test as well as the 2,4- DP test. Because you already know what the negative tests for these look like (tube 1 from step 1), you will only be doing the positive tests. Set up two small disposable test tubes in the test tube rack. In tube 1, put in 1 drop of aldehyde, 1 ml of acetone, and 1 drop of chromic acid (Jone s reagent). Swirl the tube. In tube 2, put in 2 drops of aldehyde, 2 ml of ethanol, and 3 ml of the 2,4-DP reagent. Stopper and shake the tube. Wait up to 15 minutes for a reaction in tube 2. ompare the tests to the positive and negative tests in 2 and 3 above. Record the results on the data sheet. 5. Testing for alkyl halides: Take a small length of copper wire and brush it clean using the sand paper. old it over a flame for about 30 seconds. Take it out of the fire and let it cool down. Dip the wire in control and hold over the flame. Repeat the procedure using the alkyl halide. It may be necessary to repeat the dip/burn cycle a few times to see the desired change. Record the results on the data sheet. Revision SP11 IB Page 3 of 9
4 Austin Peay State University Department of hemistry hem Testing your unknown: Obtain your unknown and perform the tests described in steps 1-5. For example, substitute unknown for alkene in step 1. Make careful observations and record your results on the data sheet. ompare to the results to those for the known chemicals to determine the functional groups present in your compound. Flowchart for Identifying Unknown ere are the tests you should perform on your unknown. TEST 1: Treat unknown with potassium permanganate reagent. unknown = alkene, alcohol, or aldehyde. TEST 2: Treat unknown with Jones reagent. - unknown = ketone or alkyl halide. TEST 3: Treat unknown with 2,4- dinitrophenylhydrazine (2,4-DP) reagent. unknown = alcohol or aldehyde. TEST 4: Treat unknown with 2,4- DP reagent. unknown = ALDEYDE. - unknown = ALOOL. - unknown = ALKEE. unknown = KETOE. - unknown = ALKYL ALIDE. TEST 5: Treat with copper wire over flame (Beilstein test) to confirm an alkyl halide. unknown = ALKYL ALIDE. Waste Disposal ollect all chemicals in the appropriate waste container. lean-up Wash all glassware with soap then rinse 3 times with tap water, and once with deionized water. Revision SP11 IB Page 4 of 9
5 Austin Peay State University Department of hemistry hem 1021 Data Sheet 1 ame: Lab Partner: Test Sample (expected result) Observations Alkene Test exanes (-) ame: () Alcohol Test exanes (-) ame: () Ketone Test Aldehyde Tests exanes (-) ame: () Reaction with hromic acid () Reaction with 2,4-DP () Alkyl alide Test exanes (-) ame: () Revision SP11 IB Page 5 of 9
6 Austin Peay State University Department of hemistry hem 1021 Data Sheet 2 Unknown umber: ame of Test Observations Positive () or egative (-)? Revision SP11 IB Page 6 of 9
7 Austin Peay State University Department of hemistry hem 1021 Post-lab Assignment ame: 1. Which functional group is present in your unknown chemical? Explain your reasoning using the results of the tests performed on your unknown. 2. Using what you have learned in this lab, is there a way to identify an alkene which also has an alcohol group? If yes, which tests would you use and why? 3. What complications may arise from one test giving a positive result for two different functional groups? Revision SP11 IB Page 7 of 9
8 Austin Peay State University Department of hemistry hem 1021 This page left blank for double-sided printing. Revision SP11 IB Page 8 of 9
9 Austin Peay State University Department of hemistry hem 1021 Pre-lab Assignment ame: 1. Draw the Lewis-dot structures of the compounds listed below that you will be using in this lab. ircle and name the functional group. a) exane d) Ethanol b) Acetone e) exanal c) Propene f) Methylene chloride 2. ame and circle the functional groups shown in the compounds below. Which test would you use for the following chemicals? 3 a) b) 3 O Revision SP11 IB Page 9 of 9
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