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    EPSON039

    Hochgeladen von

    Jihee Yoon
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    © All Rights Reserved
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    Preparation of |-Bromobutane Lab Report/Page | of 5 NAME Locker No. Dare PREPARATION OF 1-BROMOBUTANE LAB REPORT PRE-LAB: ‘SHOW (1) THE REACTION AND (2) THE MECHANISM (WITH ARROWS): TABLE OF REACTANTS AND PRODUCTS (YOU DO NOT NEED TO FiLL IN THE SHADED AREAS): — re Mew cad TIGUROUOT as var SGC TTT az = nd TaaT me Bees ‘mass (G) psa : eer 7 Banal Tom : ‘OBid Sa eee : a7 coal TF 1. One of the reagents s H2S04. Why do you need to add this reagent slowly and carefully (there are two reasons)? 2. Once your reaction is completed, you will be transferting your mixture to @ separatory funnel. Why is ft necessary to dain the lower layer quickly and IMMEDIATELY? Instructor's Initials Preparation of 1-Bromobutane Lab Report/Page 2 of 3 RESULTS What was the actual yleld of your final product? UTANE EXERCISES 1. Determine the percent yleld of your product. (Show ll of your calculations) 2. What was the limiting reagent? b. Whet was the theoretical yield? Wet was your percent yield? 4. IF your yield was low (less thon 60%), explain why you think this happened. Preparation of !-Bromobutane Lab Report/Page 3 of 5 2. This Is a $N2 reaction. Why does the preparation of 1-bromobutane follow this mechanism rather than an SN mechanism? 3. Inthe procedure, you were told whether the aqueous layer was the top layer or bottom layer. If you hod net been told this, and did not have access to information about the densities of your reactants and products, and did not have ‘access fo any other chemicals, how could you have quickly determined which layer was the organic layer? 4. Why did you need to vent the separatory funnel after you had added the sodium bicarbonate (be specific? ‘What was the purpose of using the following techniques inthis synthesis? + Heating ot refx + Washing the product with water + Weshing the product with NoHCO3 + Adding enhydrous ealclum chloride Prep of 1-Bromobutane Procedure/Page | of 5 Chem 501 Summer 2016 PREPARATION OF 1-BROMOBUTANE CALICO + \,50, + her — cipicelker + tho + felSo,- In this procedure, you will prepare 1-bromobutane from 1-butanol using a substitution reaction under ‘acidic conditions. This is on Sx2 reaction. The mechanism is shown below. The purpose of the sulfuric acid is to first protonate the weakly bosic hydroxyl group and thereby convert itto a good leaving group. It ‘can then leave as neutral water. The mechanism is S¥2. Br : — sonore” CHyCH_CH:CH,Br + HO PROCEDURE CAUTION: WEAR GLOVES DURING THE ENTIRE EXPERIMENT 1. Set up your equipment in your hood, as shown in the pre-lab demo. 2. Take your 100 ml round-bottom flask, wide stem funnel, and cork ring to one of the balances, and measure out 17 g of NaBr into the flask. Return flask to your hood and clamp to the ring stand. Add 15 mL of distiled H2O and 10 mL of 1-butanol to the flask. 4. Add your magnetic stirring bar, ond begin stirring the contents of the flask. The flask should be in contact with the hotplate. 5. Bring @ 50 oF 100 mL beaker to the front of the lab ond dispense 15 ml cone. H2SO4. This is concentrated acid, so make sure to cover the beaker with a watch glass or another beaker, and walk back to your station carefully. SLOWLY AND CAREFULLY add the conc. H25Ox to the flask. 7. Equip the flask with a reflux condenser and begin circulating water through it~ water going in at the bottom and out of the top of the condenser. 8. Heat the flask gently (using the hotplate at setting of about “4"). Continue gentle heating until the mixture begins to reflux (liquid is seen dripping from the condenser). 9. Once this is observed, continue refluxing the mixture for 60 minutes, controlling the heat so that the level of the vapor in the condenser reaches no more than half-way up the condenser. 10. During the reflux period, complete the previous lab by determining the melting point of your recrystallized unknown, and doing the mixed melting point determination, which will allow you to Identify your unknown compound. 12. 13. 15, 16. 17. 18, 19. 20. 21 Prep of 1-Bromobutane Procedure/Page 2 of Chem 301 Summer 2016 Prepare a waste beaker by adding 700 ml of water to your 1 L beaker. You ond your hood partner can share one beaker. (During the washings, you will be pouring your aqueous layers into this beaker, as the aqueous layer will contain unreacted concentrated acid, and this will allow the acid to be diluted before being poured down the drain.) At the end of the 60-minute reflux period, discontinue heating. At this point, you will have two separate layers. The top layer is the organic layer and contains the 1-brombutane; the bottom layer is the aqueous layer. Once the contents of the flask ceases to bubble, remove the reflux condenser, unclamp the flask from the ringstand, and pour the contents of the flask into your 250 ml separatory funnel. Do not allow your magnetic stirrer to fall into the funnell IMMEDIATELY drain the LOWER aqueous layer into @ beaker and then add it to the contents of your TL beaker, WITH STIRRING. Wash the organic layer using 15 ml of H2O. (In other words, add 15 ml of H20 to the organic layer that remains in your separatory funnel. Stopper the sep funnel, invert and vent to release any ‘gases, then gently shake, and retum the funnel fo the ringstand and allow the two layers to separate.) Separate the UPPER aqueous layer from the organic layer and add it tothe contents of your 1L waste beaker, WITH STIRRING. (In other words, drain the lower organic layer into your Erhlenmeyer flask, ond pour the upper aqueous layer into your waste becker.) ‘Wash the organic layer with 15 mL saturated sodium bicarbonate. Make sure that once you have ‘added the sodium bicarbonate, you gently invert and then vent the separatory funnel several times until you no longer hear the sound of gas escaping from the vented funnel. This gas is CO2, which is. produced when the sulfuric acid droplets that remain are neutralized by the sodium bicarbonate. Drain the lower ORGANIC layer into @ DRY 50 ml Erlenmeyer flask, and add CaCl. ‘Swirl the flask occasionally for a period of two minutes. Allow the drying agent to settie and DECANT the liquid into previously-weighed product bottle, appropriately labeled, and weigh again so that you can determine the weight of your final product. Store your product in your locker for use in the olky! halide tests. ‘The waste beaker containing your aqueous layers can be poured down the sink, while flushing with water. The drying agent that is remaining after decanting your product can be diluted with water and flushed down the sink. Save your product for the alkyl halide tests, to be performed next lab period. Prep of l-Bromobutane Procedure/Page 3 of Chem 301 Summer 2016 NOTES Steps 1-9 HBr is not available commercially, so itis prepared “in situ", meaning “in solution: NaBr + H2SO1 —» HBr + NaHSO« ‘You must add the H2SOx slowly and carefully for two reasons. If itis added too quickly, the HBr which forms can oxidize to form bromine molecules. Also, this reaction is exothermic, so you must add the sulfuric ‘cid slowly and carefully to avoid a run-away reaction. (However, the reaction loses energy quickly, so then energy must be supplied by heating in order to push the reaction towards completion.) Steps 8-9 Refiuxing is a means of trapping the vapors of the reactants and cooling them enough to return to the reaction flask, where they can continue to react. Step 14 | cannot emphasize enough to drain the lower, aqueous layer IMMEDIATELYIII The aqueous layer contains NalSOs, and if you do not drain this layer quickly and immediately, crystals will form that will clog the drain in the separatory funnel. ‘Steps 18-17 To purify the 1-bromobutane, a series of washings is performed. If you get confused about which layer is ‘organic or aqueous, remember what you learned during the Extraction procedure we did earlier. To determine which layer is which, you can drain a small amount of the lower layer into a test tube and then ‘add an equal amount of water. If two separate layers are observed, then the lower layer is the organi layer. If not, itis the aqueous layer. Step 15, ‘Woshing with water removes any unreacted H2SO« molecules, as well as any unreacted 1-butanol. Remember the Extraction procedure you practiced previously! This means to add the solvent, stopper the funnel, invert the separatory funnel and vent to release any built-up gases; repeat until there is no sound ‘of gas venting, then gently shake and replace the funnel back in the ringstand, and separate the two layers. Step 1Z ‘Washing with saturated NaHCO3 removes any remaining H2SO4 molecul Steps 18-19. ‘Any residual water is removed by adding CaCl2. Remember to add the drying agent in small amounts, ‘and add just enough so that when the flask is swirled, the drying agent floats freely in the flask ond ‘quickly setties to the bottom. Make sure to swirl for a full two minutes, so that the drying agent has enough time to come into full contact with any residual water molecules. Your solution should be clear; if itis cloudy, there is stil residual water. CHOCHZCHICH2OH + H2S04 + NaB 17 9 NoBr 15 mL H20 10 ml 1-betanol Initial reaction it exothermic, but Quidkly loses energy, so ada! heat is needed. organic layer cequecus layer v¥ Drain lower aqueous layer. Leave organic layer in funnel. ‘equecus layer ‘organic layer Drala lower organic layer i Enrlenmeyer flask. Pour out aqueous layer into waste beaker, to 15 ml H2S04 dd slowly Transfer 40 separatory funnel and drain the lower aqueous layer. —_— Retlux for 60 min Trops the vapors of reactants ond cools them so they return to the flask end have ‘onother opportunity to react. IMMEDIATELY Step 15 Extract organic loyer with H20 (add 15 mL H20 to organic ae —— ony unreacted H2S04 Step.1Z Retum organic layer to funnel ‘and add 15 ml NaHCO2, Dry orgonic layer over CaClz Removes sesidual water. —> Prep of 1-Bromobutane Flow Chart CHacHacHaCHaBr + H20 + NaHSO« upper organic layer contains 1-bromobutane lower aqueous layer ‘contains unreacted H2S04, unreacted NoBr. “a wae organi layer. Pour out aqueous layer into ‘waste beaker Decant into product bottle. Weigh and label. (Don't forget to first ‘weigh the botie when empty.) Save for alky| halide tests prep of alky} halides lecture notes/page | of + PREPARATION OF ALKYL HALIDES LECTURE NOTES (PREP OF 1-BROMOBUTANE AND 2-CHLORO-2-METHYLBUTANE) Hove students begin the experiment. Demonstrate the use of the condenser in refluxing. Lecture during the 60-minute reflux period. They will also need to complete the Recrystallization procedure (melting point and mixed melting point). Cover the prep of 1-bromobutone, the prep of 2- chloro-2-methylbutane and the olky/ halide fess. You will prepare two alkyl halides from their corresponding alcohols, which will then be used to perform two alkyl halide classification tests. Three-part experiment run over two weeks: * Preparation of 1-bromobutane from 1-butanel (primary alcohol) * Preporation of 2-chloro-2-methylbutane from 2-methyl-2-butanol (tertiary alcohol) * Run classification tests of both products Alcohols do net undergo nucleophilic substitution reactions because hydroxide ion is strongly basic and a poor leaving group. Thus, alkyl bromides cannot be prepared by either an Sx2 or an Sn! reaction upon heating alcohols with bromide salts. However, alcohols readily undergo nucleophilic substitutions if the hydroxyl group is first activated to produce a better leaving group. This is the basis for nearly all of the reactions of alcohols. (On of the easiest methods for activating on alcohol for a nucleophilic substitution reaction is to protonote the hydroxyl oxygen with a strong acid in the presence of a nucleophile. The protonated hydroxyl group can now leave as «weakly basic water molecule instead of as a strongly basic hydroxide ion. If the alcohol is primary, the protonated hydroxy! is readily displaced by a nucleophile in an x2 reaction, whereas, if the alcohol is tertiary, the protonated hydroxyl-carbon bond fragments to form a carbocation bby an SN1 process, which then reacts with a nucleophile to form a substitution product. Alcohols are easily converted into the corresponding alkyl halides by reacting them with concentrated ‘aqueous hydrogen halides. Tertiary alcohols react almost instantly at cool temperatures via an Sx ‘mechanism, since tertiary carbocations are relatively easy to form. Primary alcohols, on the other hand, react via the Sx2 mechanism, becouse primary cations are difficult to form. Addition of a strong acid forms an oxonium ion from the primary OH group, changing a poor leaving group into a good one. In spite or this, Because a primary cation is too hard to form, water does not actually leave until itis pushed ‘out by an incoming nucleophile (the bromide ion, in this case). Note that this is an equilibrium process, so the reaction cannot be expected to go 100% to completion. Prep of 1-Bromobutane from 1-Butanol w/e CHCH,CH.CH;OH +H® ChyCHg CHC H CHCHZCH,CHRBE + H,0 The Sx2 reaction (also known as bimolecular nucleophilic substitution) is a type of nucleophilic substitution, where a lone pair from a nucleophile attacks an electron deficient electrophilic center and bonds to it, expelling another group called a leaving group. Thus the incoming group replaces the leaving group fone step. Since two reacting species ore involved in the slow, rate-determining step of the reaction, this leads to the name bimolecular nucleophilic substitution, or Sx2. prep of alky} halides lecture notes/page 2 of + Alcohols do not undergo nucleophilic substivtion reactions because the hydroxide ion is strongly basic and 's © poor leaving group. However, alcohols readily undergo nucleophilic substitutions ifthe hydroxyl group is first activated to produce a better leaving group. This is the basis for nearly all of the reactions of alcohols. (One of the eosiest methods for activating an olahol for a nucleophilic substitution reaction isto protonate the hydroxyl oxygen with a strong acid in the presence of a nucleophile. The potonated hydroxyl group can now leave as a weakly basic water molecule instead of as a strongly basic hydroxide ion. If the alcohol is primary, the protonated hydroxyl is readily displaced by a nucleophile in an $2 Primary alcohols are commonly converted into alkyl bromides by treatment with hydrobromic aci presence of sulfuric acid. The sulfuric acid serves two purposes: * It increases the amount of protonated alcohol present in the reaction mixture. © Ithelps tie up the water molecules generated in the reaction, shifting the equilibrium to the right, in favor of the alkyl bromide. ction. the ‘The hydrobromic acid is generated in sity by the addition of concentrated sulfuric acid to an aqueous solution of sodium bromide. Possible side reactions: sulfuric acid can cause the dehydration of alcohols and/or ether formation, which lowers the yields ofthe alkyl bromides. of 2-Chloro-2-methylbutane from 2-methyl butanol Write out the structure of the starting materiall Your may think it is @ secondary alky! halide from its name, but it is actually tertiary. Hf the alcohol is tertiary, the protonated hydroxyl-carbon bond fragments to form a carbocation by an Sx1 process, which then reacts with a nucleophile to form a substitution product. Tertiary alcohols react with concentrated HC! to give aiky! chlorides, whereas primary alcohols are inert to concentrated HCI. colts > ec-alol, —> obCobch, Sy ol ooleis WS ls ob cl, cs The mechanism involves three steps: 1. the protonation of the alcohol to create a good leaving group (water) 2. the leaving group departs, forming a carbocation 3. the nucleophile combines with the carbocation to form the product. prep of alkyl halides lecture notes/page 3 of + What Decides SNL or SN2? Steric Hindrance ~ Sx2 proceeds through a backside attack, so the reaction will only proceed if the empty orbital is accessible. The more groups present around the vicinity of the leaving group, the slower the reaction will be. Primary > Secondary > Tertiary Carbocation Stability ~ Since the first step in the Sw1 reaction is the loss of o leaving group to give a carbocation, the rate of the reaction will be proportional to the stability of the carbocation. Carbocation stability increases with increasing substitution of the carbon. Tertiary > Secondary > Primary Overview of Syl and Sy2 Reactions The reaction rate of an Sx2 reaction depends on two things: + How quickly the nucleophile can get in and attach the carbon, How quickly the leaving group can leave. The reaction rate of an Sx1 reaction depends on one thing: * Nothing can happen until the leaving group leaves (the nucleophile cannot get in until the leaving ‘group leaves because the center carbon is surrounded). prep of alkyl halides lecture notes/page + of + Alkyl Halide Classification Tests A. Alcoholic Silver Nitrate If a compound is known to contain a halogen (bromine, chlorine, or iodine), information concerning its environment may be obtained from observation ofits reaction with alcohol silver nitrate. The overall reaction is shown in the following equation: ethanol RX+AGNOs “— AgX + RONO2 The order of reactivity is: s>z>1 b> ‘AgCl —> white ppt ‘AgBr — pale yellow B. Sodium in Acetone Another method for distinguishing between primary secondary, and tertiary halides makes use of sodium iodide dissolved in acetone. The order of reactivity is primary > secondary > tertiary. ‘acetone RCL+Nal meen RI+ NaCl ‘acetone Rr + Nal > RI+ Nase ‘With the reagent, primary bromides give a precipitate of sodium bromide in about 3 min at room temperature, whereas the primary and secondary chlorides must be heated to about 50 deg C before reaction occurs. Secondary and tertiary bromides react at 50 deg C, but the tertiary chlorides fail to react in a reasonable time. It should be noted that this test is necessarily limited to bromides and chlorides. 1° Br > pptin about 3 min at room temp 1°, 2° Cl > ppt after heating 2", 3° Br > ppt after heating 3°C1 > no reaction Note: Nal is ionic, and water will cause Nal to dissolve ond give a false positive, so make sure your test tubes are dry. If you need to heat your somple, don't let the temperature of the water bath go above 50 deg C, oF the acetone will evaporate, giving a false positive test. When the Nal solution is added to the unknown, a precipitate of Nal might occur, leading to a false postive test. Upon mixing, the precipitate of Nal should dissolve if it is not a positive test. ‘Compound Notes ‘Observation tondards 1 -Bromobuiane: Ter 2-Bromo-2-methylburane. 3 Be legend: 2:Bromobutane 2° Br ppt 1-Chlorobutane ra ppt with heat 2-Chloro-2-methyibutane ac yellow 2-Chlorobutone za white ‘no reaction 1 -Bromobuiane Tor 2-Chloro-2-methylbutane ra ‘Synthesis of 2-Chloro-2-Methylbutane Lab Report/Page | of 5 NAME LOCKER NO. DATE SYNTHESIS OF 2~CHLORO-2-METHYLBUTANE LAB REPORT PRE-LAB: ‘SHOW (1) THE REACTION AND (2) THE MECHANISM (WITH ARROWS): TABLE OF REACTANTS AND PRODUCTS [YOU DO NOT NEED TO FILL IN THE SHADED AREAS): ra Produc Mere TamcoNGua CRETE poner {2-methy|-2-butanol) fel (2-chloro-2-methylbutone: ‘MW (g/mole) 28.15 3646 106.59 eles a a i Density (g/ml) 0.805 124 0.866 Yee) v0 25 z You will be performing two washes. Which loyer(s) will be the orgonic layers)? 2. Why do you need to frequently vent the separatory funnel after you have odded the sodium bicorbonate? 3. What isthe purpose of adding Cocizt Instructor’s Initials, Synthesis of 2-chloro-2-Methylbutane Lab Report/Page 2 of 3 RESULTS ‘What was the actual yleld of your final product? 2-CHLORO-2-METHYLBUTANE EXERCISES 1. Determine the percent yleld of your product. (Show all of your calevations) ‘2. What was the limiting reagent? 'b. What was the theoretical yield? & What was your percent yield? . If your yield was low (less than 60%!, explain why you thnk this hoppened. 2. Why can this reaction be carried out at room temperature rather than at elevated temperatures? Synthesis of 2-Chloro-2-Methylbutane Lab Report/Page 5 of 3 3. This isan SN1 reaction. Why does the preparation of 2-chloro-2methylbutone follow this mechanism rather than an ‘SH2 mechanism? Whot isthe RDS (rate-determining step)? 5. Which mechanism(s) feature(s) carbocotion Intermediaries (ree the correct answer}? sNI SN2 cSN1 ond SN2 d. Nether & Compare the syathetes of 1-bromobutone and 2-chloro-2-methylbvtane by completing the following table: ‘-bromobutane 2-chloro-2-methylbutane Time of Reaction Temperature of Reaction (room temp or reflux) What acid wos used os the catalyst? ‘Whet was its purpose (be specific? % Yield Class of Alcohol ‘Mechanism (Sx! or SN2) Prep of 2-Chloro-2-methylbutane/Page 1 of 2 Chem 301 Summer 2016 PREPARATION OF 2- CHLORO-2-METHYLBUTANE The mechanism is Su1. City Hs Hyo—C—cHyCH; 4 HCI ———> te cnc OH a PROCEDURE CAUTION: WEAR GLOVES DURING THE ENTIRE EXPERIMENT 1. Take your 250 mL separatory funnel and stopper as directed to where the reagents have been placed out. 2. Add 10 ml of 2-methyl-2-butanol and 25 ml of concentrated (12M) HCI to the separatory funnel, STOPPER, and take the funnel to your hood workstation. 3. Remove the stopper from the funnel, and swirl the contents of the separatory funnel gently. 4. After swirling for about 15 seconds, stopper and invert the funnel, and vent to release excess pressure. Remember to point the tip of the funnel towards the back of the hood when venting. Gently shake and vent the funnel intermittently for about 2 minutes. 5. Return the separatory funnel to the ringstand. Allow the contents of the funnel to stand until the mixture has separated into two distinct layers. (The beginning alcohol is soluble in HCl; the product is not) Remove the stopper, and drain the aqueous layer into a 250-ml Erlenmeyer flask. Wossh the organic layer with 10 ml of water. Allow the contents of the funnel to stand until two distinct layers form. Again, if two layers do not form, consult your instructor. 9. Remove the stopper, and drain the aqueous layer into your 250-ml Erlenmeyer flask. 10. Wash the organic layer with 10 ml of NaHCO. (Swirl gently for about one minute, without the stopper in the funnel. Then you may intermittently gently shake and vent for about 2 minutes. ) The sodium bicarbonate is neutralizing the residual HC! in this step, which results in the formation of carbon dioxide gas, which must be released by venting. NaHCOs + HCL. ——® C02 ge) + H20 + NaCl 11. Allow the contents of the funnel to stand until the mixture has separated into two distinct layers. 12. Add the aqueous layer to your 250-ml Erlenmeyer flask. 13. Wash the organic layer with 10 ml of H2O. This step removes the residual sodium bicarbonate ‘and NaCl. 14. Transfer the organic layer to a 50-mi Erlenmeyer flask and add anhydrous CaCl2. Swirl the flask intermittently for 2 minutes. Prep of 2-Chloro-2-methylbutane/Page 2 of 2 Chem 301 Summer 2016 15. Decant your product to a previously-weighed sample bottle, appropriately labeled, and then ‘the bottle again, to obtain the weight of your final product. 16. Perform the alkyl halide tests on this product, as well as on the 1-bromobutane you synthesized last lab period. 17. Turn in both products. DISPOSAL Your aqueous layers may be washed down the sink, while Flushing with water. The drying agent remaining after decanting your product can be diluted with water and washed down the sink. Save your product for the alkyl halide tests. After the tests, turn in both products. Alky] Halide Classification Tests Lab Report/Page | of 1 NAME Locker No. DATE ALKYL HALIDE CLASSIFICATION TESTS LAB REPORT ALKYL HALIDE TESTS REPORT DATA SHEET Known Halide Results/Observa ¢ (ppt, ppt with heat, color change, ne reaction) ‘ALCOHOLIC AgNO: TEST ‘Nal IN ACETONE TEST 1 -Bromobutone 1-Chiorobutane 2-Bromobutone 2-Chioroburane 2-Bromo-2-methylbvione. 2-Chloro-2-methylbutone Products 1 -Bromobutane 2-Chloro-2-methylbutane Conclusions Did your T-bromobuane behave similarly to the known 1- bromobutane? Did your 2-chloro-2-methylbutane behave similarly to the known 2- chloro-2-methylbutane? 1. Does the alcoholic AgNOS tes follow an SN1 or SN2 mechanism? 2. Does the Nal in Acotone test follow an SN1 or SN2 mechanism? 3. Which alky!holide would react faster in an SN2 reaction (crele the correct answer}? Why? 1 -bromo-2,2-dimethylbviane 2-bromobutane 2-bromo-3-dimethylbutane 2etbromo-2-methylbutane 1 -bromo-3-methylbutane Alkyl Halide Classification Tests/Page | of 2 Chem 301 Summer 2016 ALKYL HALIDE CLASSIFI ION TESTS. ‘The classification tests for alkyl halides takes advantage of the halo substient and its ability to be displaced. The two tests for displaceable halogen are complimentary; one works best on 3" alkyl halides, while the other works best on 1 “alkyl halides. Thus, by employing both these tests one can possibly differentiate between 1, 2’, ond 3” alky! halides. You are to run two tests on the following compounds: 1-Bromobutone, 2-Bromobutane, 2-Bromo-2-methylbutane, 1-Chlorobutane, 2-Chlorobutane, 2-Chloro-2-methylbutane, and your halide products TEST 1. ALCOHOLIC SILVER NITRATE TEST fa compound is known to contain a halogen (bromine, chlorine, or iodine), information concerning its environment may be obtained from observation of its reaction with alcoholic silver nitrate. The overall reaction is shown in the following equation: ethanol RX + AgNO. ———— —AgX_+ RONO2 ‘wie pet Such a reaction is of the Sn1 type, and a positive test will be the formation of a precipitate. The rate at which the silver halide salt precipitate forms is characteristic of different types of alkyl halides. Tertiary halides are more reac 3n Sx1 reaction than secondary halides, which are in turn more reactive than primary halides. Alkyl bromides and iodides react more rapidly than chlorides, and the latter may require warming to produce a reaction in a reasonable period. These differences are best determined by testing in separate test tubes authentic samples of primary, secondary, and tertiary halides with silver nitrate and observing the results. PROCEDURE. For reagent conservation, test the KNOWN compounds in groups of 3 or 4. Make sure your test tubes are CLEAN. Then, individually, test both of your products. 1. Prepare a hot water bath by heating a beaker of water on your hot plate, in the hood. Choose a size beaker that will comfortably fit your test tubes. 2. Add 1 drop of o known alkyl halide to 20 drops of a 1% solution of silver nitrate in 95% ethanol. 3. Ino reaction is observed within five miautes at room temperature, warm the mixture in a beaker of boiling water (using your hot plate and adding boiling chips to the bath), and observe any change. 4. Note the color of any precipitates; silver chloride i whit, silver bromide is pale yellow, and silver iodide is yellow. 5. If there is ony precipitate, add several drops of 1M nitric acid solution tot, and note any changes; the sliver halides are insoluble in acid. 6. To determine the expected reactivities, test the known halides provided and record your observations. 7. Then test both alkyl halides that you synthesized. Dispose of test tube contents into the Silver Recovery Bottle. Alkyl Halide Classification Tests/Page 2 of 2 Chem 501 Summer 2016 TEST 2. SODIUM !ODIDE IN ACETONE TEST ‘Another method for distinguishing between primary secondary, and tertiary halides makes use of sodium Iodide dissolved in acetone. This test complements the alcoholic silver nitrate test, and when these two tests are used together, is possible to determine fairly accurately the gross structure of the attached alkyl group. The test depends on the fact that both sodium chloride and sodium bromide are not very soluble in ‘acetone, whereas sodium iodide is. The reactions that occur are Sx2 substitutions in which Iodide ion is the nucleophile; the order of reactivity is primary > secondary > tertiary. ‘acetone RCI +Nal ————> RI + NaCI acetone RBr + Nal ————> RI + NoBr With the reagent, primary bromides give a precipitate of sodium bromide in about 3 min at coom temperature, whereas the primary ond secondary chlorides must be heated to about 50 deg C, for up to 5-6 minutes, before reaction occurs. Secondary and tertiary bromides react a 50 deg C, but the tertiary

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