Introduction to the Organic Chemistry - Lab Experiment 3 Grade Sheet | CHEM, Lab Reports of Organic Chemistry

Download Introduction to the Organic Chemistry - Lab Experiment 3 Grade Sheet | CHEM and more Lab Reports Organic Chemistry in PDF only on Docsity! C343 Spring 2008 Results: lePoints earned from the laboratory cover sheet' Pre-Laboratory Questions (14 pts.) Points awarded for the pre-laboratory questions. Condensed Procedure (4 pts.) Results: (3 Cleanliness (10 pts.) Point Value Standards 4 Procedure is concise and includes proper use of appropriate terminology for the experiment. All quantities of reactants are presented with proper units. Experimentalist familiar with organic laboratorv techniques could easily replicate the experiment. 3 Mostly complete per the highest standards, but either incomplete (missing an element) or has two flaws in the criteria set-forth in the highest standards. 2 Mostly incomplete: three or more missing elements from the highest standards. I Incomplete; lacks details, and / or procedure is too verbose. A.l. Notes: Results. + Lab Report: Introduction (a pts.) Point Value Standards 4 Objective of the experiment is clearly stated. Contextual background of the experilnent is presented in a logical fashion that flows into the objective of the lab. Flow of the introduction is well organized and the length is suitable for the experiment. Proper citations are given. 3 Mostly complete per the highest standards, but either incomplete (missing an element) or having two flaws in the criteria set-forth in the hiehest standards. 2 Mostly incomplete: three or more missing elements from the highest standards. Lacks flow of ideas into a nroper obiective. I Incomplete; presenting a minimal amount of background information, incoherent understanding ofthe experimental purpose, relationship of experiment to context, or concept of experiment. A.l. Notes: Results: ll t)-, Page 1 of3 Lab Report: Experimental (4 pts.) Point Value terminology for the experiment. Exact quantities of all proper units. Experirnentalist familiar with organic for the appropriate experiment (yield, m.p., b.p., NMR, etc. Mostly completeper the highest standards, but either incomplete (missing analytical data) or having two flaws in the criteria set-forth in the hiehest standards. Mostly incomplete: three or more missing elements from the highest standards. Incomplete; lacks details, and / or procedure is too verbose. A.l. Notes: i i n /^\ I \Ae\u':^'-l' >'*\)u \2,. o,-',^ >a.*?G Lab Report: Results / Discussion (15 pts.) Lab Report: Conclusion (3 pts.) Point Value Standards t5 Logical progression ofresults supported by data to address objective ofthe experiment. Appropriate tables, figures, and schemes are presented to suppoft the discussion. Theoretical arguments are used to support analysis. Conclusions demonstrate a logical assessment of the data and relevant arguments are presented from the most impofiant to the least relevant. Proper citations are included. t2 Mostly complete per the highest standards, but either incomplete (missing an element) or having twoflaws in the above elements. 9 Mostly incomplete: three or more missing elements from the highest standards. Lacks flow of ideas into a proper conclusion. 6 Incomplete; presenting a minimal analysis or improper support for conclusions. A.l. Notes: Ho., ecu*rf,U. @ Lf cw g,Alor'tarJ;; Results: l2 Point Value Standards 3 Conclusion fully addresses the question and /or objective of the experiment. Conclusion is concise and completes the report by answering the contextual question. 2 Mostly complete per highest standards, but either incomplete (missing an element) or having two flaws in the above elements. I Incomplete; presenting a minimal conclusion or not properly contextualizing the conclusion back tothe obiective of tle experiment. A.l. Notes: Results: 3 Page 2 of 3 EI; lra.^11/\l isli\t.,V'r^ aF?.r*h, t Ll/crwra r*-')<-< cli? *&**' ,r"rY'clrP 's:\r 'fuf+'" r::;Lr ,-rJ^* v'*-J/A 5) (r*olr.,,-"1 Di slitt*hvn ftyn-'.\-s ll,nPra'nuta* &*( dt7 CarJzn*r ;.rhvhtl ult* t+p onF N0TE: INSERT PERI0DIC TABLE UNDER C0PY SHEEI BEFORE WR|T|NG.IllE HAYDEN.McNEIL STUDENT LAB }|OTEBOOK 7^ O(PERIMENT/SUBJECT DATE 03 Mrvre LAB PARTNER LOCKER/DESK NO. COURSE & SECTION NO. D) pbki", a to^l ru,^{-b.Ho* WP, a- &irHltJ'.>*S , ceta-A,r*ttel., 6cuu--to) di.<{ir\a hr^ a-r--pkr a-; y*);&, ;*t* *,irii"+ ,* -*rlVo-n{- r. Yn clo* a4onll^ {o porifr>* ,f 6rb 6L41r*'n*-- bu' 'S?'*l .rS Wdttd^t\1,rrkt nr\r\".e i,t$ /co'*l dut{-b."#,t* fI-"A, ca.re.$.11rar^-d a.Ad L4 b,lat &i;Ps. Po r* a.&d ta€it"^A crdp: &o hr+- ,2ll&^ ! Per"g,^,*'+ brLI2 {-{osZ b np,co-o'fu| , h,-*ve Al U,-d q*rr^ 6'vd {-"'^ rt^'"r:t*-+- low\"ot t" b, 14o, sord s* t"".*i> i^.b ru"os\^* t ,nr+ J't^t' '*tl ! D\t+itt a{ v*\e dt t-L J'uPs [a,r +ccond, Dilfitt ua}',\ 5ou k-^vc L ,.,*l Et Jis{-ill.a,{e. Po ,uo* d;chrl ail liSuiJ €'.'*- 16o u*\ Caaay 1 N.rl-,*,JaU 1-*c*iu^4 {i<k'ttc.h'"* oFpa.ro,t",:. Ogto';q So ,n-l *k'-'^",1 -ua'+vr bA^V\"..r- 1 *&L k |eo ,*t ruu.J bofue.u- C(o..K, ^.# z-t bo;l;7 chir>s c.^-6 dt rl.\\ . p., r i [i cJi o " {- ld e^f"\ *l'or ^ ,} JnV^n ,'-rt g[f*iw rAo\ "\ rrwk n 4).^ h'XuiL ,vt.,tor| W c.&- h.^,.Lcr I a.wf delor,^*\ JH '+ li1uid in ,'ia,\. 54 P'-!.,y lt\uil ;x,fr> pr{- Q|r',st o ,ry a,ral7 li c<f 6 **,[ I bi I t ; tt &*] raco r{ L^pa'.-,t*t ' n '- *,,,\' a& dill ttu,tt c.otlzc.kl r 54 d.irfi4a-H"r otJe; lo *lter ery L i5 obh,;,,-oj , $le^Ic,r %t"titig Tes* P\a& aA"*l l,j ^,1 oP wo.,k'v i"" l'.rf +-tc , osiV 4 V*tk* Ptfrcflt a^C *ofio\ b.rlb ab[z,ir.. { inc( o* or&**q , kl*rr. l1*t4w."'t* J*'P I d-ap -J ob*,rw iwLarz-clfons. SIGNATURE OATE wlTt{Ess/rA DATE N0TE: INSERT PERI0DIC TABLE UNDER C0PY SHEEI BEF0RE WRITING .IHE HAYDEN'McNEIL STUDENT l-AB N0IEB00I( Plot of Temp vs. Distillate for Simple Distillation 105 100 95 90 80 75 70 60 10 15 20 25 Temp ("c) Volume Distillate (ml) Distillation. Uncertaintv in an Organic Chemistrv Laboratorv Experiment Introduction: There are many situations in the world where distillation techniques or those similar can come in handy whether it be in the research labs of chemists or in other fields of work that require purification of a particular liquid compound. Distillation is often a technique used in the final purification of a liquid compound with 2 liquids of different boiling points. Distillation works by the formation of vapors and subsequent condensation of those vapors in the attempt to isolate the lower boiling point vapors at the top of the distilling column. The techniques and efficiency of simple and fractional distillation will be explored in this lab as well as the effects of an azeoffope on distillation techniques. The second objective is to use distillation and crude qualitative tests to ' (') determine the identity of an unknown liquid. V.lr (zx- Experimental: Distillation and Identification of an Unknown Mixture of Liquid After a simple distillation apparatus was assembled an unknown mixture of liquid (H) was obtained and the volume measured was 24.5 ml. Unknown H was then poured into a 100 ml boiling flask using an analytical funnel. Several boiling chips were added to the boiling flask. The boiling flask was reconnected to the distillation head and a heating mantle was raised up to the boiling flask. The control knob on the rheostat was turned to the 4. The temperature reached 650 Celsius and about 2 ml of forenrn was collected in a 125 ml Erlenmeyer flask. The Erlenmeyer flask was replaced with a graduated cylinder and the temperature (boiling point about 660 q was recorded for every 2 ml of distillate that was collected until 10 ml of distillate was collected (Do not distill all of the liquid from the boiling flas$. The distillate was collected at approximately 2 drops of distillate for every 3 seconds. Water Solubility Test and Oualitative Density Tests About I ml of water was placed in a test tube. Using a Pasteur pipette and a suction bulb about 2 inches of unknown H was drawn up into the tip of the pipette. The tip of the pipette was immersed in the water in the test tube and the unknown distillate was squeezed out drop by drop. The interactions between the water and the unknown H distillate were observed. Two more tests were performed in the same manner using ethanol-water in a 4-l ratio (1 ml) and l-1 ratio (l ml) proportions. Results and Discussion: Table 1: Group Data for Simple Distillation of Methanol-Water Temoerature oC Volume (ml) Averaoe Grouo 1 Group 2 Grouo 3 Grouo 4 2 76 X 73 78 76 4 77 X 75.5 79 77 6 77.2 X 73 81.5 77 B 78.5 X 76 82.5 77 10 BO X 79 B3 7B L2 82 X 81 84.5 80 t4 B5 X 85 B6 B3 16 88 X 89 8B 87 18 92 X 93 88.s 94 20 95 X 9s 91.5 98 22 96.5 X 97 93.s 99 24 9B x 9B 97 100 26 99 X 9B 99 100 28 X 99 Table 2: Group Data for Fractional Distillation of Methanol-Water Temuerature oC Table 3: Group Data for Simple Distillation of Acetonitrile'Water ture oC r Volume (ml) Averaqe Grouo 1 Group 2 Group 3 Group 4 2 70 X 74 66 X 4 73 X 79 67 X 6 74.5 X B1 6B X B 76.5 X B4 69 X 10 77.5 X 86 69 X t2 82.5 X 100 65 X t4 81.5 X 100 63 X 16 81.5 X 100 63 X 18 99 X 100 9B X 20 99.5 X 100 99 x 22 100 X 100 100 x 24 100 x 100 100 x 26 100 X 100 100 X 28 X x Volume (ml) Averaqe Group 1 Grouo 2 Group 3 Grouo 4 2 7B X BO 75 7B 4 78 X BO 75.6 78.5 6 79 x B1 76 79.5 B 79 X B1 77 BO 10 81 X 82 78 B1 t2 B1 X B3 78 82 L4 B3 X 87 BO 81.5 16 BB X 92 81.5 B5 18 98 X 100 95 100 20 99 X 100 96.5 100.5 22 99.5 X 101 97 100.5 24 99.5 X 101 97 100.5 26 100 X 101 9B 28 X 100 liquid and vapor states have the same mole percent composition at the boiling point of the distillate (Johnson, 2008). Since an azeotrope forms before all the distillate is collected any frrther distillate collected is most likely not going to be in the pure form that one had wanted to obtain. This may make it harder to obtain an accurate result when trying to determine how much distillate was present in the original solution. The approximate concentration of distillate present in the original liquid mixture was calculated by finding the inflection point in the graphs of temperature versus distillate collected and doubling the determined value. For the acetonitrile-water mixture it was determined that the original solution was32%o composition acetonitrile (32 ml acetonitrile for every 100 ml water) and 68% water. For the methanol-water mixture it was determined that the original solution was 38% composition methanol (38 ml of methanol for every 100 ml of water) and62o/owater. According to the distillation of unknown H the boiling point was 660 C. Based on boiling point alone the possibilities of unknown H were: (Z)-1,2-dicholoroethene, 2- methyl-l-pentene, 2-methylpentane, l-hexene,2-ethyl-l-butene, 2-methylfuran, trans-3- hexene, crs-2-hexene, hexan, (E)-3-methyl-2-pentene, 1 -bromopropane, methylcyclopentane, or (E)-1,3-hexadiene. After the water density test was performed it was determined that unknown H was less dense than water and was insoluble in water. B as ed on thes e ob servation s (Z)- 1,2 - di cho loroeth ene, 2 -methylfu ran, and l-bromopropane could be ruled out. Further tests were performed and it was also determined that unknown H was less dense than both methanol-water (4-l proportion) and methanol-water (1-1 proportion). Based on these final2 crude tests unknown H was determined to be trans-3-hexene because cis-2-hexene has a slightly higher boiling point \,.1 ' aY ,[" ko^ont A"f,^rI t.? ! 1', and the cis conformation causes there to interactions between the cis branches. be a slightly higher boiling point due to In conclusion, the experiments performed have insisted that fractional distillation is indeed a more effective way to separate two liquids with boiling points differing by less than 600 C and that simple distillation, even though it works, is not the preferred method unless the two liquids differ by more than 600 C. Through the distillation of unknown H and the crude qualitative tests performed, the best fit molecule for the unknown w as tr ans -2-hexene. References: Johnson II, David C. Oreanic Chemistry Laboratory C343. Spring,2008. Mohrig, Jerry.Hammond, Christina. Schatz, Paul. Techniques in Organic Chemistry, 2nd Edition . 2006. U C) u CB (Da E c) F 02 4 6 810t2t4 161820222426 Volume (ml) 28 30 32 34 36 38 40 42 44 -66-