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NATIONAL COOPERATIVE UNDERGRADUATE CHEMICAL RESEARCH PROGRAM ETHALINE CORTELYOU A m o u r Research Foundation, Chicago, Illinois
W. P. CORTELYOU Roosevelt University, Chicago, Illinois
T H E National Cooperative Undergraduate Chemical Research Program (NaCUR)
(1) stimulates undergraduate research interests (2) determines and collects some data missing from the published chemical literature (3). enables teachers of small schools to pursue research programs (4) offers industry an opportunity to cooperate with colleges in encouraging students t o stay in chemistry. NaCUR enters its ninth year with one project from a foreign country listed, number 21 directed by Dr. Y. Marcus1 of Israel. All but four of the project directors are chemistry teachers. For the 1956-57 school year NaCUR offers 21 projects for student participation. The outline used for each project is: (a) (b) (c) (d)
typical unit assignment special equipment needed special chemicals needed minimum student prerequisite ( e ) name and address of director. ANALYTICAL PROJECTS 1. Quanlized Qualitative Analysis: a New Approach to Systematie Qualitative Analysis (a) Determine the number of milligrams (in solution) of each of a group of cations required to give a oharaeteristic reaction with 1.0 ml. of each of several different reagent solutions under specified conditions. ( 6 ) Twenty-four small reagent bottles (30-100 ml.) with droppers in the stoppers, or any convenient means of counting the drops of solutions used. (c) Salts to prepare the cation solutions. Sometimes special organic reagents. ( d ) Carnuletion of a course in systematic qualitative analysis. ( e ) W. P. Cortelyou, Roasevelt University, Chicago 5, Illinois. 2. The Importance of Some Simple Quantitative Techniques and Emws (a) Single deflection weighing. ( b ) Usual instruments and equipment needed for gravimetric quantitative analysis. ( e ) Quantitative analysis. ( e ) Ethaline Cortelyou, Department of Chemistry and
Address until June, 1957: The Royal Institute of Technology, Stockholm 70. Sweden.
Chemical Engineering, Armour Research Found* tion of Illinois Institute of Technology, Chicago 16, Illinois. 3. ClassifLeationof Cations Based on Qualitative Chromatographic Separation by Means of Spen'fre Solvats (a) Determine the Rr values for a group of cations employing as solvents specified mixtures of two ale* hols diluted with ( a ) water and ( b ) acetic acid. Keep temperature, cation concentration, and development time constant. ( b ) Sheets and rolls of Whatman filter paper prepared for paper chromatography. Wide-mouthed jars or bottles. 12-15 inches tall. are useful. ( e ) Salts to prepare cations. Solvent solutions, e. g., acetic acid, sulfuric acid, butanol, isopropanol, and other alcohols, if desired. ( d ) General chemistry and some qualitative analysis. (e) Sister Mary Alice, Associate Professor of Chemistry, Mount St. Mary's College, Los Angeles 49, Cslifornm. 4. The Development of Quantitative Volumetric Detemination of Paint Pigment Constituents (a) Compmison of five assigned internal indicators for the titration of zinc. ( e ) Special indioators assigned. ( d ) Quantitative analysis. (e) Clovis Adams, The Sherwin-Williams Company, 115th Street and Cottage Grove Avenue, Chicago, Illinois. 5. The Detection of Ions bv Differential Diffusim ( a ) To devise methods for detectine the mesenee of anions and cations bv their different ra&s of diffusion in gelatinous media, such as concentrated gels of gel* tine or polyalcahols. ( b ) Petri dishes, watch glasses, and reagent bottles with droppers in the stoppers. ( e ) Salts to prepare ionic solutions and developers; also organic reagents. ( d ) General chemistry and qualitative analysis. Marvin Antelman, Research Director, Marantes Lab(e) oratories, 7 South Cambridge Avenue, Ventnor City, New Jersey. ~
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INORGANIC PROJECTS 6. Solubilities of Inorgank Sulfamotes in Water ( a ) Determination of the solubility of barium sulfamate in water at 20°, 30", 40°, and 50°C.; includes preparation and purification of the barium sulfamate. ( b ) Screw-capped bottles of approximately 125-ml. csr pacity; suitable shaking device for six or eight bottles in a thermostat. ( e ) Reagent grade sulfamic wid. ( d ) Good background in quantitative analysis. (e) Sister Agnes Ann, Immaculate Heart College, Los Angeles 2, California. 7. Solubililies of Inarganic Halides (Other Than Fluorides) in Organic Solven2s
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(a) Determination of solubility of lithium bromide in nbutyl alcohol a t 0°",25", and 100°C. (b) Constanttemperature bath; screw-capped glass b a t tles of approximately IO(t125 ml. capacity; shaking device. (c) None other than good grade solvent and solute. (d) One quarter of quantitative analysis or a t least be pursuing same. (e) Kirby E. Jackson, University of Alabama, University, Albama.
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ORGANIC PROJECTS Condensation of Aminoaeelonilrile with Vamr?m8Ketone* to Yield the Corresponding Schip's Bases fb) Usual organic chemical equipment. (d) Elementary organic chemist.^. (e) Edward Ronwin, Department of Chemistry, Mount St. Mary's College, Los Angeles 49, California. 9. Preparation and Charactcriration of Diamides fm Methylene Bis(4-phenyl isoeyanute) and Alkyl or Awl Bromides Through Ihe G~ignardReaetion: 8.
-
15.
-
CH,(C)-HCO)~ + 2RMgX (Then HCI)
H
C
10.
11.
H
0
+ 2MgXCl
~ -k-A-R)2 ( ~
(a) Condensation of the RMgX compounds of three or four alllkyl or aryl bromides with methylene his-(& phenyl isocyanate) and subsequent hydrolysis to the diamide, methylene bis-(pacyl aniline). The purification of the diamides and determination of physical constants. (b) Two-neck, round-bottomed flasks. (e) Methylene bis(4phenyl isocyanate), alkyl or aryl bromides, metallic magnesium far Grignrtrd reagents, dry ether. (d) Elementary organic chemistry. (e) Roy G. Bossert, Ohio Wesleyan University, Delaware, Ohio. P~eparationand Properties of Acylaeenaphthenes (a) Preparation and properties of 5-(p-toluy1)-acenaphthene. fbl General orpanic lahoratorv eouidment. (cj ~ c e n a ~ h t h & , ptoluyl "chloride, carbon disulfide, hydroxylrtmine hydrochloride, phenylhydrazine hydrochloride, etc (d) Organic chemistry. (e) Edith J. H. Chu, Immaculate Heart College, Los Angeles 27, California. Charaeterizatia of Amines as Salts of Ozalic Acid fa) Pre~arationand crvstalliaation of desired salt8 and , determination of melting points of these derivatives. (b) Good standard thermometer. (c) Primary amines. (d) Two semesters of organic chemistry and preferably a course in qualitative organic chemistry. (.8 .) Harrv Cohen, Roosevelt University, Chicago 5, ~llfnois. Preparation of Certain Schif Bases and Their Reduetion with Lithium Aluminum Hydride (a) Synthesis of octadecylben~ylideneamineand reduction t o N-oetadecylbenzylamine. (b) Three-neck flask, mechanical stirrer, Claisen flask, and, for most preparations, a vacuum pump. (c) Lithium aluminum bydride. (d) Elementary organic chemistry. (e) Bertin L. Emling, St. Vincent College, Latrobe, Pennsylvania. The Reaction of Phenols with Activated Aryl Halides
.
~
12.
13.
~
(a) The product of phenol, 2,4dinitrofluarobenzene, and a tertiary amine catalyst is isolated and purified. The melting point is the physical property sought. (b) Ordinary laboratory apparatus. (e) A series of phenols and 2,4dinitrofluorobenzene ( E a s t man or Matheson). (d) Organic chemistry. ( e ) John D. Reinheimer, The College of Wooster, Wooeter, Ohio. Synthesis of Polynuclear Thiaphene Compounds (a) Synthesis of 2,5-dimethylbenzathiophene. (b) St,andard organic equipment, such as vacuum pump, chemical stirrer, and three-neck flask. (c) pThiocresa1, lithium metal, chloroasetaldehydc, diethylscetd, and dimethyl sulfate. id) , . Oreanic ehemistrv. ( e ) F. G. Bardwell, Chemistry Department, Northwestern University, Evanston, Illinois. The Charaeteriratim of Phenols as Their 6,4- and 5,4-Diehlorobmoates (a) Preparation and purification of the various phenyl esters of 2 , 4 and/or 3,4-diohlorobenzoic acid by esterification of the ~ h e n o l s with the diehlorabenaoyl chlorides. (b) General organic laborntory equipment including an accurately calibrated 360PC. thermometer. ( e ) 2 , 4 and/or 3,4dichlarobenzoyl chlorides (Eastman), a aeries of phenols, anhydrous pyridine, methanol, and ethanol. (d) Elementary organic chemistry and a prior or cancurrent course in qualitative organic analysis. ( e ) Robert G. Johnson, Xavier University, Cincinnati 7, Ohio. Synthesis of Bromohydrins ( a ) Reaction of olefins with N-bromosuccinimide in water. (b) Three-neck flask, stirrer, and, in same instances, a means to reduce pressure during distillations. ( e ) Olefins and N-bromosuccinimide. (d) Organic chemistry. (e) Cyms 0. Guss, Department of Chemistry, Colorado A. and M. College, Ft. Collins, Colorado. Preparation and Characterization of Substituted Diary1 Thioureas (a) Prepartration and identification of diary1 thioureas, with a substituent (CI, Br, NOs CH3, OH, ete.), on both or only one phenyl nucleus in different pasitions (o, rn, or p). (b) General organic laboratory equipment. ( e ) Aryl amines, aryl isothiocyanates, carbon hisulfide, and common organic solvents. (d) Completion of course in organic chemistry and quantitative anslvsis. ( e ) J. F. Deck, ~ i i v c r s i t yof Ssnta Clara, Senta Class, California.
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17.
PHYSICAL PROJECTS
18. Determination o j Ref~artiveIndezes of Binary Liquid Miztures at Various Conmztrations and Va7im.i Temperatum9 (a) Determination of refractive indexes of dioxane-ethyleue glycol solutions of various concentrations a t some given temperature. (b) Good refractometer, constant-temperature water bath, circulating pump. (c) The liquids t o be used. (d) Elementary quantitative analysis and elementmy organic chemistry. (e) R. I. Rush, Centre College, Dsnville, Kentucky. 19. Determination of the Reliabilitg~.of Ideal Lows i n Typical Pmctieal ~&umstances (a) Determination of the molecular weight of naphthalene ~
~
296 from its freezing point depression in benzene at several concentrations to observe departure from ideality as a function of concentration, (d) Physical chemistry. (e) Nathan Yagol, Roosevelt University, Chicago 5, Illinois. 20. Chemical Means of Cleaning Ultramicro Pipets George F. Hand, State Microscopical Society of 11(e) linois, 7512 Olcott Avenue, Hammond, Indiana. 21. Anion-exchange Constants for Thiocyanate Complezes ( a ) Determine the distribution of a given metal between an anion-exchange resin and an aqueous solution, containing a constant concentration of the metal (or thiocyanate), and varying concentrations of the thiocyanate (or the metal), when a certain weight of resin is shaken with a certain volume of the aqueous solution. Shaking machine, flasks with ground glass stoppers, usual quantitative analytical equipment (a colorimeter is helpful). Anion-exchanee resin. Dowex-1. 100-200 mesh, X-10. id) Quantitative analysis and, conburrent with research, physical chemistry. (e) Y. Mmcus, Weizman Institute of Science, Rechovot, Israel.
JOURNAL OF CHEMlCAL EDUCATION
50 hours of work for completion of any library search needed, the laboratory work, and e research report. Ordinarily the same assignment is made to two or more students, independent of and unknown to each other, in different schools. Each student works under the direct supervision of his own teacher. When a teacher decides a student has completed an assignment, he supervises the preparation of a research report to be submitted to the National Project Director. Each National Project ~ i r e c t o sets r his own criteria for accepting or rejecting a report; often acceptance is based upon the checking of results obtained by two or more students. A Certificate of Acceptance is awarded to each student submitting an acceptable report. Each certificate is signed by the student's teacher, the National Project Director, and the president and secretary of Handbook Publishers, Inc., which furnishes the certificates. Suitable data may be selected for publication in the "Handbook of Chemistry." A National Project Director may publish data obtained on one or more assignEach of the 21 National Project Directors directs the ments as a paper, giving full credit to participating research on his project by issuing an assignment to each students, teachers, and schools. Any teacher or industrial chemist interested in directstudent participant through the student's teacher, a Local Project Director. Any teacher having a student ing a new project should write to one of the authors as interested in a particular project should write directly soon as possible, since a project is listed under the dito the National Project Director for an assignment. rection of the first person to request it. An outline of a Each project is subdivided into assignments, or re- project for the 1957-58 school term must be sent to search units; each assignment usually requires about one of the authors by January 10, 1957.
