a&&.& 4 CHEMICAL EDUCATION R - w S Report of the Organic Subcommittee of the Curriculum Committee, Part II In the previous report1 the Organic Subcommittee described two outlines (Topical and Principles) delineating approximately 80% of the course content of a "standard" two semester organic chemistry course. Also included as a sample were the performance objectives for Section X, Alcohols and Ethers, of the Topical Outline. The sets of performance ohjectives for both outlines have now been completed and will be made available (together with the outlines) in a separate publication of the Curriculum Committee. Notice of cast and availability of this publication will he made in this Jour""1 ....
The coniiderahle time and efhrt spent on this project has clearl y indiesled that on the whulc teachers oforganic chemistry clearly agree on uhat is imuortant in the discipline and this is reflected in a-rather high degree of consistency in-course content. This eonfidenee and claritv. in DurDose leads to a relativelv stable situation w ~ t hrespect to changes in prvrtice nnn philuwphy. \Ye lee1 that underdraduate organic chemistry rducation i< in nn excellenr state of health. Nevertheless, even with this curricular stability there is evidence for a willingness to change in response t o changes in the development of the basic knowledge of the discipline. Certainly our decision to prepare two sets of outlines and performance objectives arose from a recognition of a general trend from a course organized accordine t o functional erouos t o an oreanization disolavine more concern ior basic principles J i n w this dual emphasis i.; likply to cmlinur fur the foreseeable future i n i t r w t ~ r sma" wish to use the subrommittec'r malerials as a guide to prucerding along tilher ap. proach or to producing an integrated approach consistent with individual tastes. The subcommittee makes no recommendation as t o the desirability of either approach. The question will probably arise as to what differences, if any, exist between the two sets of performance ohjectives. A eomparison leads the subcommittee t o the minion that there is a eonsiderahlr drgrre of intenhangcalAily The pcrfurmance objectives for the Topical Outline deal uitn specifically r t ~ r e dreactiunr and ex. plnnstims of phenomrnn while those f8,r the I'rinriples Ourline require n hroadcr scope and toromr extent n greater depth of undersrandmg of the auhleet matter. The perfurmnncc oblectives of the Pmcivles Outline call fur greater interpretwe rklllr uhtle thme for the ~ d p i c a Outline l seek more direct r&ponses to explicitly stated situations. In order t o allow comparison of the two approaches, we have included here the outline topics and performance objectives for a specific topic: acid-base concepts. Each outline topic is immediately followed by the corresponding performance ohjeetivek). I t is interesting to nate the varying sources of the topics and performance objectives in the topical approach. While a detailed comparison is left to the readers, in general, the performance ohjectives for the Tooical Outline tend to consider the acid and base orooerties of the functional groups and not the concept of acidity and basicity emphasized in the performance ohjectives for the principles Outline. Another area of subcommittee interest is the organic laboratory program. In order to define present practices and philosophies and t o provide instructors with information helpful in new program development or ongoing program reevaluation, the subcommittee plans t o produce a laboratory outline with accompanying performance ohjectives. To this end we have prepared and distributed a questionnaire t o approximately 1,200 two- and four-year colleges and universities in the United States and Canada. This project will be completed by the 1976 Fall ACS Meeting a t which time the results of the questionnaire and project will be made available. We welcome suggestions, comments or questions concerning either the lecture or laboratory projects. Such communication should be directed t o the chairman, Leroy C. Butler, Chemistry Department, Windham College, Putney, Vermont 05346.
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Subcommittee Members l r m y C. Butler, Chairman, Windham College Stanley C. Bunee, Past~ehsirman,Rensdesr Polytechnic In~tifute K. A. H. Adsma, Mount Allison University R. J. A,,% Lehigh County Community College M. W. Cmnyn, Reed College T. W. CuWhsll. Indians Univerrity-Purdue University D. B. Denney, Rufgprs University R. W. Gleason, Middlebury College S. C. Hmpr, PennsylvaniaState University. New Kensington Campus P. L. Kum1er. Saginaw Valley College 1. Mareelli. Hudson Valley Community College W. S. Mungall. Hope Cn11cge B. E. Norcross. SUNY Ringhamton A. Silveira, SUNY Oswego F.B. Slersk. Ma,eer county community College G. W. Smith. Univer~ityof Alaska S. D. Squibb, Univedry of Nunh Carolina-Asheville J. Vilin, Corning Communitycollege E. J. Welsh, AlleghenyCollege C. Westherbee. Millikan University L. E. Weller. University of Evansville
Section of Prlnclples Outline a n d Corresponding Performance Objectives Pertaining t o Acid-base C o n c e p t s A. Br*nated-Lowry fhmry of adds and bases, acidity and baaicity in "on-aqueou. system%free energy and the equilibrium mnsfsnt. rates oipmton tcanafd Performance Ohjeniuer 1. Compere the effect of solvent on the acidity ofprotic acids. 2. Write the equilibrium constant e i p r e ~ i o nfor the ionization standard of an acid or bsse and relate the magnitude of K to the free energy change, A m . .
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3. Clauifyrster of proton transfer ofvarious protr acid&
B. Lewis acids and bares2 Pcrfomanee Objective 1. Define the Lewis stid-base syatem and write illustrative reaction% C. Resonance, inductive, entropy, and sterieefieefs on acidity and basicity Performanee Objpeti~ei 1. By means of examples show how the acidify or orgsnie adds b affected by the intrdudion oisubstituonfs. 2. Give an example of steric inhibition of resonance which leads to enhanced basicity ofan aniline. 3. Explain the change in basicity of the neries a nitrile, iminc, and an aliphaticamine in terms of hybridization changes.
D. Acidity of mvslent hydrogen compounds-hybridilatiii, e.g., in esrbonyl, nitro. eya""eompound~ Performanee Ohieetiver
active methylene,
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' J. CHEM. EDUC., 49,761 (1972). % I fnot included in earlier courses.
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by writing resonsnee aructurer of thederived anions. 3. Explsin the change in acidity a i tho a oxygen-hydrogen bond in a1eohola, phenols and carhoxylie acids.
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Write exprersiona for the keto-end tautomerism for the mmpaunda phenol, 2.4-pentanedione, seetone: identify the predominant iorm in each ease: and acmunt for its re dominance.
Sections of Topical Outline a n d Corresponding Performance Objectives Pertaining t o Acid-Base C o n c e p t s VI. Alkynes C. Acidityand preparation of heavy metal salts Performance Ohjecfiii 1. Explain the inenancd acidity of acetylene relative to ethylene and give a spoeifie example of the synthetic utility of this enhanced acidity.
IX. organometallieeompound~ B. Grignard reagents: solvent, maelions with active hydrogen compounds. Oz, C01
Volume 53,Number 1. January 1976 1 25
Performance Objmtive 1. Anange the follouing in order of increasing acidity: watt., methanol. methane, benzene and scetyiene X. Aleoholsand s t h e n D. Rcaclidns of almhols- O-H bond acidity, HX reactions, ester8 with nitric, aulfurie, and phosphoric acids, dehydration, and sfher formation P~rformanceObjeetive 1. W r i e equations (o .how the overall mume of the madona of aimhole with a. d h l i metals
XI. Aldehydesand ketones H.Helogmstion of ketone*: mechanism of aeid and base catalyzed enoliution. haloform reaction Performance Obaefive 1. write the neeepted mechani.ms far the aeid and bsve eatalyzsd .norhation of aldehyde, and ketonesand apply these to hsiogenation and denb r i m exchange. XI1 Cmborylie acids and darivativea
B. Dissociation: earborylete ion resonance stabilization, inductive and entropy afhef on acidity Perfomance Objective 1. Explain the basis for the acidity of earborylic acids and diacus tho lac(onwhich effect the relative acidity of earborylic acid*. XV. Aminea and related m m p u n d s
B. Acid-bas. hehsviorof aliphatic amincs. aromstie aminos, amid- and imide Perfmmmce Objectivee L. c o m p r e the relsfiv. basicities Of aliphatic sminea, ammatie sminss. ammonia, amidas,snd nitriies. 2, Indicate the e1eeuonic and M r i e factors affecting the basicity of amines. XVI. Aminoscida, peptidesand pmteins
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Performance Ohjsdiven 1. writ. atrudur.1 formulas for three amino acids obtainable fmm protein hydrolysisuhcn these aminoaeida rue placed in a q u w u aolutionsaf low pH, high pH, and at the p H of thsir isaieevie poinr*; in addition, exoldn uhv it is that their e d v . l c n t weiahrr cannot b. obtained by aim-
XVIIl. Substituted ammstic mmpoupodd D. Alyl wlfonie aeida and d c r i v a t i w chloride., amides and sulfonates, strueture and acidity. leaving g r o u p Performanee Ohjoetiue L. compare the .ractivity of (a) l~lfoni"vith earboxy1ie acids and (b) the derivatives of these acids.
E Aryl oxygen mmpounds: ryntheai. of phenols from awl halides and livllonie acids, acidity, dkylolion and d o t i o n reacfioru ol phenol, Clairen marron*emont
Performance Ohj~efivs I . Compare and amount for the observed acidities of phenole, earhorylie neidr and almhol. XXII. Organiesdfurmmpovndli A. Preparation, phy3ieal and ehsmiell1 pmprties of sulfur anaioga of common oxygen containing funetianal groups. (RSH. RSR. RSSR. DMSO, RSO1OH) Perfrnan~oobjactive 1. Compare the hydrogen bonding propertis* and ~ K values A of aleohols and mercaptan. and describ. the effect3 of these differences on boiling solubilifi.r, and nucl~ophiliepropniee.
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3 Sections in italics me considered highly desirable but not essential.
