THE ART OF PROBLEM SOLVING IN ORGANIC CHEMISTRY Miguel E. Alonso Department of Chemisey Insite of Scientific Research of Venezuela Caracas, Venezuela AWileyntescenc Publication JOHN WiLEY & SONS New York © Chichester + ne © Toronta + SingaporeTo Adela ond Gabriel tn hs wold, Christiane ad Ramon in the other ‘eytih © 1857 yoke Wi & Sa, eps rm my pu th a 19h Use Seer Copp At et hpi ve copy owrer lc Ret br ‘Seems Deport, Joos Nie Sa ne tra of Congres Catlin Paicatin Das: A Minin pion hE Cris2 Pentig cosi2ate i567 se ao PREFACE "Science doesnot prove anything at all rather it disprove a great del as- sented K. Popper in The Logi of Selec Discovery. This remarkable ought has triggered a consideble amount of philosophical discussion troaghost the ‘wold, and it full meaning may be debuted for several yess. Amoag other possiblities, this sentene implies that scientie discovery is more sly de- ‘eloped onthe bess of the expermeatal negation o disapproving of models or working hypotheses that atempt to explain a given phebomenoa than on the bust ofaBimaton by experiment ofthese model or hypotheses. “The atiudessiciaed with approval i generally recoprized as requiring ‘much les effort than that associated with dissent, because the Ltr implies 2 ‘more complex thought mechanism that nclodes analyse, synthesis, selection, comparison, consrction of opposing standpoint, and clear verbal cmpositon to express and defend the disagreement Therefore, Popp's seatence may also be imerpreted in terms ofa desirable profile fora professional scientist. That is, a person endowed not nly wit high level cognitive memory or eal thik ing, but also with considerable ability for erica hindng, which enables im or hero design hypotheses al expesiments intended to negate existing models. "The ltr quality hasbeen condensed by Howard Schneiderman, Mons to's vice president for research, in a recent college commencement ede (Chemical and Engineering News, June 21,1982), a thee esseatal abies: ‘evelopment of good taste, ability to communicate in clear language, and a rst dal of problem soning eapaciyIris clear hat the stern of scientific edcaton shows inadequacies in at least these tree apects and this lack is curently the eause of deep concern among educators sd theoreticians of eduaton, Of thee thee ails, prot lem solving is probably the most imporant ince i should permit the develop- ment of analytical sil, synthetic reasoning, dscerament in separating the i porn from the unworthy, and the ability t recognize valid saltons fom & variety of allenatives. These qualities help considerably in ataining insight, clevemess, and even anflness and good tase in profesional practice in ca demic and nos industrial environments, ‘The question then becomes, which mechaism thoud we adopt to educate students propery inthis area and thus overcome this deficiency? Thee e 0 unique answer or magic formula. However, 2 good bepinnng tthe itense practice of problem solving in specie areas of Knowledge, although it would be desirable to have amore general syllabus of widespread applicability at est inthe bard core science. And thee Is chemist. Inthe words of Roberus Alexander Todd, beter known as Lowd Todd, “thre is question... that chemistry Is the center point of since" may a tha organic cherie is petaps th hear ofthis cere point because it underies 20 many dieptne, ftom agricultural produc- ton a all levels, biochemistry, industrial chemistry, polymers, phamaceut cals, 10995 ofthe chemistry invelved in all ving systems. Frtermore, the mulitde of mechanisms by which organic compounds undergo transformation ofers an ial platform on which the desible sills mention previously canbe developed, Is the purpose ofthis Book to constrict rom his basi he educational means of achieving the development of problem solving skin the student of advanced organi chemistry. I alo posible tat practi professionals might fad this work useful if ther exposure to problem sli during their college and university studies bas beon inadequate, ‘The use ofa numberof examples that consis the series of S6 problems collected and discussed in the tid chapter was prefered overlong theoretical descriptions, Some necessary fundamen concepts ae concentrated in the it toducory chapters. This book may be found useful ot only as away pide but also as a scuce of interesting and somewhat challenging problems and as ilusrations of reactions and phenomena of general interest T want to express my prattude oll hose who read al or prt of the gh dfs, oferng helpful comment, {am parculasly thankful © Professor Brace Ganem and Professor Jeold Moinwald for heir sofl suggestions ano asl Gasman for hs advice daring the early stages ofthis work [especially wish to thank Mr. Shiey Thomas for her dedicated Production work, Ms. Che ‘Bush for her sdvice on language usige, and to all my students who, over the ‘year, have provided useful feedback for many ofthe Meas expressed in tis ‘work Finally, my thanks wo the Tareawieck family of Lima, Pers. This book Senate geil fom the stimulating end highly caring environment they pro ided while the wing of the fist draft was in progress. Tw9 most amas people contribu the most to this envionment, Don Rafael and my wife, ‘dela MiouRE E, ALONSO