An organic "reaction" (author response) - ACS Publications

In contrast, I remember my heart thumping as I initiated my first Skraup reaction in the basement of our house. In a prearranged scenario I hurriedly ...
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reallv have the faintest idea how this can occur. Instead of consiant attention tothedistance between the flameand the flask relative to the position of the front of condensate, they stand around horedkatching distillations on automatic. even tell the students the proper Variac settings for the mantles. In contrast, I remember my heart thumping as I initiated my first Skraup reaction in the basement of our house. In a prearranged scenario I hurriedly put out the propane hurner, unscrewed the clamps, and plunged the 500 mL roundbottomed flask with its violently boiling, black mixture into a bucket of snow and water to moderate the charcteristic, sudden exotherm. I t wasn't very intellectual, I suppose, but I was on mv wav to making a potential anticancer agent. I felt it a worthwhile activity in addition to being enorhous fun. 'I'hedrur companies now design magic bullets with computers, hut they will require someone with the requisite finger skills to synthesize whatever molecules they design. Like farmers, organic chemists will always he needed if not respected. I sense that Pickering's comments about the organic lab reflect an amplification of current public attitude, to wit, that tinkerine with molecules is sort of an ultimate crime against nature. T o counter the popular return to pre-Wohler thinkine. -. we included oreanic lab experiments in which a chemicnl was extracted from natural produrts, such as ipinachor almonds. In the middleof the lab on one occasion, one of the teaching assistants neatly undid my entire effort by barking a t a student, "Take that gum out of your mouth! Chewing gum is almost as bad as chewing organic chemicals!"I am still not sure what she meant by the remark; there are numerous patents on low-molecular-weight copolymers as base stocks for chewing gum. But even venerable DuPout droooed the word chemistrv from their comnanv . . sloean. organic chemists must, I suppose, reel with the punches. A second factor I think has to do with the nature of the students themselves. A generation ago large numbers were from farms or rural areas. Many were used to working hard at chores associated with bad odors and had a sense of a~oreciationfor the effort required to mow a pure crop of &in regardless of the intellekual content of -the process. The job got done even though many important factors, such as the weather, were unforseeable and out of control. Get a group of organic chemists together and you will find them the numerous. essential details of their ~ - - - - -discussine ~ craft, ..."the ehudhoff reaction works best in THF, but doesn't go if there's a nitro group on the molecule. . .no one has been able to duplicate the Selzer synthesis". To mix metaphors, they know the fugue and instantly recognize the sour notes. Scratch a physical chemist and you will find offsnrine of lawvers and the like, who are excited by deterexerted on objects in m i ~ i s t i ~ r e l a t i ohetween & the aclosed room and the temperature of the air. More seriously, I think the growing interrelation of all of the sciences should be an occasion for each subdiscipline to appreciate the contents of the other. The possible benefits of synergism are no better illustrated than with the development of the Woodward-Hoffman rules. Although I now succumb to computer programs to do molecular orbital calculations. I still cannot fathom anvone becoming interested in chemistry by measuring equilib;ium constants and the like. Wibern has suneested in effect that the dullness of contemporary k g h school chemistry texts is due to their excessive content of physical chemistry (2). The one time in the past seven years that I recall the organic lab students showing great interest in an experiment was when they tried to nitrate a sample of cumene that unknowingly contained about 30% cumene hydroperoxide. The reactions overheated and turned all sorts of colors. They were talking about it in the hallways and even in the elevators. The other time the experiments seemed to be appreciated was when they had to develop their own reaction proce~~

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dure, that is, what Pickering spent his summer doing. This invention is a standard experiment in some manuals. The fact that not all the procedures gave the product instilled some degree of respect for the subject. Pickering's drive for intellectual content to simplify the "grammar" of organic chemistry simply doesn't impress me. He realizes in a flash that organic carbonyl chemistry can he explained by nucleophilic attack on carbon followed by loss of water. (Some textbooks present i t this way. Why didn't be look?) Then, I suppose, he heads for the lab to make vinyl bromide by mixing acetaldehyde with aqueous hydrohromic acid, chock full of nucleophilic bromide ions. As with an infant who says he "goed to the store", the successful recognition of general principles does not insure fluency. Literature Clted 1. I8aacs. N. S. Exp~rimentsin Physicai Ormnic 2. Wiborg, K. A c c 1983 16,313.

Chem.Res.

Chmnialry:MacMillan: London, 1969.

G. David Mendenhall Michigan Technological University Houghton, Mi 49931

To the Editor: Professor Mendenhall, you do not have to sell me on the joy of doing organic chemistry. I go a t it with the fervor of a convert. The point of my essay was organic teaching labs are a discredit to thenoble and interesting field of organic chemistry. The average student sees the lab task as "getting through" the preps and unknowns and learns precious little about how organic chemists actually solve problems. Cookbook, cookbook, cookbook.. .how joyless and how unnecessary, considering the real excitement inherent in the field.

Miles Pickerlng Princeton University Princeton. NJ 08544

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A Syllabus for a Two-Semester Chemistry Course for

Health Professions To the Editor: We wish to comment about the paper "A Syllabus for a Two-Semester Chemistry Course for Health Professions" [J.Chem. Educ. 1987 64, 6991. We believe that the main criticism in the proposed program is the lack of a redox section. We consider that the student must know elemental ideas about redox potential, transference of electrons, and oxidized and reduced forms of chemical snecies. because redox reactions are involved in many biological processes. A knowledge of this also seems to he necessary to understand some examples of redox reactions that appear further on in the prorwsed course (sections X11 and XlIlL ~ o r e o i e rwe , disagree with some aspects of section VIII, "Acids, Bases, and Salts". The point l h (2) refers to reactions of arids with metals, whichare not acid-base reartiuns but redox processes. The inrlusion for these electrnn-transfer reactions here will create erroneous concepts for the students. In the same chapter there are two separate blocks, A and B. referine to Arrhenius and Brdnsted theories. respectively. Some topics, such as neutralization processes and titration methods. are listed under Arrhenius theorv, whereas others, such as pH, dissociation constants, and buffers are listed under Rrensted theors. This c c d d lead the student to the erroneous idea that neutralization and titration process-

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Volume 67

Number 6 June 1990

539