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  Home > JCE Print > Journal of Chemical Education > Issues > 1996  > April  >
Features
Reviews
Organic Chemistry
reviewed by John A. Miller
Western Washington University, Bellingham, WA 98225
Cover
April 1996
Vol. 73 No. 4
p. A92

Full Text
Paula Yurkanis Bruice. Prentice-Hall: Englewood Cliffs, NJ, 1995. xxii + 1332 pp. Figs. and tables. 20.9 X 26.2 cm.

To use this textbook one must adhere to the author's philosophy that organic reactions are introduced as the reactions of functional groups using a mechanistic approach. There is no section on the synthesis of a class of compounds in any chapter. The author's overall development of synthetic organic chemistry is one that provides a logical, very well ordered framework that should enhance the students ability to learn the subject. As an example the author's discussion of mechanisms, especially the free radical, SN2, and SN1 using the chemistry of alkyl halides is clear, logical and complete. The discussion of E2 and E1 reactions follows directly after the discussion of the substitution reactions. Unfortunately, there are occasional discussions of some topics that seem internally disjointed. For example the discussion of the electrophilic addition reaction of a hydrogen halide with an alkene rambles. The first example did not allow a precise and orderly presentation of all the essential basic concepts. Likewise the discussion of the E2 reaction initially lacked any reference to the fact that the transition state is trans-coplanar. This aspect was not discussed until after the introduction of the E1 reaction. In contrast inclusion of the significance of the aromatic ring with respects to some reactions is commendable.

There also are occasional discussions that contain minor errors or are not complete, which detract from the general excellent quality of the majority of the discussions. For example, in Chapter 3 the definition of cis and trans in terms of the groups attached to the two carbons in the double bond rather than the longest carbon chain leads to minor inconsistencies in the use of some example compounds. Another example is the presentation of absolute configuration (R, S) of stereoisomers with stereogenic centers. The discussion was easy to understand and the problem associated with the use of a Fischer projection is discussed. Unfortunately, no explanation of how to convert a three-dimensional structure into a Fischer projection or the rules for manipulation of a Fischer projection are included so a student has no method of using the information provided. I was also bothered by the false statement that Emil Fischer assigned R and S to glyceraldehyde when in fact, he was using a completely different system. Likewise, the occasional absence of a topic such as reducing and nonreducing sugars in the chapter on carbohydrates is distracting in terms of a comprehensive coverage. In the case of two spectroscopy chapters the presentation would have been improved if the essential structural aspects being examined were more thoroughly identified on each spectra. The spectroscopy chapters also needed examples with explanations on the determination of a compounds structure using combined IR and NMR data.

Like the majority of textbooks for the one-year course the presentation of reactions is limited almost exclusively to model compounds with only an occasional example being included of how these reactions actually are used in practice. There are, however, individual bioorganic applications and short essays throughout the textbook that add significantly to the interest of the subject presentations. Furthermore, the author's effort to be concise in discussing most subjects has led to a book length that should allow time for considering some of the rather interesting complex synthesis, polymer, and biochemistry topics in chapters 19-28.

More Information
*  Citation
Miller, John A. J. Chem. Educ. 1996 73 A92.
*  Keywords
*  History
Created:
Last Updated:
9/23/1999
5/22/2006
  Home > JCE Print > Journal of Chemical Education > Issues > 1996  > April > Page A92


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