Beginning Organic Chemistry 2
(paperback, 312 pp; ISBN 0-19-855936-4; $32)
Graham L. Patrick. Oxford University: New York, 1997.

Graham Patrick has written two workbooks whose purpose is to help beginning students master the fundamental concepts, principles, and reactions of organic chemistry through self-study and problem solving. With such mastery the student will develop confidence and skill and have a rewarding experience in the course.

The first workbook, which is the shorter of the two, has 14 sections dealing with such topics as nomenclature, functional groups, isomerism, molecular geometry, and stereochemistry. The second workbook, also of 14 sections, covers the reactions of organic chemistry, including nucleophiles and electrophiles; acids and bases; nucleophilic and eletrophilic substitution and addition; the chemistry of aldehydes, ketones and carboxylic acids; and short discussions of redox and radical reactions. Carbohydrates, amino acids and proteins, polycyclic aromatic hydrocarbons, heterocycles, and the Woodward­Hoffmann rules are not covered in these volumes.

Although problem solving is an integral part of the workbooks, they are much more than compendia of problems. All sections in the two books are organized in the same way. A concept is first presented in detail; this normally includes illustrative examples. The student is then asked to solve a problem related to the concept and to compare the answer with a detailed one given by the author, which follows. Then the next concept is presented in the same fashion, and this continues until the topic has been completely covered. A section may have anywhere from five to 20 of these subsections.

One can judge the success of these or any other books by addressing the questions: Do they fulfill their stated purpose? Are they geared to their audience? Are they error free? As I can answer these questions in the affirmative, I judge them successful. Although the books are written with British spelling and in British vernacular, which mayat least initiallybe off-putting to the typical American student, the writing is clear throughout, with only a rare inelegantly expressed sentence. The writing is casual, almost conversational, and expressed in ways that young people will find appealing. The material is nicely paced; and although presented thoroughly, it is at a level beginning students will understand. The drawings are also nicely done, being large, clear, and error free. I found no more than a dozen or so errors in the nearly 500 pages in the two volumes.

There is one concern a potential user may have: if the order in which the material is presented in the workbooks does not match that in the textbook, will this be a hindrance to learning? I think not. I believe a student can easily jump around in the workbooks to match the material in the textbook without loss of context. The sections are fairly well self-contained.

With any book(s) of such length, one will inevitably find errors and omissions. Although they are not numerous, I wish to mention four. Most notable is the contention that the addition of HCN to aldehydes and ketones is acid catalyzedthat is, the proton is added first to the carbonyl group and the cyanide second. It has been known since the first decade of this century that the reaction occurs by adding cyanide first and the proton second. This error is especially surprising as the mechanism is presented correctly earlier in the section. Second, I also do not like the use of bare protons in reactions, which is done frequently in the workbooks, as these species do not exist in solution. Third, the author in at least one place gets too casual with the concept of resonance, almost implying that a resonance structure is an actual species. Finally, the coverage of enolate chemistry is rather shortwhich is surprising, considering how important this chemistry is to the field. The Claisen condensation, for example, is not discussed. In conclusion, however, I believe the author has fulfilled his purpose. He has written workbooks that will be useful adjuncts to the main textbook. Any beginning student will profit from their use.