Where is KMnO4 on the road map?

Lectures on Organic Chemistry. First Edition - Organic Chemistry - Organic Chemistry. First Edition - Organic Chemistry
February 26, 1999

Two heavyweight undergraduate texts from the US and a slimmer volume from the UK present new additions to organic chemistry bookshelves.

In a fully revised, third edition of Organic Chemistry: Structure and Function , Peter Vollhardt and Neil Schore again set out to show that "understanding structure will lead to an understanding of function". Coverage of bonding and stereochemistry comes early, so we are prepared for treatment of the substitution, elimination and addition reactions. Each functional group is then covered systematically with nomenclature and structure before preparations and reactions. "Preparation and reaction road maps" provide comprehensive functional group-at-a-glance summaries. A neat section on "electron-pushing arrows" familiarises the student explicitly with important mechanistic conventions.

Commendably, the importance of synthesis is stressed early on, and a section on retrosynthetic analysis introduces important concepts in multistep transformations. Using tertiary alcohols as an example, analysis and synthesis of molecules using simple organometallic chemistry provides a neat introduction to the topic and draws together material from different chapters.

The authors make a big play about the use of colour to differentiate atomic and hybrid orbitals, and nucleophiles and electrophiles. However, I found the green and blue inks difficult to differentiate in some lights and the overall use of colour a bit too garish. A CD-Rom accompanies the text, which is excellent in comparison to other "with free CD" offers I have seen. Easy-to-use interactive exercises test knowledge of nomenclature and reaction products, and a self-marking extended examination option offers a 70-minute grilling. QuickTime software is used for animated representation of the major classes of reaction mechanism, and the CD-Rom includes .pdb files of molecules referred to in the text. If you have the free plug-in Chemscape Chime these can be easily viewed in their 3D glory using a neat web-browser interface.

Lectures on Organic Chemistry by Cuross Bakhtiar and David Hardy is a much shorter text by design, directed primarily at first-year science undergraduates taking organic chemistry. Its central aim is to provide students with a concise guide to the important, basic reactions of organic chemistry. It is organised with a functional group per chapter, with a basic sub-chapter format of "general", "synthesis" and "reactions". The authors admit that choice of what is "basic" is debatable, and indeed topics such as heterocycles, photochemistry, and carbohydrates would most probably be found in second-year syllabuses.

The production quality of this book is very poor. Diagrams use typefaces of differing sizes, bonds are spidery-thin, mechanism arrows have oversized heads, and rings are distorted. Although these problems may be laid at the door of the publisher, the ultimate sin of the odd pentavalent carbon atom perhaps indicates the lack of overall care with which this book was produced. Errors such as "loosing a proton" will hopefully disappear in subsequent impressions as will, for example, with the definition of SNi mechanism, the occasional discrepancies between different sections of the book.

Rather than being "Lectures on Organic Chemistry" for an undergraduate, the book seemed to me more like "Notes from Organic Chemistry Lectures" by an undergraduate. The authors use phrases such as "doing a reaction", and although such colloquialisms admittedly slip easily off the tongue, they should not really be allowed to creep into teaching texts. Another instance of poor writing is: "KMnO4 is a very vigorous oxidising agent, especially when hot and acidic," again a phrase that would not be unexpected from a student.

The reasoning behind this book has some merit, but the £40 price tag is Everest-steep. Students would be better advised to use their own lecture notes in conjunction with a cheaper mainstream text. The secondary claim that the text could be a "convenient reference and review guide to those who have completed their formal training" is also somewhat misplaced. Students at that stage would want something more than this book provides.

Organic Chemistry by Maitland Jones sets out to illustrate the mechanistic principles behind chemical reactions. The opening chapters deal comprehensively with structure from atoms and atomic orbitals, through molecules and molecular orbitals before dealing with alkanes, alkenes, stereochemistry and rings. The meat of many first-year courses - the SN1, SN2, E1 and E2 reactions - is dealt with together in one long chapter, with electrophilic addition to alkenes following on.

Nestled between these two is a great chapter dealing specifically with matters of enthalpy, entropy, activation energies etc. This topic is handled sensitively from a non-mathematical perspective and will be recommended reading for my first-year students. Advanced chapters include treatment of pericyclic reactions and neighbouring group effects with the standard amino acids and peptides chapter including up-to-date material on synthesis and solid phase methods.

Like Vollhardt and Schore's book, Jones's text offers a multitude of problems. Some are solved in the text, the rest in the accompanying Study Guide/ Solutions Manual . This manual offers excellent detailed explanations to the problems, the level of which is normally only found in the parent book.

No authors dominate this highly competitive area, unlike P. W. Atkins in the world of physical chemistry. Jones is new to the scene, while Vollhardt and Schore do have the advantage of previous editions under their belts. Even though different syllabus structures will always favour one text over another, both these texts are suitable for the trend towards teaching organic chemistry by general mechanistic and structural principles. I recommend that all organic chemists look carefully at these two, though I would give the nod to Jones's book as long as he promises to drop the corny quotes at the start of each chapter.

Andrew Boa is lecturer in organic chemistry, University of Hull.

Lectures on Organic Chemistry. First Edition

Author - Cuross Bakhtiar and David T Hardy
ISBN - 1 86094 053 6
Publisher - World Scientific
Price - £40.00
Pages - 423

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