More organic synthesis books

book review score+5

Organic Synthesis: The Disconnection Approach, 4th ed.
Stuart Warren, Paul Wyatt
Wiley, 2008, 329 pages

This book, now in its fourth edition, explains retrosynthetic organic chemistry, which the authors call “disconnection“—that is, disconnecting the bonds in the product one step at a time and working backward through synthons and ultimately to the starting reagents, which are defined as “something you can buy.” There was nothing really new about this approach, even when this book was first published; it is how most synthetic chemists have always worked, and how organic synthesis is usually taught these days. But Warren and Wyatt's teaching skills are outstanding. The examples are mostly real molecules like (-)-sarracenin, salbutamol, and 6-gingerol—molecules that are fairly simple structurally, but which were actually manufactured and sold. This enhances the reader's confidence that the reaction really works and gives a reasonable yield, which is not something you can assume from all organic chem texts. The writing style is very readable. A background in college-level organic chemistry is assumed. A workbook is available.

One of the biggest challenges in designing syntheses is generating products with the correct stereochemistry. For this, there is only one brief chapter. There is also not very much on protective groups. The goal is not to be complete, but to teach one important skill, and Warren and Wyatt have done an admirable job at that.

Chapter headings relate to corresponding sections in Clayden's Organic Chemistry. The difference between Clayden and classic texts like Morrison and Boyd seems to be that Clayden is more conceptual in its approach, while M&B is organized around different ways to carry out specific reactions, such as “Preparation of ethers”, “Reactions of Alkylbenzenes”, and so forth. Clayden has excellent color diagrams that help undergrads understand the concepts.

Wyatt and Warren continued this approach in the 918-page Organic Synthesis: Strategy and Control, which is billed as an exciting sequel that will keep you “at the coalface of organic synthesis.” I don't know if that's good or bad, but it appears to be a solid advanced organic chem text which I will review later. Strategy and Control is organized around specific types of reactions, but unlike some first-year texts it has references for each reaction.

jul 14, 2013

Organic Synthesis Textbooks

Here are brief reviews of some other organic chemistry textbooks that I have lying around.

Advanced Organic Chemistry, 3rd ed. — Carey and Sundberg
This one is split into two volumes: Structure & Mechanism and Reactions & Synthesis. It's a very well respected book, but the synthesis chapters are organized by reaction type (electrophilic additions, reactions of carbon nucleophiles, etc.) instead of by functional groups, which makes it just a little bit harder to find things. Once you find it, it has references so you can look it up in the literature. But I've found I almost never use it.

Advanced Organic Chemistry: Reactions, Mechanisms, and Structure, 4th ed. — Jerry March
Even the 4th edition of this one, from way back in 1991, had 15,000 references. The 6th edition has 25,000 refs and 2384 pages. Like Carey and Sundberg, it's organized around reaction types instead of functional groups, so it sits on my shelf right next to it, unused most of the time. It's outstanding as a textbook, but in the lab you always have a specific transformation that you need to accomplish. Most people would never think to look in the chapter on free radical substitution to learn how to perform an amidation. In March, that's where it is. But it's well indexed, so it's easy to find.

The Way of Synthesis — Hudlický and Reed
This is more of a monograph on classics in terpene and alkaloid synthesis (which should have been the title) than a real textbook. To chemists, the story about how Woodward first synthesized strychnine back in 1954, or the fact that Yoshikoshi was forced to resort to Vilsmeier reagent to effect a γ-alkylation while struggling with the synthesis of bulnesol, are sexier than Fifty Shades of Grey will ever be.

Organic Chemistry — Morrison and Boyd
The best textbook is the one you're so familiar with that you don't need to use the index. This was the king of undergraduate-level organic back in the day, and even though it's now obsolete it's still a good reference book because of its great organization. M&B organizes reactions around topics like Amines I. Preparation and Physical Properties, Amines II. Reactions, and so forth, which helps if you want to make sure you haven't overlooked a standard reaction. But there are no literature citations, at least in my edition.