Our New Book, “Practice Organic Mechanisms”, Is Out

Today I’m delighted to announce a new book – Practice Organic Mechanisms, co-written with Dr. Michelle Sulikowski, Senior Lecturer of Organic Chemistry at Vanderbilt University.

Practice Organic Mechanisms is a 168-page, spiral-bound, physical book that provides guided mechanism practice for students covering typical first-semester topics:

• substitution and elimination reactions
• reactions of alkenes and alkynes
• reactions of alcohols
• free-radical reactions

The world does not lack for organic chemistry books. So why write yet another one?

Learning reaction mechanisms and curved-arrow pushing is a huge challenge for students in first-semester organic. When students are struggling with mechanisms of organic reactions, where can they go for extra help?

To their textbooks, naturally – and perhaps old exams. However, a general problem with textbooks is that there is typically very few mechanism problems for each reaction, and they are not necessarily very good at reinforcing the common mechanistic steps shared by so many reactions.

How To Use This Book

The point of Practice Organic Mechanisms is that it is a workbook – a book meant to be written and scribbled in – where students can write in the answers to the questions provided, practice the key skills, and gain confidence by doing so.

As Reddit user skier face said on this thread, one of the problems students encounter when learning reactions is that they try to memorize the most basic form of a reaction and then are completely thrown off when there’s a slightly different version: 

Practice Organic Mechanisms addresses this by providing multiple examples of the same reaction, with space provided for students to draw electron-pushing arrows.

For example, in the section on reaction of hydrogen halides with alkenes, here’s how the sequence works:

• An example of the full mechanism on a simple substrate:
• An exercise on a different substrate with all intermediates, where students have to draw in the reaction arrows. 
• Several more exercises on similar substrates of slightly escalating difficulty where students must provide both intermediates and electr0n-pushing arrows (click to see image)

You can see this in action in this 3-page PDF covering that section. (Sample PDF – Addition of Hydrogen Halides To Alkenes)

Besides the six chapters on reactions, there is also an introductory chapter which covers key concepts of organic chemistry, such as drawing line structures, determining formal charge, identifying nucleophiles and leaving groups, how to draw curved arrows, drawing reasonable resonance structures, understanding reactive intermediates, and much more.

Results From Using “Practice Organic Mechanisms” In The Classroom

We have been both surprised and gratified by the positive feedback obtained from using this book in the classroom.

Over 500 students have used this workbook to date, and student response has been exceptionally positive. Furthemore, greater confidence has been observed in students’ abilities to think through mechanism problems and predict product outcomes. More impressively, the score on the mechanism section of the organic examinations has increased from 74% to 82%.

It just goes to show that practice is an effective learning strategy!!

Here’s just one piece of feedback we’ve received (others here):

“This is actually the second time taking organic chemistry 1. While the professor I took the first time around was a great instructor, I always found myself struggling in class, especially on the mechanisms. This book really helped me get to know and practice mechanisms. If there’s one thing I think can be improved, I just wish it were longer! This book actually made orgo not only bearable, but fun.”   – C.A.

Who Can Benefit From “Practice Organic Mechanisms” ?

The book would be a good fit for classes that follow the typical Org 1 curriculum. The textbook that the students used was Klein, 2nd edition, but the material is compatible with all major textbooks.

This book is also appropriate for students who want to practice and develop their electron arrow-pushing skills. If you’re finding this to be a recurring weakness, this book can provide the guided assistance that will help you improve.

Just to be 100% clear, this is not for students looking for specific practice with aromatics,  aldehydes/ketones, carboxylic acid derivatives, and other typical “Org 2” problems.

How To Get A Copy Of “Practice Organic Mechanisms”

Practice Organic Mechanisms is available for sale on Amazon and also on our website, PracticeOrganicMechanisms.co

Instructors who would consider making this book a suggested or recommended book for this class can also contact us for a sample copy. 

Additionally, instructors interested in a bulk purchase (>5 copies) for their class can qualify for a special rate. You might find it more advantageous to deal with us directly than go through your campus bookstore (which generally applies a large markup).

If you use the book, we’d greatly appreciate any feedback, suggestions, and/or reviews!