Three Years

by James

in Teaching

Today is MOC’s third blogaversary.

It’s a common saying in academia that nobody teaches you how to teach. It’s something you learn on the job.  As a Ph.D. organic chemist accustomed to speaking to other Ph.D organic chemists, there were a lot of finer details of learning organic chemistry that I did not appreciate when I set out 3 years ago with a weird idea of independently teaching organic chemistry via Skype and WordPress.

2000 hours of 1-on-1 tutoring later, I have become a connoisseur of organic chemistry mistakes.

These are some of the most common difficulties that students have with organic chemistry that would have surprised me going into this. New instructors of organic chemistry, take note!

James’ Arbitrary Shortlist of Surprising Student Struggles In Learning Organic Chemistry

  • recognizing that Me, CH3 and H3C all refer to the same thing
  • identifying implicit hydrogens and lone pairs in line drawings
  • interpreting condensed formulae such as CH3CH2C(CH3)2C(O)CH3
  • recognizing that CH3CH2CH=CH2 refers to the same thing as the two molecules below:


  • recognizing and applying the reactivity patterns of common functional groups 
  • identifying dipoles through the application of the principle of electronegativity
  • understanding the curved arrow formalism
  • recognizing the reactive portion of a molecule under a given set of conditions and ignoring unimportant details
  • applying reaction patterns to intramolecular cases
  • seeing molecules in perspective (e.g. bridged bicycles in perspective view)
  • identifying the bonds that form and the bonds that break in a reaction. [My obsession. As my students well know, “what bonds form, what bonds break?” will be the most likely expression to be carved on my tombstone].

I am an extraordinarily lucky and grateful man to be able to teach and write about organic chemistry full time. Thank you to all the students, readers, and supporters who have made this possible. #gratitude

In honour of the blog’s third anniversary, lithium:

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{ 4 comments… read them below or add one }


Even us veteran organic chem instructors should take note of the common difficulties. Personally I have tended to assume students know most of that stuff after the first week.



I was surprised too. I’ve met students in org 2 who still struggle with implicit hydrogens. Trying to teach the aldol to someone in that situation is like teaching Shakespeare to a kid who can barely read.



Hip Hip!



Thanks for all the great 3 years of hard work (although I’ve only known this site for much less than that)!


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