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Organic Chemistry Study Tips

By James Ashenhurst

The Power of Laziness

Last updated: October 6th, 2022 |

What would you do to save 5 seconds?

Let’s say it takes 10 minutes to walk from the gym to class.  Would it matter much to you if it took 10 minutes and 5 seconds instead of 10 minutes?

This is on the way from my campus gym to the local chemistry building.

1-laziness

When they’re alone (or think they are alone) most individuals take the shortcut,  myself included (unless I’m with my wife, who tsk-tsks me for taking the shortcut and is one of the conscientious few who walks the long way even when nobody’s looking).  Groups take the shortcut too – it’s easier in a group, that way there’s more of you if a stranger tsk-tsks you for veering off the path.

I’m nerdy, so I counted this. It’s 19 steps total to walk on the path. It’s 12 steps to take the shortcut. 7 steps is about 5 seconds – taking the shortcut is 5 seconds faster.

Ask those people later, “does it matter to you whether you arrive 5 seconds faster?” and 100% will say no. We say no afterwards because in the abstract, 5 seconds is nothing. But in the present, we care a lot. 5 seconds is a big deal!  Why take the longer route.  What’s the payoff of exerting extra effort?

Five seconds.

Now think about how people would act if they could save 30 seconds, or 10 minutes, or an hour.  Busy people – your professor, your TA, you. Given the choice to omit unnecessary effort with negligible cost, we will do so. We seek the path of least action.

Never underestimate the power of laziness.

You have to learn the shortcuts.

Chemical notation is full of shorthand. If you had to draw out the full structures of molecules every single time, by the end of the course you would go so crazy you would want to douse yourself in honey and lie down on a colony of fire ants.  Your instructors feel the same way. On my drawing program (ChemDraw) I recorded the amount of time it took to draw the “long” version and the “shortcut” version.

Guess which ones your textbooks and instructor are going to use?

2-laziness

Learn abbreviations.

There’s no way around it – you have to learn the meaning of abbreviations such as Ph, Bn, Ts,  Ac, Me, Et, Pr, Bu, t-Bu and so on – in addition to knowing when one can use the  mysterious “R”. After the first few weeks, your instructors aren’t going to bother writing out everything longhand – invest the short amount of time necessary to know what these mean.

Recognizing “hidden” hydrogens and lone pairs is an acquired skill.

In line notation, the C-H bonds and lone pairs might not be drawn, but they’re still there. In the beginning, if it helps to draw out the C-H bonds and lone pairs where necessary do so. But like training wheels, if you practice enough, you’ll eventually grow of having to do this practice. Try to get to this stage as fast as possible, it’s relatively simple and will free your time for material later in the course.

 

00 General Chemistry Review
01 Bonding, Structure, and Resonance
02 Acid Base Reactions
03 Alkanes and Nomenclature
04 Conformations and Cycloalkanes
05 A Primer On Organic Reactions
06 Free Radical Reactions
07 Stereochemistry and Chirality
08 Substitution Reactions
09 Elimination Reactions
10 Rearrangements
11 SN1/SN2/E1/E2 Decision
12 Alkene Reactions
13 Alkyne Reactions
14 Alcohols, Epoxides and Ethers
15 Organometallics
16 Spectroscopy
17 Dienes and MO Theory
18 Aromaticity
19 Reactions of Aromatic Molecules
20 Aldehydes and Ketones
21 Carboxylic Acid Derivatives
22 Enols and Enolates
23 Amines
24 Carbohydrates
25 Fun and Miscellaneous
26 Organic Chemistry Tips and Tricks
27 Case Studies of Successful O-Chem Students

Comments

Comment section

6 thoughts on “The Power of Laziness”

  1. Observation and a question :)

    Wonder how many people have problems understanding the various shortcuts and how that might affect the reputation of ochem as incredibly difficult. Essentially the subject teaches several ways to do the same thing that are just different enough to be confusing for most people if taught at the same time.

    Perhaps a good analogy would be direction giving. When most people are lost and asking directions from another human, they don’t want an answer like “well you could go this way ’bout a mile, then make a right at the broken down tractor. Or you might take this road for half a mile, then take a left onto Old Hillbilly Lane and follow it for ten minutes. Still there’s also…” We tend to want one way to do things at a time.

    As computers overtake paper it might come to pass that the shortcuts won’t be necessary. So my question is could one ignore the shortcuts if they had the time/patience, get comfortable with the material and then come back for the simplified methods later? (Learning just the simple way and coming back for the complete way seems like a bad idea.)

    Reply

    1. I always encourage students to get comfortable with the shorthand as quickly as possible, though I focus on the skeletal structures. The abbreviations (Me, Et, Pr,…) are less critical.
      Using skeletal structures allows you to focus on the important parts of the molecule without getting distracted by every C-H bond in the molecule.
      To use your directions analogy, the short-hand is like saying: “Go straight 5 blocks, then take a right,” while using complete structures would be like saying “Go straight 5 blocks while passing Target, Walmart, KMart, Kroger, Winco, the blue tractor, the gas station, the YMCA, the VFA, the left hander’s store, Walgreens, Culvers, McDonalds, and the minimart, then take a right.”
      The ‘complete instructions,’ are correct, but they include too much distracting information.

      Reply

  2. Ew ew ew. I would NEVER write R-ONa. It is too close to R-O-Na, which would indicate that the oxygen sodium bond is covalent. NaOEt or NaOMe over a reaction arrow, maybe. P

    Reply

  3. Do you happen to know who were the first to use those group abbreviations? They don’t seem to be IUPAC formalised—s-Bu v. sBu and Bus; Et v. Ac (acetyl) v. Ac (actinium); Pr (propyl) v. Pr (praseodymium); Nn (nonyl) v. Nn (naphthalene).

    Reply

  4. I would reccomend drawing the hydrogens at reactive centres, though (say when you’re drawing an SN1 or SN2 mechanism, it can be remarkably easy to lose track of a hydrogen and get the entire answer wrong).

    Having said that, it’d be nice if organic chemistry courses allocated a few lectures to drawing structures.

    A huge number of conventions (the shortcuts you’ve mentioned and others) I’ve seen organic chemistry teachers write up or refer to, without having ever explained them.

    The same deal appears in many textbooks – I don’t think ANY are entirely free from this stuff. I remember reading a sentence in Ege, I think it was, or another one of those textbooks for Org 1, about the importance of learning to draw well – but that was it.

    I actually searched long and hard for a book that would teach when certain mechanistic conventions were allowable, and when they weren’t. A combination of the stuff scattered through Clayden, and Robert Grossman’s excellent book ‘The Art of Writing Reasinable Organic reaction Mechanisms’ have answered most of my questions.

    Reply

    1. It’s true – drawing structures is a crucial skill set which is often very poorly explained.
      Grossman’s first 2 chapters basically cover a lot of the common mistakes that are possible for students in Org 1/ Org 2. Grossman’s rule – which says you should draw out hydrogens at reactive centres, as per your recommendation – should be more widely taught.
      https://masterorganicchemistry.com/2011/10/06/grossmans-rule/

      Reply

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