A 5-step survival guide to second semester organic chemistry

No matter where you take organic chemistry, what professor you had before or are about to have, how many times you took it before you passed, or what textbook you used (or didn’t bother to buy), the two-semester sequence is a journey of learning quite unlike other college courses. To this day, I remember Dr. Stern and his multi-colored chalk mechanisms, and I have my notes, quizzes, and exams from decades ago.

Now, at the other side of the chalk, I profess this: the second semester organic chemistry course is my absolute favorite to teach. In anticipation of working with 200 possibly-nervous students, I offer this 5-step plan for how to survive second semester organic chemistry.

1. Always build on what you know.

2. Fill in gaps in your knowledge and understanding.

3. Remember what you learned the first semester. It was A LOT. Things like pKa, resonance, formal charge, hybridization, covalent bond descriptions, Newman projections (eclipsed, staggered, gauche, antiperiplanar), cyclohexane conformations and axial vs. equatorial positions, stereochemistry, absolute configuration (R vs S), Cahn-Ingold-Prelog system, mechanisms, nucleophile attacks electrophile, fast and slow steps of kinetics, transition states, rate laws, names of elementary steps (like protonation, deprotonation, nucleophilic attack, leaving group leaves, pi bond formed, carbocation formation, carbocation rearrangement, enol tautomerization), reaction types (like substitution, elimination, addition), specific reaction types and their reagents (like hydration, dehydration, hydrogenation, dehydrogenation, hydrohalogenation, dehydrohalogenation, double dehydrohalogenation, epoxidation, Williamson ether synthesis, Markovnikov and anti-Markovnikov addition), Zaitsev’s Rule, functional groups (like alkyl halide, alcohol, carboxylic acid, aldehyde, ketone, ester, amine, ether, more).

**There’s likely more. That’s just a list off the top of my little head.**

4. Stay calm. Study all the time. Ask questions. Go to lecture. In second semester organic, you’ll need to remember stuff from first semester while you learn oxidation and reduction reactions, conjugation, aromaticity, electrophilic aromatic substitution, formation of tetrahedral intermediate, reactions on carbonyls, Wittig, Grignard, Acetal formation, Fisher esterification, functional group interconversions of carboxylic acid derivatives, Aldol, Claisen, acetoacetic ester synthesis, malonic ester synthesis, many reactions beyond acetylide chemistry for extending the carbon chain, more, more, more mechanisms, heavy emphasis on solving multistep synthesis problems, and designing multistep synthetic schemes.

5. Hold onto your hats. You can do this. It’s gonna be a blast.



One thought on “A 5-step survival guide to second semester organic chemistry

  1. “**There’s likely more. That’s just a list off the top of my little head.**” That’s why I love you! You can write something like that (which is 100% true) when you’re talking about stuff that will make most of your students break down in tears, yet you also write the most delicious prose that can make a reader break down in tears (Or Not to Be is still one of my favorites). I wish I’d had a professor like you when I was in college!

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