What Does “Don’t Memorize!” Mean, Anyway?

September 4, 2015

“Memorize Everything!” was good organic chemistry study advice in 1952. From the MIT Technology Review, a letter to the editor: A Memorable Chemistry Final There is only one final exam that i can date from my four years at MIT. In May of 1952, I took the final for organic chemistry, a course that I […]

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Reproducibility In Organic Chemistry

Reproducibility In Organic Chemistry

September 1, 2015

How One Chemist Playing Hooky From His Day Job Helped To Get A Paper Retracted From Chemistry’s Flagship Journal [In the vein of the recent Chemical & Engineering News perspective on “how the internet has changed chemistry”, [see here for illuminating articles on access to databases, job searching, and education] it seems an opportune moment […]

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Synthesis (6) – Reactions of Alcohols

Synthesis (6) – Reactions of Alcohols

July 27, 2015

The Alcohol Reaction Map Having now finished (at long last) covering the key reactions of alcohols, let’s stop to put everything in perspective. Over the past 18 posts, we covered reactions such as: Ether formation via substitution reactions Elimination of alcohols to form alkenes Conversion of alcohols to alkyl halides via substitution reactions Cleavage of […]

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Thiols And Thioethers

Thiols And Thioethers

July 5, 2015

Here’s a summary of today’s post on thiols: Thiols and Thioethers One of the most powerful insights from learning the periodic table is the fact elements in the same period (column) have similar chemical properties. For instance Alkali metals (Li, Na, K…) all shed an electron relatively easily to form monovalent cations Halogens (F, Cl, Br) […]

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Protecting Groups For Alcohols

Protecting Groups For Alcohols

June 17, 2015

Summary for today’s post on Protecting Groups: When Alcohols Get In the Way As we’ve seen in previous posts in this series, alcohols are very versatile functional groups that participate in a variety of reactions. They can be deprotonated with base (making them good nucleophiles in substitution reactions), protonated (making them good leaving groups in […]

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Intramolecular Reactions of Alcohols and Ethers

Intramolecular Reactions of Alcohols and Ethers

June 12, 2015

“Intramolecular Reactions Make Me Crumple Into The Fetal Position Crying For My Mommy” Here’s a topic which doesnt really fit neatly in with what we’ve discussed before but it’s essential to any discussion of alcohols and ethers. Intramolecular reactions.  Here’s the executive summary: Intramolecular reactions [i.e. reactions where two functional groups in a molecule react […]

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Demystifying Alcohol Oxidations

Demystifying Alcohol Oxidations

May 21, 2015

Today’s post in a nutshell: The Familiar Key Step At The Heart Of (Almost) All Alcohol Oxidation Reactions When I was learning organic chemistry I remember the reagents for oxidation reactions completely coming out of left field. KMnO4, K2Cr2O7, PCC, CrO3, Swern, Dess—Martin ? Hold on. Where did these reagents come from? How do they […]

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Alcohol Oxidation: “Strong” and “Weak” Oxidants

Alcohol Oxidation: “Strong” and “Weak” Oxidants

May 6, 2015

Here’s what we’ll talk about today: reagents for the oxidation of alcohols! Oxidations Of Alcohols With “Eye Of Newt”, “Wing of Bat”, and “Powdered Unicorn Horn” Here we are, at least  fifteen articles into this series on alcohols, and all we’ve really talked about is substitution and elimination reactions, with a little bit of acid-base […]

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Elimination of Alcohols To Alkenes With POCl3

Elimination of Alcohols To Alkenes With POCl3

April 28, 2015

Here’s what we talk about today: more eliminations of alcohols!  Note that this reagent isn’t covered in all courses, but I’ll include it here for completeness’ sake. We’ve talked about 2 ways to convert alcohols to alkenes so far: Option #1: Convert the alcohol to an alkyl halide [with SOCl2, PBr3, or a hydrohalic acid] and then […]

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The SN1, E1, and Alkene Addition Reactions All Pass Through A Carbocation Intermediate

The SN1, E1, and Alkene Addition Reactions All Pass Through A Carbocation Intermediate

April 21, 2015

Was going to include this in my last post but it was getting too big. Note how the SN1, E1, and alkene addition reactions all pass through a carbocation intermediate. Here’s how they’re related. Starting with an alkene, adding strong acid gets us to a carbocation (A–>B). If the counterion to that acid is a […]

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