Uncategorized

The Wolff-Kishner, Clemmensen, And Other Sidechain Reductions

The Wolff-Kishner, Clemmensen, And Other Sidechain Reductions

August 27, 2018

The Great Friedel-Crafts Workaround A recent post covered oxidations on the “benzylic” carbon (i.e. on the carbon adjacent to the aromatic ring). We showed that benzylic C-H bonds are unusually weak, and c…

Read the full article →
Nucleophilicity of Amines

Nucleophilicity of Amines

May 7, 2018

Bonus Topic – Nucleophilicity Of Amines The relative nucleophilicity of amines doesn’t get a  lot of coverage (translation: doesn’t get tested) in many organic chemistry courses, but if we’re going to…

Read the full article →

Ortho-, Para- and Meta- Directors in Electrophilic Aromatic Substitution

January 29, 2018

Two Important Reaction Patterns: Ortho- , Para- and Meta- Directors It’s one thing to learn about electrophilic aromatic substitution reactions of benzene itself. But once you move beyond benzene, that’s w…

Read the full article →
Converting a Fischer Projection To A Haworth (And Vice Versa)

Converting a Fischer Projection To A Haworth (And Vice Versa)

January 25, 2018

Here’s a relatively common problem in the realm of sugar chemistry: “Convert this (sugar) from the Fischer projection to a cyclic pyranose form as a Haworth projection.” (the reverse question can be …

Read the full article →

Pi Molecular Orbitals of Butadiene

February 28, 2017

In the last post in this series we built up the pi molecular orbitals of the allyl pi-system, consisting of three consecutive p orbitals in conjugation. We saw that: The number of molecular orbitals (n) for a pi-syst…

Read the full article →

Optical Purity and Enantiomeric Excess

February 24, 2017

In our last post on optical rotation, we saw that when Louis Pasteur crystallized a salt of a compound then known as “racemic acid” he discovered that it formed two different types of crystals. When redis…

Read the full article →
Molecular Orbitals of The Allyl Cation, Allyl Radical, and Allyl Anion

Molecular Orbitals of The Allyl Cation, Allyl Radical, and Allyl Anion

February 16, 2017

In the last post, we showed how to build a molecular orbital (MO) diagram for a typical C-C pi bond. We saw that: The number of molecular orbitals equalled the number of contributing atomic orbitals. The overlap of …

Read the full article →
Liquid Gold: Pheromones In Doe Urine

Liquid Gold: Pheromones In Doe Urine

March 24, 2016

A few months ago my mom came down to visit, and we had a fun lunch at my favourite aquarium restaurant.  On our drive home, we got on the highway in the rain and turned a corner only to be confronted with a sea of …

Read the full article →
Our New Book, “Practice Organic Mechanisms”, Is Out

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

March 14, 2016

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 Mechanis…

Read the full article →
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 format…

Read the full article →