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Liquid Gold: Pheromones In Doe Urine

Liquid Gold: Pheromones In Doe UrineMarch 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 …

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

Our New Book, “Practice Organic Mechanisms”, Is OutMarch 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…

Synthesis (6) – Reactions of Alcohols

Synthesis (6) – Reactions of AlcoholsJuly 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…

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 IntermediateApril 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 w…

Weirdest spam comment I’ve had in awhile

Weirdest spam comment I’ve had in awhileMarch 23, 2015

In the “WTF” category…   Author : Dr abdoul E-mail : cleaninglab@yahoo.com URL : http://www.cleaninglab.ga Comment: WELCOME TO CLEANINGLAB LABORATORIES (PTY) LTD. WE PROVIDE SSD SOLUTION CHEMICA…

How Concepts Build Up In Org 1 (“The Pyramid”)

How Concepts Build Up In Org 1 (“The Pyramid”)September 5, 2014

I LOVE making maps. Whenever I played adventure games as a kid (or, let’s face it, as an adult) I often made meticulous maps of how each area led to the next. Any time I really want to understand something, I have …

Which Cyclohexane Chair Is Of Lower Energy?

Which Cyclohexane Chair Is Of Lower Energy?July 23, 2014

In the last post, we introduced A values and said they were a useful tool for determining which groups are “bulkiest” on a cyclohexane ring. The greater the A-value (bulk), the more favoured the equatorial…

Substituted Cyclohexanes: “A Values”

Substituted Cyclohexanes:  “A Values”July 1, 2014

In the last post we saw that adding a methyl group to cyclohexane results in two chair conformers that are unequal in energy. We saw that the conformer where the methyl group was equatorial is the most stable, sinc…

Cycloalkanes – Ring Strain In Cyclopropane And Cyclobutane

Cycloalkanes – Ring Strain In Cyclopropane And CyclobutaneApril 3, 2014

In the last post we saw that cyclopropane and cyclobutane have an unusually high “ring strain” of 27 kcal/mol and 26 kcal/mol respectively.  We determined this by comparing heats of combustion from rings of vario…

Cycloalkanes – How To Calculate Ring Strain

Cycloalkanes – How To Calculate Ring StrainMarch 24, 2014

In the last post we learned about one consequence of the fact that carbon can form rings – that we can form stereoisomers (cis / trans).  This post attempts to explain another very interesting consequence of ri…