Reactions of Dienes: 1,2 and 1,4 Addition

March 22, 2017

In today’s post we’ll discuss  1,2- and 1,4- addition to dienes – specifically, the addition of strong acid such as HBr. Here’s the summary of the key points.  Addition To Alkenes, Revisited …

Read the full article →
“Is This Molecule Aromatic?” Some Practice Problems

“Is This Molecule Aromatic?” Some Practice Problems

March 3, 2017

Our last post in this series on aromaticity went through the 4 conditions a molecule must fulfill in order to be aromatic. First, it must be cyclic Second, every atom around the ring must have an available p-orbital T…

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 →
Rules For Aromaticity

Rules For Aromaticity

February 23, 2017

In the last post we introduced the concept of aromaticity, a property of some unusually stable organic molecules such as benzene. Although some aromatic molecules are indeed fragrant (hello, vanillin! ) the term &#…

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 →
Molecular Orbital Diagram For A Simple Pi Bond – Bonding And Antibonding

Molecular Orbital Diagram For A Simple Pi Bond – Bonding And Antibonding

February 14, 2017

In the previous post in this series, “On Conjugation and Resonance“, I warned that in order to gain a deeper understanding of some of the concepts ahead, we’re going to need to go into MO theory. Bu…

Read the full article →

Optical Rotation, Optical Activity, and Specific Rotation

February 7, 2017

As the title suggests, today’s post is all about optical rotation, optical activity, and specific rotation. This post was co-authored with Matt Pierce of Organic Chemistry Solutions.  Ask Matt about scheduling…

Read the full article →
Assigning R/S To Newman Projections (And Converting Newman To Line Diagrams)

Assigning R/S To Newman Projections (And Converting Newman To Line Diagrams)

February 1, 2017

This post was co-authored with Matt Pierce of Organic Chemistry Solutions.  Ask Matt about scheduling an online tutoring session here. In two recent posts we discussed how to assign (R/S) to configurations of chir…

Read the full article →
Conjugation and Resonance

Conjugation and Resonance

January 24, 2017

On Conjugation And Resonance This is the first in a series of posts that will eventually cover conjugation, pi systems, molecular orbital theory, dienes, 1,2- and 1,4- additions, the Diels Alder reaction and other per…

Read the full article →