Review of Atomic Orbitals

Review of Atomic Orbitals

June 7, 2017

[Note: the following article is intended as a quick review on atomic orbitals for students enrolled in an introductory organic chemistry class who are assumed to have taken general chemistry. It is by no means a compl…

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Alkylation of Amines Tends To Be A Pretty Crappy Reaction

Alkylation of Amines Tends To Be A Pretty Crappy Reaction

May 26, 2017

Trends in the basicity of amines provide a classic example of why chemistry is so interesting; it’s deciphering the delicate trade-offs between various general factors in specific cases that gives chemists a buz…

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D and L Sugars

May 24, 2017

What differentiates “D-glucose” from “L-glucose” ? Or D-alanine from L-alanine? What’s this D- and L- nomenclature, anyway? For everyone in a rush, here is the quick and dirty answer: For…

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Frost Circles

Frost Circles

May 17, 2017

We’ve spent a lot of time in previous posts “building up” and drawing out the molecular orbitals for various species. In this post we’ll learn an extremely useful shortcut that will help us dra…

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s-cis and s-trans

s-cis and s-trans

May 12, 2017

s-cis and s-trans. What does those terms mean? Recall cis and trans. The reason Aldrich Chemical Co. can sell 99% cis-2-butene and 99% trans-2-butene in separate bottles is because of restricted rotation about the …

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The Pi Molecular Orbitals of Cyclobutadiene

The Pi Molecular Orbitals of Cyclobutadiene

May 10, 2017

Previously, we’ve seen what the molecular orbitals of benzene look like, and that the fact that they are partially duplexed (or to use the proper nomenclature, “degenerate“) helps to explain benzene…

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The Pi Molecular Orbitals of Benzene

The Pi Molecular Orbitals of Benzene

May 5, 2017

Today, let’s go through how to draw out the molecular orbitals of benzene. We’ll compare them with the molecular orbitals for (linear) hexatriene. The big takeaway is that from contrasting the molecular o…

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The Mesomeric Effect And Aromatic Amines

April 28, 2017

We’ve seen that several key factors influence the basicity of amines – charge, resonance, inductive effects, pi donor / pi acceptor behavior, hybridization and even the contribution of the nitrogen lone pa…

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5 Factors That Affect Basicity of Amines

5 Factors That Affect Basicity of Amines

April 26, 2017

What are the most important factors that affect the basicity of amines? Previously, we’ve seen how to evaluate the basicity of amines by examining the pKa of its conjugate acid (pKaH). (The higher the pKaH, th…

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Basicity of Amines And pKaH

Basicity of Amines And pKaH

April 18, 2017

How do you measure the basicity of an amine? Case in point: what’s a stronger base: pyridine or piperidine? Care to make a prediction? If you said piperidine, congratulations – it is indeed a stronger bas…

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