Organic Chemistry 2

Reactions of Sugars: Glycosylation and Protection

April 24, 2018

If reactions are the meat of an organic chemistry course, then nomenclature is the bun – and you’d be forgiven for thinking that the content in this chapter on sugars has been a little, er, “carb-hea…

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Electrophilic Aromatic Substitutions (1) – Halogenation

Electrophilic Aromatic Substitutions (1) – Halogenation

April 18, 2018

Now that we’ve spent ample time digging into the mechanism of electrophilic aromatic substitution,  activating and deactivating groups, and ortho- ,para– and meta– directors, we’re finally rea…

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Molecular Orbitals in the Diels Alder Reaction

Molecular Orbitals in the Diels Alder Reaction

March 23, 2018

Today we’re going to go into the mechanism of the Diels-Alder reaction from a molecular orbital perspective. Let’s recap where we are with the Diels-Alder so far: The Diels-Alder reaction combines a diene …

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Disubstituted Benzenes: The Strongest Electron-Donor “Wins”

Disubstituted Benzenes: The Strongest Electron-Donor “Wins”

March 19, 2018

Having gone through the mechanism of electrophilic aromatic substitution, explored activating and deactivating substituents, and seen the importance of directing groups, let’s now take the opportunity to use t…

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Why are halogens ortho- para- directors?

March 5, 2018

The previous post in this series tried to show that the key to understanding why a substituent is an ortho-, para- director or meta– director lies in understanding how it influences the stability of the ort…

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Exo vs Endo Products In The Diels Alder: How To Tell Them Apart

February 9, 2018

Today we’ll cover how to tell endo– and exo- products apart in the Diels-Alder reaction. Shortcut below.  For the long winded walkthrough with lots of examples, read the post. Exo and Endo Products in…

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Wittig Reaction

Wittig Reaction

February 6, 2018

Some time ago, we learned how to turn alkenes into carbonyls via ozonolysis. But we haven’t yet learned how to go in the opposite direction – from carbonyls to alkenes. I like to think of functional groups…

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Understanding Ortho, Para, and Meta Directors

Understanding Ortho, Para, and Meta Directors

February 2, 2018

In the previous post we introduced ortho- ,para- and meta- directors in electrophilic aromatic substitution.  Previous to that we covered the mechanism of electrophilic aromatic substitution, and showed that the mec…

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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 …

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The Hofmann Elimination

The Hofmann Elimination

October 18, 2017

The Hofmann Elimination is an elimination reaction that forms C-C double (pi) bonds that specifically occurs when the leaving group is NR3 [note] It proceeds through an E2 mechanism. Although the key concepts are no …

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