Ye Bigge Damne Glossary Of Sugar Nomenclature

Ye Bigge Damne Glossary Of Sugar Nomenclature

February 19, 2018

There’s a lot of sugar nomenclature to know! This post aims to collect the most commonly encountered terms in a typical second-semester organic chemistry course. This reference document from IUPAC was extremely …

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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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The Gabriel Synthesis

The Gabriel Synthesis

January 31, 2018

We’ve seen previously that it’s hard to *usefully* build amines through the SN2 reaction, because once amines start reacting with alkyl halides, the products tend to be more nucleophilic than the reactants…

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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…

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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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Hybridization And Bond Strengths

Hybridization And Bond Strengths

January 19, 2018

Quick quiz. What’s the strongest C–H bond, below? (In other words, which C–H bond has the highest bond-dissociation energy?)  The answer is C. In a), the carbon is sp3 hybridized and the bond dissociation e…

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A Hybridization Shortcut

January 16, 2018

Here’s a shortcut for figuring out the hybridization of an atom in a molecule. This will save you a lot of time. –BEGIN SHORTCUT– Here’s what you do: Look at the atom. Count the number of atoms connect…

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The Haworth Projection

The Haworth Projection

January 11, 2018

Let’s introduce the Haworth Projection, a frequently encountered convention for depicting sugars. “What!?” you may ask.  Yet another drawing convention? At this late stage of the course? And isnR…

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