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 …

Tagged as: antarafacial, concerted reactions, diels alder, homo, lumo, molecular orbitals, orbital symmetry, photochemical, suprafacial

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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…

Tagged as: activating, deactivating, directing groups, electrophilic aromatic substitution, meta, ortho, para

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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…

Tagged as: activating, deactivating, electrophilic aromatic substitution, halogens

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Amides: Properties, Synthesis, and Nomenclature

Amides: Properties, Synthesis, and Nomenclature

February 28, 2018

In this post, we’ll try to provide a broad overview of amides.  We’ll provide a brief overview of amide nomenclature, two important properties of amides that differ greatly from amines, and go over three …

Tagged as: acyl, amide nomenclature, amides, dcc, lactam, nitrile, nucleophilic acyl substitution, pyrolysis, socl2

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The Big Damn Post Of Sugar Nomenclature

The Big Damn Post 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 …

Tagged as: aldaric acid, alditol, aldose, alpha and beta, anomer, anomeric carbon, carbohydrates, d and l, disaccharides, epimer, furanose, glycoside, haworth, hexose, ketose, mutarotation, pentose, pyranose, reducing sugars, saccharide, tetrose, triose

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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…

Tagged as: diels alder, dienes, dienophiles, endo, exo

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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…

Tagged as: alkene synthesis, phosphonate, phosphonium, SN2, wittig, ylides

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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…

Tagged as: activating, carbocation stability, deactivating, directing groups, electrophilic aromatic substitution, meta, nitration, ortho, para, reaction energy diagram

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