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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Stereochemistry of the Diels-Alder Reaction

Stereochemistry of the Diels-Alder Reaction

November 13, 2017

Here’s what we’ve learned about the Diels Alder reaction so far: [previous post in this series] 3 pi bonds are always broken 2 sigma bonds and a pi bond are always formed, resulting in a new six-membered r…

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Electrophilic Aromatic Substitution – The Mechanism

Electrophilic Aromatic Substitution – The Mechanism

November 9, 2017

Last post in this series on reactions of aromatic groups we introduced activating and deactivating groups in Electrophilic Aromatic Substitution (EAS). We learned that electron-donating substituents on the aromatic ri…

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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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Hybrid Orbitals

Hybrid Orbitals

October 10, 2017

Summary of today’s discussion on hybrid orbitals! [Note: This post was co-authored with Matthew Pierce of Organic Chemistry Solutions.  Ask Matt about scheduling an online tutoring session here. ] In the las…

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Activating and Deactivating Groups In Electrophilic Aromatic Substitution

Activating and Deactivating Groups In Electrophilic Aromatic Substitution

September 26, 2017

Quick summary on what we’ll talk about today, on activating and deactivating groups in electrophilic aromatic substitution: There’s a lot to this post, so here’s a quick index: Electrophilic Aromatic…

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The Hofmann and Curtius Rearrangements

The Hofmann and Curtius Rearrangements

September 19, 2017

Here’s the thing about the coverage of “amines” in Org 2: there’s no narrative. Unlike most chapters, it doesn’t start with a set of concepts and then build up to a series of examples you apply t…

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Reducing Sugars

Reducing Sugars

September 12, 2017

What’s a reducing sugar, and why is it important? Here’s a quick summary. Full details in the post below. Better Living Through Chemistry Q.  Can you think of a situation where it might be useful to be ab…

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Cyclic Dienes and Dienophiles in the Diels-Alder Reaction

Cyclic Dienes and Dienophiles in the Diels-Alder Reaction

September 8, 2017

Last post in this series we introduced the Diels-Alder reaction. We saw that no matter how complex the diene or dienophile, or no matter what substituents are attached, the pattern of bonds that form and break are alw…

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Reductive Amination

Reductive Amination

September 1, 2017

Reminder: Alkylation of Amines Is Rarely The Answer OK – so making amines through direct alkylation is generally not a great way to go. You could even say it’s crappy. What’s the “right” …

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