Master Organic Chemistry

The Hofmann Elimination

October 18, 2017 By James Ashenhurst 3 Comments

The Hofmann Elimination is an elimination reaction of alkylammonium salts that forms C-C double bonds [pi bonds]. [note] It proceeds through a concerted E2 mechanism. In contrast with most elimination reactions that yield alkenes, which follow the Zaitsev (Saytzeff) rule, the Hofmann elimination … [Read more...]

Filed Under: Amines, Organic Chemistry 2 Tagged With: ammonium salt, e2, elimination, gauche, hofmann degradation, hofmann elimination, pkah, steric hindrance

Fused Rings

August 5, 2014 By James Ashenhurst 1 Comment

At the beginning of this series I said that the fact that carbon can form rings leads to all kinds of interesting consequences. We're going to see many examples of that in our post today! So far, we've only talked about cyclic molecules containing one ring. But, of course, molecules with multiple … [Read more...]

Filed Under: Conformations, Organic Chemistry 1, Stereochemistry Tagged With: bicyclic rings, bridgehead, decalin, diastereoselectivity, fused rings, gauche, locked, ring flip, stereoselectivity, trans decalin

Substituted Cyclohexanes: “A Values”

July 1, 2014 By James Ashenhurst Leave a Comment

In the last post we saw that adding a methyl group to cyclohexane results in two chair conformers that are unequal in energy. We saw that the conformer where the methyl group was equatorial is the most stable, since it avoids destabilizing diaxial interactions (technically, gauche interactions) that … [Read more...]

Filed Under: Alkanes, Conformations, Organic Chemistry 1, Uncategorized Tagged With: a value, axial, chair, cycloalkanes, diaxial, equatorial, gauche, t-butyl

Substituted Cyclohexanes – Equatorial vs Axial

June 27, 2014 By James Ashenhurst 2 Comments

Just to bring you up to speed,  let's quickly review the last post.  And at the bottom, I’ll also correct a little fib I made. 1. Cyclohexane Undergoes A Conformational Interconversion Known As A Chair Flip.  In this chair flip, all axial groups become equatorial, and all equatorial groups become … [Read more...]

Filed Under: Conformations, Organic Chemistry 1 Tagged With: a value, axial, cycloalkanes, diaxial, equatorial, equilibrium, gauche, newman, sterics

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