Stereochemistry

Optical Purity and Enantiomeric Excess

February 24, 2017

In our last post on optical rotation, we saw that when Louis Pasteur crystallized a salt of a compound then known as “racemic acid” he discovered that it formed two different types of crystals. When redis…

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Optical Rotation, Optical Activity, and Specific Rotation

February 7, 2017

As the title suggests, today’s post is all about optical rotation, optical activity, and specific rotation. This post was co-authored with Matt Pierce of Organic Chemistry Solutions.  Ask Matt about scheduling…

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Assigning R/S To Newman Projections (And Converting Newman To Line Diagrams)

Assigning R/S To Newman Projections (And Converting Newman To Line Diagrams)

February 1, 2017

This post was co-authored with Matt Pierce of Organic Chemistry Solutions.  Ask Matt about scheduling an online tutoring session here. In two recent posts we discussed how to assign (R/S) to configurations of chir…

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Determining R/S (2) – The Method of Dots

Determining R/S (2) – The Method of Dots

January 17, 2017

This post was co-authored with Matt Pierce of Organic Chemistry Solutions.  Ask Matt about scheduling an online tutoring session here. In our first post on the Cahn-Ingold-Prelog (CIP) Rules, we gave a broad overv…

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Introduction to Assigning (R) and (S): The Cahn-Ingold-Prelog Rules

Introduction to Assigning (R) and (S): The Cahn-Ingold-Prelog Rules

October 20, 2016

This post was co-authored by Matt Pierce of Organic Chemistry Solutions.  Ask Matt about scheduling an online tutoring session here. Previously on MOC we’ve described enantiomers: molecules that are non-superim…

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Chiral Allenes And Chiral Axes

Chiral Allenes And Chiral Axes

January 13, 2015

We’ve met alkenes before – right? Just in case you haven’t, let’s review the basics, because today’s post is going to depend on understanding a few of the most important concepts. Alkenes…

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Bridged Bicyclic Rings (And How To Name Them)

Bridged Bicyclic Rings (And How To Name Them)

August 14, 2014

In the last post we started our discussion of structures with more than one ring, using decalin as our key example. We saw how much the stereochemistry at the ring junction can affect the overall shape of the molecul…

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Fused Rings

Fused Rings

August 5, 2014

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 on…

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Cycloalkanes – Dashes And Wedges

Cycloalkanes – Dashes And Wedges

March 20, 2014

In the last post, we mentioned that one of the consequences of the fact that carbon can form rings is that small rings (less than 8 carbons) are so rigid that they can’t be turned inside out [video]. One of the …

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Partial Reduction of Alkynes

Partial Reduction of Alkynes

May 8, 2013

Alkynes bear many similarities to alkenes, but as we have already seen, their chemistry can differ in subtle and interesting ways. Today’s post is another case in point. The reduction of alkenes by hydrogen in …

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