stereochemistry

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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Alkene Nomenclature: Cis and Trans and E and Z

Alkene Nomenclature: Cis and Trans and E and Z

November 3, 2016

This post was co-authored with Matt Pierce of Organic Chemistry Solutions.  Ask Matt about scheduling an online tutoring session here. Earlier on our MOC series on cycloalkanes, we saw that a key feature of small …

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SOCl2 and the SNi Mechanism

SOCl2 and the SNi Mechanism

February 10, 2014

Some time ago I published this post on Reagent Friday discussing the mechanism of SOCl2 converting secondary alcohols to alkyl chlorides with secondary  through an SN2 pathway: About six months ago this post arrived…

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Summary: Alkene Reaction Pathways

Summary: Alkene Reaction Pathways

April 25, 2013

In this post we’ll do a final review of alkene addition reactions and sum up the three major pathways (and two minor classes of reactions worth paying attention to). Reaction Pathway #1 – The Carbocation P…

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A Fourth Alkene Addition Pattern – Free Radical Addition

A Fourth Alkene Addition Pattern – Free Radical Addition

April 12, 2013

I’ve written that there are three major alkene reactivity patterns [carbocation, three membered ring, and concerted], but there are two minor pathways as well. This post discusses one of them. As discussed previ…

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An Arrow-Pushing Dilemma In Concerted Reactions

An Arrow-Pushing Dilemma In Concerted Reactions

April 5, 2013

Up to now, drawing out reaction mechanisms using the curved arrow formalism has been fairly straightforward. Yes, sometimes there is some ambiguity with respect to which carbon of a C-C π bond is forming a new bond …

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Common Mistakes: Drawing Tetrahedral Carbons

Common Mistakes: Drawing Tetrahedral Carbons

March 12, 2013

There is a knack to drawing proper tetrahedrons. And some very common pitfalls that might not be immediately obvious. One of the challenges that has faced chemists since the days of Van’t Hoff’s controvers…

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Bromination of Alkenes – How Does It Work?

Bromination of Alkenes – How Does It Work?

March 6, 2013

In a previous post we went through the key reactions of the carbocation pathway. It’s a family of reactions which proceed through 1) attack of an alkene upon an acid, forming a free carbocation, and 2) attack of…

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Markovnikov’s Rule (2) – Why It Works

Markovnikov’s Rule (2) – Why It Works

February 11, 2013

Understanding Why Markovnikov’s Rule Works Let’s assemble all the facts we know about the reactions of alkenes with an acid like HCl so far. Regiochemistry: as we saw in the last post, reactions of alkenes…

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Addition Reactions: Stereochemistry

Addition Reactions: Stereochemistry

January 30, 2013

In the last post on alkene addition reactions, we discussed one of the two key themes to look for in addition reactions: regiochemistry (in other words – what “region” of the alkene do different ato…

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