hydroboration

Alkyne Addition Reactions – The “Concerted” Pathway

Alkyne Addition Reactions – The “Concerted” Pathway

June 4, 2013

How does the chemistry of alkynes compare to alkenes? As we’ve seen in some previous posts, there are some significant differences, but a lot of the chemistry “rhymes”, if you will. In the series on …

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Hydroboration and Oxymercuration of Alkynes

Hydroboration and Oxymercuration of Alkynes

May 14, 2013

Alkyne chemistry bears many resemblances to alkene chemistry, but in these first few posts on the subject, the purpose is to illustrate how one seemingly minor change – an extra π bond – can lead to sign…

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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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Alkene Addition Pattern #3: The “Concerted” Pathway

Alkene Addition Pattern #3: The “Concerted” Pathway

April 2, 2013

In contrast to alkene addition reactions in the Carbocation Pathway and the 3-Membered Ring Pathway, we saw in the last two posts that hydroboration of alkenes is anomalous. The regioselectivity of the reaction is …

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Hydroboration of Alkenes: The Mechanism

Hydroboration of Alkenes: The Mechanism

March 28, 2013

In the last post we saw that the results of hydroboration of alkenes are not in accord with any of the two families of mechanisms we’ve previously seen (carbocation pathway, 3-membered ring pathway). With hydrob…

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Hydroboration of Alkenes

Hydroboration of Alkenes

March 22, 2013

So far in this series on alkenes, we’ve gone through two families of mechanism pathways. In the carbocation pathway, we saw reactions that proceed with “Markovnikov” regioselectivity, a mixture of &#…

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Reagent Friday: BH3 (Borane)

Reagent Friday: BH3 (Borane)

July 8, 2011

In a blatant plug for the Reagent Guide, each Friday  I profile a different reagent that is commonly encountered in Org 1/ Org 2.  Today’s reagent is a staple of Org 1 and the key representative of a genuinel…

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The Most Annoying Exceptions in Org 1 (Part 1)

The Most Annoying Exceptions in Org 1 (Part 1)

February 1, 2011

One of the common complaints you hear a lot from people learning English is that there are just so many exceptions. The plural of “goose” is “geese”, but the plural of “moose” is &#…

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How Simplicity Breeds Complexity in Organic Chemistry

How Simplicity Breeds Complexity in Organic Chemistry

October 8, 2010

Learning rules is relatively easy. Looking backward from a situation and understanding how those rules led to a specific consequence is a little harder. Predicting the consequences of those rules in the forward direct…

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