bromination

Electrophilic Aromatic Substitution: Introduction

Electrophilic Aromatic Substitution: Introduction

July 11, 2017

Today’s post covers a key reaction of aromatic compounds: electrophilic aromatic substitution. When we covered the reactions of alkenes a while back – a lot of reactions! –  we saw that the vast maj…

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More On 1,2 and 1,4 Additions To Dienes

More On 1,2 and 1,4 Additions To Dienes

April 11, 2017

In the last post we covered 1,2 and 1,4 additions to dienes, specifically the addition of strong acid (e.g. HCl or HBr) to dienes. To recap: In Org 1 we learned that addition of HCl and HBr to normal, isolated alkenes…

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Synthesis (2) – Reactions of Alkanes

Synthesis (2) – Reactions of Alkanes

December 19, 2013

In this post we’re going to begin building our reaction map, starting with the simplest organic compounds of all: alkanes.*We’ve only learned one synthetically important class of alkane reaction: free-radi…

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Bonus Topic: Allylic Rearrangements

Bonus Topic: Allylic Rearrangements

December 2, 2013

In this series on free radical reactions we’ve mostly covered the basics. In this post (and the next one) we’re going to go into a little bit more detail on certain topics that until now I haven’t ha…

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Halogenation At Tiffany’s

Halogenation At Tiffany’s

November 13, 2013

As we discussed in the last post on radicals, bromine radicals are considerably more selective than chlorine radicals in the halogenation of alkanes. For example, a hydrocarbon exposed to Br2 in the presence of heat o…

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Selectivity In Free Radical Reactions

Selectivity In Free Radical Reactions

September 23, 2013

In the last post we showed some examples of how different isomers might be formed in free-radical halogenation of alkanes. And I left off with a question. If we performed a free-radical chlorination on propane with 1 …

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Alkynes Are A Blank Canvas

Alkynes Are A Blank Canvas

June 24, 2013

Now that we’ve gone through all the major reactions of alkynes, we can take a step back and look at the big picture. There are lots of reactions of alkynes. So what? you might ask. In this post I will try to c…

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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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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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Alkene Addition Pattern #2: The “Three-Membered Ring” Pathway

Alkene Addition Pattern #2: The “Three-Membered Ring” Pathway

March 20, 2013

The “Three-Membered Ring” pathway In the last post we walked through a proposal for how the bromination of alkenes works and showed that it adequately explains many of the experimental observations made fo…

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