chlorination

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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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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Isomers From Free Radical Reactions

Isomers From Free Radical Reactions

September 17, 2013

Last time we covered a comparatively simple reaction: free-radical chlorination of methane to (CH4) to give chloromethane (CH3Cl) and saw that the reaction proceeds through three stages – initiation (where free …

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Free Radical Reactions

Free Radical Reactions

July 30, 2013

With rare exceptions, until now every reaction we’ve discussed (acid-base, substitution, elimination, addition) has involved the formation of bonds between an electron pair donor (Lewis base) and an electron pai…

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Alkyne Addition Reactions: The 3-Membered Ring Pathway

Alkyne Addition Reactions: The 3-Membered Ring Pathway

May 29, 2013

Last time we discussed the similarities (and differences) between the carbocation pathway for alkenes and alkynes. In this post, we’ll do the same for the “3-membered ring pathway”. If you’ll r…

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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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Bromination of Alkenes: The Mechanism

Bromination of Alkenes: The Mechanism

March 15, 2013

In the last post of this series we showed how the mechanism for bromination of alkenes can’t possibly go through a carbocation intermediate. Why not? We have at least 3 good reasons: The two atoms that form new …

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