Organic Reactions

The Williamson Ether Synthesis

The Williamson Ether SynthesisOctober 24, 2014

In the last post, we discussed the acid-base properties of alcohols. Two posts ago, we said that acid-base reactions are often used to “set up” substitution and elimination reactions of alcohols.  In this…

Making Music With Mechanisms

Making Music With MechanismsApril 4, 2014

My friend Harry has an annoying habit. When we’re hanging out, every once in awhile, he’ll put on a serious face and say he has something very important to tell me. Then, when he has my attention, he break…

Guest Post On SN1/SN2/E1/E2 (3): Step 1 – The Nucleophile

Guest Post On SN1/SN2/E1/E2 (3): Step 1 – The NucleophileNovember 12, 2013

Following from Adam’s last guest post on the SN1/SN2/E1/E2 (“The Leaving Group“) here is part 3 of the series!  – James Step One: What is the nature of the nucleophile? by @azmanam Last time, …

Initiation, Propagation, Termination

Initiation, Propagation, TerminationSeptember 6, 2013

Waaay back when we started to go through free radical substitution reactions, you might recall that we looked a reaction like this one:   Now that we know a little more about what free radicals are and their key pro…

Alkynes Via Elimination Reactions

Alkynes Via Elimination ReactionsJune 11, 2013

We’ve gone through elimination reactions before – treatment of alkyl halides with base gives alkenes. Some time ago we discussed elimination reactions here. Elimination reactions follow the general pattern…

Organic Reaction Flashcards Version 2.0 Is Here!

Organic Reaction Flashcards Version 2.0 Is Here!May 10, 2013

Do you ever study by making flashcards of reactions? You might recall that a few months ago Rich Apodaca (of Metamolecular) and myself released the first version of The Organic Reactions Flashcard App for iPhone, a mo…

Summary: Alkene Reaction Pathways

Summary: Alkene Reaction PathwaysApril 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…

Alkene Addition Pattern #3: The “Concerted” Pathway

Alkene Addition Pattern #3: The “Concerted” PathwayApril 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 …

Bromination of Alkenes: The Mechanism

Bromination of Alkenes: The MechanismMarch 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 …

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…