Organic Reactions

The Williamson Ether Synthesis

The Williamson Ether Synthesis

October 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…

Read the full article →
Making Music With Mechanisms

Making Music With Mechanisms

April 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…

Read the full article →
Guest Post On SN1/SN2/E1/E2 (3): Step 1 – The Nucleophile

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

November 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, …

Read the full article →
Initiation, Propagation, Termination

Initiation, Propagation, Termination

September 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…

Read the full article →
Alkynes Via Elimination Reactions

Alkynes Via Elimination Reactions

June 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…

Read the full article →
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…

Read the full article →
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…

Read the full article →
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 …

Read the full article →
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 …

Read the full article →
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…

Read the full article →