leaving groups

PBr3 and SOCl2

PBr3 and SOCl2March 20, 2015

Lately we’ve been talking a lot about converting alcohols to good leaving groups [halides] [tosylates and mesylates] You might think we’d be done already, but not yet! In today’s post we talk about a…

Tosylates And Mesylates

Tosylates And MesylatesMarch 10, 2015

Today we’re going to talk about a different way of making alcohols into good leaving groups – by turning them into tosylates and mesylates (“organosulfonates”). Here’s a brief summary o…

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, …

Guest Post on SN1/SN2/E1/E2 (2): Three And A Half Steps To Any Substitution Or Elimination Reaction

Guest Post on SN1/SN2/E1/E2 (2): Three And A Half Steps To Any Substitution Or Elimination ReactionNovember 7, 2013

The second in a series of guest posts on SN1/SN2/E1/E2 by Chemistry Blog author and “instructor of organic chemistry at a small Midwestern liberal arts college” @azmanam  . For the first post, click here.…

Comparing the E1 and SN1 Reactions

Comparing the E1 and SN1 ReactionsNovember 8, 2012

Imagine you’re starting with the alcohol on the left and you’d like to get to the alkene on the right. What bonds are formed and broken here? We’re forming C-C (π), we’re breaking C-H, and we&…

Walkthrough of Elimination Reactions (1)

Walkthrough of Elimination Reactions (1)August 28, 2012

As you’ve probably noticed by now, organic chemistry is a lot different from physics. Why do I say that? Because when we’re looking to predict what reaction might occur in a given situation, we don’t…

Comparing the SN1 and SN2 Reactions

Comparing the SN1 and SN2 ReactionsAugust 8, 2012

Hey! You can now download a free 1-page Summary Sheet of SN1 vs SN2 reactions containing all the material on this series of blog posts here: Download SN1 vs SN2 Summary Sheet PDF   Since we’ve gone through …

The Conjugate Acid Is A Better Leaving Group

The Conjugate Acid Is A Better Leaving GroupAugust 7, 2012

One of the key factors that determines whether a nucleophilic substitution reaction will happen or not is the identity of the leaving group. Previously, we’ve seen that good leaving groups are weak bases. That m…

The SN1 Mechanism

The SN1 MechanismJuly 13, 2012

Previously we saw that there are two important classes of nucleophilic substitution reactions, which differ in their rate laws, dependence on substitution pattern, and the stereochemistry of the products.  Having gon…

The SN2 Mechanism

The SN2 MechanismJuly 4, 2012

Having gone through the two different types of substitution reactions, and talked about nucleophiles and electrophiles, we’re finally in a position to reveal the mechanism for one of the most important reactions…