conjugate acid

Basicity of Amines And pKaH

Basicity of Amines And pKaH

April 18, 2017

How do you measure the basicity of an amine? Case in point: what’s a stronger base: pyridine or piperidine? Care to make a prediction? If you said piperidine, congratulations – it is indeed a stronger bas…

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Organometallics Are Strong Bases

Organometallics Are Strong Bases

November 13, 2015

Last post we talked about how to make certain organometallics, specifically Grignard and organolithium reagents. One thing we saw is that it’s useful to think of them as “carbanions”, that is, carbon…

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Alcohols (3) – Acidity and Basicity

Alcohols (3) – Acidity and Basicity

October 17, 2014

In the last post we said that one of the keys to the reactions of alcohols as we go forward is that the conjugate acid is a better leaving group and the conjugate base is a better nucleophile. We might have gotten a …

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How To Make Alcohols More Reactive

How To Make Alcohols More Reactive

October 6, 2014

In the last post we explored some of the properties and nomenclature of alcohols. We said that alcohols tend to have high boiling points due to hydrogen bonding, and that  we commonly divide alcohols into the cate…

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Comparing the E1 and SN1 Reactions

Comparing the E1 and SN1 Reactions

November 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&…

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The Conjugate Acid Is A Better Leaving Group

The Conjugate Acid Is A Better Leaving Group

August 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…

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Acid Base Reactions: What’s the Point?

Acid Base Reactions: What’s the Point?

May 30, 2012

One thing has been missing from our discussion of acid-base reactions. Who cares? What does it matter that we understand acid base reactions? Why is it important? Today, I hope to show that it matters a lot, not only …

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Acid Base Reactions Are Fast

Acid Base Reactions Are Fast

May 21, 2012

Common dilemma in organic chemistry as you move through the latter parts of Org 1 and then into Org 2: When more than one reaction is possible, how do you know which one will happen? In a steel cage match between an a…

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A Handy Rule of Thumb for Acid-Base Reactions

A Handy Rule of Thumb for Acid-Base Reactions

May 17, 2012

Last time I talked about pKa and how it’s the closest thing we have to a universal measurement of  the strengths of all kinds of different acids and bases.  I also referred to a post on how to use a pKa table …

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Walkthrough of Acid Base Reactions (2): Basicity

Walkthrough of Acid Base Reactions (2): Basicity

April 16, 2012

Last time I started writing about acid-base reactions. We looked at this list of stabilities of anions going across the topmost row of the periodic table.  Fluoride ion is the most stable in this series because it…

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