pka

5 Factors That Affect Basicity of Amines

5 Factors That Affect Basicity of Amines

April 26, 2017

What are the most important factors that affect the basicity of amines? Previously, we’ve seen how to evaluate the basicity of amines by examining the pKa of its conjugate acid (pKaH). (The higher the pKaH, th…

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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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Tosylates And Mesylates

Tosylates And Mesylates

March 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…

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Opening Of Epoxide With Base

Opening Of Epoxide With Base

February 10, 2015

Opening of epoxides with base a summary of what we talk about today: In the last post we discussed the reactions of epoxides under acidic conditions and saw how they resembled the “3-membered ring” family of alken…

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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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Putting Acidity In Perspective

Putting Acidity In Perspective

January 25, 2013

[Source: xkcd  hat tip to Mike Evans @mevans86 for finding this] One concept that always seems to have a hard time getting through is that of pKa. No matter how many times I nag students to “know their pKasR…

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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 (4) – pKa

Walkthrough of Acid-Base reactions (4) – pKa

May 9, 2012

So last time we went through all the different trends that affect acidity. The bottom line is that any factor which stabilizes the conjugate base will result in increased acidity.  Now it’s fine to know trends …

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Walkthrough of Acid-Base Reactions (3) – Acidity Trends

Walkthrough of Acid-Base Reactions (3) – Acidity Trends

April 25, 2012

Let’s review what’s been talked about so far in this series on acid-base reactions: An acid base reaction involves the donation of a proton (H+) from an acid to a base. The species which loses H+ is the ac…

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