acidity

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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The 2 Most Important Reactions of Alkynes

The 2 Most Important Reactions of Alkynes

May 1, 2013

With the series of posts on alkenes in the can, let’s move on and talk about a closely related functional group that shares many reactions in common with alkenes: acetylenes, or as they are more commonly referre…

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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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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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Walkthrough of Acid Base Reactions (1)

Walkthrough of Acid Base Reactions (1)

April 11, 2012

Now that we’ve described how to figure out where the electrons are in a molecule,  the factors that stabilize negative charge and positive charge, and gone into the curved arrow formalism for reactions, we̵…

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7 Factors that stabilize negative charge in organic chemistry

7 Factors that stabilize negative charge in organic chemistry

February 27, 2012

Like I wrote about last time, it’s good – but not enough – to recognize partial charges and to figure out where they interact. Since reactions involve processes that lead to the gain or loss of charg…

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Common Mistakes with Carbonyls: Carboxylic Acids… Are Acids!

Common Mistakes with Carbonyls: Carboxylic Acids… Are Acids!

May 20, 2011

Carboxylic acids… are acids. I know that seems obvious. But it’s a near certainty that students taking Org 2 for the first time will forget this occasionally. Here are two common mistakes that I see *all the t…

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Simplifying the reactions of carboxylic acid derivatives (part 1)

Simplifying the reactions of carboxylic acid derivatives (part 1)

May 6, 2011

I’ve had a fair number of emails over the past week or two from students who say that they are having a hard time keeping track of all the reactions of carboxylic acids and their derivatives. It can get pretty o…

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