Functional Groups

Summary Sheet: Functional Groups

August 21, 2012

I thought it would be good to make a summary sheet based on functional groups, so here one is: Functional Group Summary Sheet (PDF) You can find other sheets in the Summary Sheets section of this site. In addition, I made some extra summary sheets for Org 1 available on my Shopify Store (15 for [...]

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The Malonic Ester Synthesis

August 14, 2012

Apropos of nothing, here’s a post about a series of reactions that is a common source of student difficulties. It’s called the malonic ester synthesis, and it’s an interesting way of making substituted carboxylic acids. There’s an essentially identical process called the acetoacetic ester synthesis and it makes substituted ketones; the only difference between the two processes is [...]

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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 for its own sake, but for topics that concern the rest of the course. Let’s review [...]

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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 acid base reaction and other types of reactions, which wins? Here’s a good [...]

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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 (key lesson: stronger acid plus stronger base gives weaker acid and weaker base). [...]

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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 – it’s extremely important, in fact – but what do you do when you want to compare the acidity [...]

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Organic Chemistry Study Tips: Reaction Maps

Organic Chemistry Study Tips: Reaction Maps

May 7, 2012

This time of year one of the most common problems students come to me with is how to do synthesis problems. Like this:  There’s a lot of different ways to go about learning how to do synthesis – and I’ll have a lot more to say about that in future posts – but today’s post [...]

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Weird Nomenclature In Carbonyl Chemistry

March 26, 2012

Making it through the chemistry of carbonyl derivatives (ketones, aldehydes, carboxylic acids, esters, and more) there are at least two “weird” nomenclature issues that repeatedly come up to baffle students: Greek letters, and “1,2-” or “1,4-” addition reactions.  In this post I’ll try to address them both.  1. Greek letters The functional group C=O is [...]

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Summary Sheet #8: The Oxidation Ladder

August 15, 2011

Following up on this post, here’s an attempt at trying to put many of the reactions in organic chemistry in perspective, from the standpoint of oxidation state. Note that there’s a lot of gaps – very little on amines, for instance, and no treatment of epoxides or diols – but I hope that people will [...]

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Oxidation Ladders

August 8, 2011

Once you get a handle on oxidations and reductions, you might start to notice that with some molecules these reactions can proceed in sequences. For example, if you start with an alkane with a CH3 group, the alkane can be oxidized to a primary alcohol. The alcohol can be oxidized to an aldehyde The aldehyde [...]

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