Carboxylic acids

Alkene Reactions: Ozonolysis

April 23, 2013

Today’s post represents not so much a pattern in alkene reactions, so much as it does a very common reaction that bears mentioning along with the rest. What makes this reaction special is that it does not simply break the carbon-carbon π bond, as we have been accustomed to seeing, but additionally breaks the C-C σ bond as [...]

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Khan Academy Videos for Organic Chemistry, Part 6

October 30, 2012

In this post (the 6th of 6) we finish up going through all the Khan Academy videos for organic chemistry [videos 65-73]. For previous posts in this series, see [1 2 3 4 5] Video #65 – Keto-Enol Tautomerism Length: 8:03 Summary: 3-methyl 2-butanone is drawn, and the mechanism for its conversion into its enol [...]

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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 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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Reaction Friday – Fischer Esterification

Reaction Friday – Fischer Esterification

April 14, 2012

The Fischer esterification is one of the most important reactions of carboxylic acids. Treatment of carboxylic acids with an alcohol in the presence of acid catalyst leads to the formation of esters, along with the elimination of a molecule of water. It therefore falls into the category of  “condensation reactions”. The reaction is an equilibrium. [...]

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Reagent Friday – Diazomethane (CH2N2)

Reagent Friday – Diazomethane (CH2N2)

November 5, 2011

In a blatant plug for the Reagent Guide and the Reagents App for iPhone, each Friday  I profile a different reagent that is commonly encountered in Org 1/ Org 2.  One of the things about learning organic chemistry from a textbook is that about 98% of you will never really have to consider the practical aspects of working with [...]

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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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Oxidation and Reduction in Organic Chemistry

August 1, 2011

Iron smelting!  Photo credit: http://sclowcountryoutdoors.blogspot.com/2011/02/iron-smelting-at-acba.html In the beginning, the term actually made sense. When the alchemists and medieval metallurgists started doing experiments to quantify exactly how much iron, say was formed from the smelting of a given amount of iron ore, they found that the weight of the solid iron was always less than that of [...]

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