Aldehydes

Hydroboration and Oxymercuration of Alkynes

May 14, 2013

Alkyne chemistry bears many resemblances to alkene chemistry, but in these first few posts on the subject, the purpose is to illustrate how one seemingly minor change – an extra π bond – can lead to significant differences in chemical behavior. Previously, we saw that the sp hybridization of alkynes leads to increased acidity, and the [...]

Tagged as: alkenes, alkynes, enol, hydroboration, markovnikov, mercuration, oxymercuration, tautomerism

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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 [...]

Tagged as: carbonyl, carboxylic acid, kmno4, o3, oxidation, oxidative cleavage, ozone, ozonolysis

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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 [...]

Tagged as: khan academy, videos

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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 [...]

Tagged as: acid, base, conjugate acid, conjugate base, electrophiles, nucleophiles

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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 [...]

Tagged as: acidity, basicity, conjugate acid, conjugate base, nucleophile, nucleophilicity, pka, trick questions

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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 [...]

Tagged as: grignard, ketones, reactions, retrosynthesis, secondary alcohols, study tips, synthesis

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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 [...]

Tagged as: 1, 2, 4-addition, aldehydes, alkenes, alpha, dienes, ketones, nomenclature

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Reaction Friday: Formation of Acetals from Ketones

Reaction Friday: Formation of Acetals from Ketones

February 24, 2012

Today’s video is about the formation of acetals from aldehydes and ketones, an important method for the protection of the carbonyl group. One thing I forgot to mention in the video is that the reaction is an equilibrium – choosing alcohol as the solvent ensures that the equilibrium will be driven towards formation of the [...]

Tagged as: acetals, alcohols, aldehydes, ketones, mechanism, Reaction Friday, video

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Reagent Friday: LiAlH[OC(CH3)3]3

Reagent Friday: LiAlH[OC(CH3)3]3

November 11, 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.  Today’s reagent is probably a bit on the obscure side, but it solves a useful problem. Lithium tri tert-butoxy aluminum hydride is lot like lithium aluminum hydride, but with [...]

Tagged as: acid halides, alcohols, bulky, esters, hydrides, LiAlHOtBu3, Reagent guide, reagents app, reducing agents

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Introduction to Oxidative Cleavage Reactions

November 1, 2011

The four posts on acid-base, substitution, addition, and elimination covered the 4 main reactions in organic chemistry I. In this second series of posts we go beyond these to introduce a few of the less common (but still important) reactions you learn in organic chemistry 1. We’ve talked about rearrangements and free-radical substitution: we finish up here with lots of  cleavage (oxidative cleavage). [...]

Tagged as: C-C bond breaking, cleavage, naIO4, o3, oxidation, oxidative cleavage, oxidizing agents, ozone, ozonolysis, pb(oac)4

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