Aldehydes

Reactions of Grignard Reagents

Reactions of Grignard Reagents

December 10, 2015

Here’s the summary for today’s post: So far in this series we’ve introduced organometallic compounds and said that their carbons tend to be nucleophilic. We’ve learned how to make them from alkyl, alkenyl or aryl halides (along with some ways not to make them!) and saw that they are very strong bases. So what now? […]

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Hydroboration and Oxymercuration of Alkynes

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 […]

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Alkene Reactions: Ozonolysis

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

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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Acid Base Reactions: What’s the Point?

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

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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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

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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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 […]

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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 […]

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