Esters

An Exercise In Mind Reading?

April 8, 2013

The other day while going through Claisen condensations with a student, we came upon this pretty typical problem: The student duly deprotonated the alpha carbon of the ester to give the enolate, but stopped there. “Since there’s just one molecule of ester, I’m not sure what it’s supposed to do next.” I explained that it’s [...]

Tagged as: claisen, dieckmann, enolates, esters, medschool

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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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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 [...]

Tagged as: carboxylic acids, ch2n2, diazomethane, esterification, reagent friday, Reagent guide, reagents

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Reagent Friday: Di-isobutyl Aluminum Hydride (DIBAL)

Reagent Friday: Di-isobutyl Aluminum Hydride (DIBAL)

August 26, 2011

In a blatant plug for the Reagent Guide, each Friday  I profile a different reagent that is commonly encountered in Org 1/ Org 2. Version 1.2 just got released, with a host of corrections and a new page index.  DIBAL (Di-isobutyl aluminum hydride) Also known as: DIBAL-H, DIBAH What it’s used for: DIBAL is a strong, [...]

Tagged as: bulky, dibal, hydrides, reagent friday, Reagent guide, reagents app, reducing agents, reduction, steric hindrance

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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 [...]

Tagged as: oxidation, oxidizing agents, reducing agents, reduction, Summary Sheets

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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 [...]

Tagged as: alcohols, aldehydes, alkenes, carboxylic acids, oxidation, reduction

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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 [...]

Tagged as: hydrogenation, oxidation, reduction, weird names

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Reagent Friday: m-CPBA (meta-chloroperoxybenzoic acid)

Reagent Friday: m-CPBA (meta-chloroperoxybenzoic acid)

June 17, 2011

Tagged as: alkenes, baeyer villiger, epoxidation, epoxides, mCPBA, reagent friday, Reagent guide, reagents, reagents app

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The Organic Chemistry Reagent Guide is here!

May 26, 2011

It’s taken a long time – late April through early May was hectic – but today I’m thrilled to finally announce the launch of the “Organic Chemistry Reagent Guide“, a guide designed especially for undergraduate students taking Org1/Org 2. It’s has pretty much all the reagents you need to know about, from Ag2O to Zn(Hg). [...]

Tagged as: acids, bases, oxidants, reagent friday, Reagent guide, reagents, study tips, Summary Sheets

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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 overwhelming, this is true. Today we’ll talk about the simple principle that lies behind the [...]

Tagged as: acid chlorides, acidity, amides, basicity, carboxylic acids, esters, leaving groups, nucleophiles, study tips, summaries

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