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The Swern Oxidation: Mechanism and Features

March 31, 2021 By C. Hall 6 Comments

What is the Swern Oxidation? What can you do with this reaction? What is the mechanism of the Swern oxidation? How do you actually run this reaction in the lab and what are their most relevant practical features? These are some of the questions that I will try to answer in this guide, as someone who has run this reaction in the lab countless times.

What Is the Swern Oxidation?

The Swern oxidation is the oxidation of a primary or secondary alcohol to an aldehyde or a ketone, respectively, by the combination of oxalyl chloride and dimethylsulfoxide followed by triethylamine.

the swern oxidation
The Swern Oxidation

Discovery and Applications

The Swern oxidation was first discovered by Daniel Swern and Kanji Omura in 1978. From this point, this methodology evolved into one of the most used strategies to oxidize both secondary and primary alcohols to ketones or aldehydes, respectively.

In this reaction, dimethylsulfoxide (DMSO) acts as the effective oxidizing agent, getting reduced to dimethylsulfide (DMS) as a consequence. However, DMSO by itself is not reactive enough to take part in this redox process, it needs to be activated by oxalyl chloride, (CO)₂Cl₂. This results in the formation of an adduct that can evolve into the corresponding ketone or aldehyde by action of a base (generally triethylamine), upon release of CO, CO₂, and dimethylsulfide (SMe₂), through a beautiful mechanism that is a must know for any student of organic chemistry.

This reaction has distinctive features that make it extremely popular among synthetic chemists.

Advantages and Drawbacks

One of the best features of this oxidation method is that it does not further oxidizes aldehydes to carboxylic acids, so a single 2-electron oxidation of primary alcohols can be achieved. This is often not the case with, for instance, metal-based oxidations, such as the use of potassium permanganate. Other alternatives that stop at the aldehydes, such as DMP, are usually much more expensive than the simple reagents required for the Swern.

… [Read More]

Filed Under: Chemistry Lab, Education and Concepts Tagged With: organic chemistry

A Journey into Substitution Reactions by Crash Course

September 3, 2020 By Guest Posts Leave a Comment

crash course organic chemistry

Note from Chemistry Hall: Today I would like to share with you a recommendation of a YouTube channel. This is how the people at ‘Crash Course’ tackle organic chemistry teaching by using videos. I checked a couple of videos and they explain important concepts in a clear and conversational manner. If you are learning organic… [Read More]

Filed Under: Education and Concepts Tagged With: organic chemistry

What Is the Difference Between Organic and Inorganic Compounds?

March 25, 2020 By C. Hall 1 Comment

organic and inorganic compounds

Wherever we look around, you can see both inorganic and organic compounds. When we go to supermarket, we see different items; some are organic and others are inorganic. What is the difference between organic and inorganic compounds? Well, the chemical difference is not the one you hear on the news which distinguishes “organic” vegetables from… [Read More]

Filed Under: Education and Concepts Tagged With: inorganic chemistry, organic chemistry

Thin Layer Chromatography: A Complete Guide to TLC

January 2, 2020 By C. Hall 31 Comments

tlc guide

If there is one technique or experiment that every chemist, or student learning chemistry should know, it is Thin Layer Chromatography (or TLC for short). If you want to become a synthetic chemist, or you are planning to ace an experimental course on organic chemistry, TLC is something you really need to master. So, what… [Read More]

Filed Under: Chemistry Lab, Featured Tagged With: organic chemistry

How to Use a Molecular Model for Learning Chemistry

December 30, 2019 By C. Hall 1 Comment

molecular model

In this article, we’ll give you some tips on how to use a molecular model for learning chemistry. Nothing can beat a nice molecular model kit for leaning 3D visualization of molecules. In this guide you will learn how to use it, and for what it can be helpful. If you don’t have one yet,… [Read More]

Filed Under: Education and Concepts Tagged With: organic chemistry

SN1 vs SN2 Reactions: What Is Steric Hindrance?

September 21, 2019 By C. Hall 3 Comments

The most important family of reactions that you will study in introductory organic chemistry are substitution reactions. The difference between SN1 vs SN2 types of reactions is a key concept, and it is based upon a key question: what is steric hindrance? If you an organic chemistry student, you definitely need to get a grip… [Read More]

Filed Under: Education and Concepts Tagged With: organic chemistry

What Is the Future of Chemistry? [Artificial Intelligence in Science]

August 30, 2019 By C. Hall 5 Comments

chemistry of the future AI

Everybody has woken up in the morning haunted by the question “how relevant is what I do going to be in the future?”. In case of chemists, all of us wonder what is the future of chemistry sometimes. The answer to this question is especially relevant to the younger generations. Will I be able to… [Read More]

Filed Under: Chemistry Research Highlights Tagged With: organic chemistry, physical chemistry

The Most Important Basic Organic Chemistry Concepts

August 18, 2019 By C. Hall 1 Comment

sterics and electronics

If you are starting to face basic organic chemistry, you may feel overwhelmed with the huge amount of material. Introductory organic chemistry courses can seem like the most difficult ones. But don’t worry! In this post we are going to talk about a “trick” or key concept that will help you along the way. Let’s say,… [Read More]

Filed Under: Education and Concepts Tagged With: organic chemistry

The Best Organic Chemistry Textbook [A Definitive Guide]

June 27, 2019 By C. Hall 28 Comments

Clayden Organic Chemistry Textbook

Let’s face it, organic chemistry can seem difficult to learn. Especially from a beginner’s point of view. For exactly that reason we have put together the definitive guide for choosing the best organic chemistry textbook for your situation. But out of ALL of them, how do you choose the best one? The amount of material… [Read More]

Filed Under: Education and Concepts, Featured Tagged With: organic chemistry

Lab Hacks – How to Increase your Productivity in the Lab

November 19, 2016 By C. Hall 4 Comments

TLC Lab Hacks

I have been working in a chemistry laboratory for some years and still every once in a while I learn new amazing tricks or lab hacks that leave me open-mouthed. Also, it has been a while since I last talked about chemistry lab tricks. For these reason, I decided to share with all of you… [Read More]

Filed Under: Chemistry Lab, Featured Tagged With: inorganic chemistry, organic chemistry

10 Great Lab Tricks To Improve Your Performance

December 22, 2014 By C. Hall 6 Comments

Rainbow Column

I am aware that many of you spend most or a good part of your life working in a laboratory or something related to that, time to share some nice lab tricks. Some people are better than other doing lab research or chemistry experiments, but the basis of why is that true are mainly two:… [Read More]

Filed Under: Chemistry Lab Tagged With: organic chemistry

LSD Synthesis and Discovery: What You May Not Know About It

December 14, 2014 By C. Hall 28 Comments

LSD

Disclaimer: This article is purely informative, and it does not contain information about how to actually carry out experimental procedures for the synthesis of LSD or any drug, which should NOT be attempted at home. Lysergic acid diethylamide, commonly known as LSD, and colloquially called acid is a psychedelic drug which was first synthesized on… [Read More]

Filed Under: Chemistry Research Highlights, Featured Tagged With: organic chemistry

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why do chemicals react

Why Do Chemicals React? Kinetics and Thermodynamics

April 10, 2021 By C. Hall 4 Comments

Chemistry is the science of change. But why do chemical reactions take place? Why do chemicals react with each other? The answer is in thermodynamics and kinetics. These … [Read More...]

How to Learn Chemistry

How To Learn Chemistry at Any Level

January 31, 2020 By C. Hall 2 Comments

Have you ever wanted to learn chemistry, but just didn’t know how to go about doing it? Taking college courses and you don't know how to find resources? There is so much to … [Read More...]

tlc guide

Thin Layer Chromatography: A Complete Guide to TLC

January 2, 2020 By C. Hall 31 Comments

If there is one technique or experiment that every chemist, or student learning chemistry should know, it is Thin Layer Chromatography (or TLC for short). If you want to … [Read More...]

best chemistry set for kids

The Best Chemistry Set for Kids (and Adults!)

January 1, 2020 By Emily McPeek 1 Comment

There’s no better way to learn about chemistry than with fun, hands-on experiments and science projects. Teachers and parents, read on to learn the best chemistry set for kids … [Read More...]

best chemistry textbook

The Best General Chemistry Textbook

August 23, 2019 By C. Hall 1 Comment

The new academic year has already begun in many parts of the world, but it’s never too early to start planning for next year. Time to get your hands into the best general … [Read More...]

best inorganic chemistry textbook

The Best Inorganic Chemistry Textbooks

August 5, 2019 By C. Hall 14 Comments

Inorganic chemistry is one of the cornerstones of the central science. For many is the most fun, but it covers an extremely wide range of topics. For this reason, you need to … [Read More...]

top 100 chemistry facts

100 Fun Chemistry Facts (With Awesome Explanations!)

July 18, 2019 By C. Hall 9 Comments

You probably agree with me on the first fact: chemistry is fascinating. There are plenty of unanswered mysteries within this science, but there are also many interesting and … [Read More...]

Cracking the AP Chemistry Exam

The Best AP Chemistry Review Book

July 5, 2019 By C. Hall 2 Comments

Summer vacation is a time to relax and unwind, but students enrolled in advanced placement (or AP for short) classes for the coming school year are already planning for the … [Read More...]

Clayden Organic Chemistry Textbook

The Best Organic Chemistry Textbook [A Definitive Guide]

June 27, 2019 By C. Hall 28 Comments

Let's face it, organic chemistry can seem difficult to learn. Especially from a beginner's point of view. For exactly that reason we have put together the definitive guide for … [Read More...]

Home Chemistry Lab Experiments

Chemistry Experiments at Home: Setting Up a Home Lab

June 22, 2019 By C. Hall Leave a Comment

Not everybody has access to a professional chemistry lab, so setting up a home chemistry lab is your best bet if you want to do chemistry experiments at home. Chemistry is … [Read More...]

Can we see atoms and molecules?

Can We See Real Atoms and Molecules? Electron Microscopy at a Glance

June 17, 2019 By C. Hall 2 Comments

A universal challenge that has been keeping chemists busy ever since the modern concepts of “atom” and “molecules” were conceived, is how to actually characterize molecular … [Read More...]

TLC Lab Hacks

Lab Hacks – How to Increase your Productivity in the Lab

November 19, 2016 By C. Hall 4 Comments

I have been working in a chemistry laboratory for some years and still every once in a while I learn new amazing tricks or lab hacks that leave me open-mouthed. Also, it has … [Read More...]

LSD

LSD Synthesis and Discovery: What You May Not Know About It

December 14, 2014 By C. Hall 28 Comments

Disclaimer: This article is purely informative, and it does not contain information about how to actually carry out experimental procedures for the synthesis of LSD or any … [Read More...]

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