Ether: Preparation & Reactions

Instructor: Sarah Pierce

Sarah has a doctorate in chemistry, and 12 years of experience teaching high school chemistry & biology, as well as college level chemistry.

This lesson introduces the organic functional group ethers, and ethers' preparation from an alkoxide ion. Chemical properties such as reactions with chlorine, HI, and oxidation reactions are also discussed.

Pain-Free Surgery

Imagine you are getting ready to have surgery. You put on a hospital gown, lay down on the hospital bed, and watch the nurse begin surgery preparations. The doctor comes in and picks up a scalpel to begin. Isn't there something missing from this scenario? Where is the anesthesia?

While anesthesia was experimented with in surgery, it was not routinely used before the mid-1800s. Before anesthesia, surgeons were not just judged on their ability to conduct surgery, but also on the speed of their surgeries. With no anesthesia, the surgery need to be quick!

In 1842, Crawford W. Long removed a tumor painlessly using diethyl ether, known commonly as just 'ether', as an anesthesia. The use of ether completely changed surgeries. Now, physicians could spend more time on the surgeries themselves, resulting in more precise procedures.

Ether also opened the door to more complex surgeries that weren't able to be conducted before anesthesia, like abdominal surgeries. Let's find out more about this molecule that revolutionized the surgical field.

What is an Ether?

An ether is a molecule that has a oxygen between two hydrocarbon groups. The ether is referred to as a functional group because it is the reactive part of the molecule.

An ether is an oxygen molecule with groups of hydrocarbons on either side. This is diethyl ether, one of the first anesthesia.
diethylether

Williamson Ether Synthesis

Ethers can be made or synthesized using a method discovered by Alexander Williamson, which is aptly named the Williamson ether synthesis. In this process, an alkoxide ion (an alcohol with the hydrogen removed) reacts with an alkyl halide (a halogen attached to a hydrocarbon). This is also called a substitution reaction because the alkoxide ion replaces the halogen.

Ethers can be formed when an alkoxide ion reacts with an alkyl halide
W syn

Ether Reactivity

Compared to other organic molecules, ethers are not very reactive. This is very advantageous to chemists, because this means we can use them as solvents. One of the most common ether solvents used in industry is tetrahydrofuran (THF).

Tetrahydrofuran is a ether that is commonly used as a solvent in organic synthesis reactions
THF

Even though ethers aren't extremely reactive, they can still participate in some reactions. Let's look at a few.

Chlorination

If an ether is part of an aromatic ring, it can react with chlorine to produce 2,4,6-trichloroanisole. This molecule causes wines to have 'cork taint', or a moldy smell.

In this reaction, the presence of the ether directs the chlorine to specific positions on the aromatic ring. Chlorine will only add to the carbon adjacent to the ether, known as the ortho position, or directly across from the ether, known as the para position. Because of this really specific reactivity, the ether group is known as an ortho/para director.

chlorination

Oxidation

Ethers will slowly react with oxygen in the air in an oxidation reaction, forming peroxides. Peroxides are molecules that have a functional group with two oxygens attached to each other.

This is a particularly dangerous reaction because the peroxides are so unstable, they tend to explode! Bomb squads have been summoned to universities to remove old bottles of ether because they have formed peroxides.

Diethyl ether peroxide is the peroxide that is formed when oxygen reacts with diethyl ether
per

To unlock this lesson you must be a Study.com Member.
Create your account

Register to view this lesson

Are you a student or a teacher?

Unlock Your Education

See for yourself why 30 million people use Study.com

Become a Study.com member and start learning now.
Become a Member  Back
What teachers are saying about Study.com
Try it risk-free for 30 days

Earning College Credit

Did you know… We have over 200 college courses that prepare you to earn credit by exam that is accepted by over 1,500 colleges and universities. You can test out of the first two years of college and save thousands off your degree. Anyone can earn credit-by-exam regardless of age or education level.

To learn more, visit our Earning Credit Page

Transferring credit to the school of your choice

Not sure what college you want to attend yet? Study.com has thousands of articles about every imaginable degree, area of study and career path that can help you find the school that's right for you.

Create an account to start this course today
Try it risk-free for 30 days!
Create an account
Support