Difference Between Ester and Ether

Overview of The Difference Between Ester And Ether

Ester and Ether are two different functional classes of organic compounds. These are the derivatives formed by the process known as esterification/etherification. The key difference between the two lies in their molecular structure. 

What Is Ether?

Ether is a flammable organic compound where oxygen connects the alkyl and aryl groups on either side. They have a general chemical formula R–O–R′. Ether compounds are used in industries, dyes, perfume, oil, and wax.

Structure of Ether:

In the ether, 1 atom of O forms bonds with two C atoms to complete its structure.

For example:


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Ethyl Acetate or Ethyl Ethanoate


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Methyl Butanoate


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propyl Methanoate


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Propyl Ethanoate


Ethyl Propanoate

What Is Etherification?

Etherification or alkylation is a process used for the synthesis of ether by dehydration of alcohol. 

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What is Ester?

Ester is a chemical compound formed by the combination of an organic or inorganic acid. It must have a hydroxyl (–OH) which is swapped by an alkyl (–O–) group. Esters have a pleasant, sweet aroma, hence they are used in synthetic flavouring, perfume, nail polish removers, ink, pharmaceutical industry, and biodiesel.

Structure of Ester:

In the structure of an ester, 2 atoms of O form bonds with 2 C atoms. 

 

For example:

 

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Creatine Ethyl Ester

The general chemical formula for Carboxyl Ester is RCOOR′, where R and R′ are the hydrocarbons. R’ is an alkyl group whereas R may be another alkyl group or hydrogen or an aryl group.

 

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Carboxylic Acid Esters


What is Esterification?

The process of ester formation by the reaction of a carboxylic acid with alcohol is called esterification.

The following key differences between Ester and Ether groups must be considered.

Ester vs Ether: Key Differences On Various Parameters

Verticals

Ether

Ester

Linkage

Ethers are chemical compounds that have single-bonded oxygen in between two simple hydrocarbon chains.

Esters are chemical compounds that have a double bond between oxygen and the adjacent carbon.

Tensile Strength

Ether is flexible

Ester has high tensile & tear strength 

Sliding abrasion

UV & wear-resistant

Greater

Temperature resistance

They are less susceptible to industrial heat

They can withstand high-temperature longer

Boiling Point 

Less than alcohol

Lower than acid and alcohol

Derivative of

alcohol

carboxylic acids

Process of formation

Etherification

Esterification

Functional group

 –O-

–COO

Bonding between oxygen and carbon

Single

Double

Structure

They may have a symmetrical structure

They do not have a symmetrical structure

Polarization

Ethers have both polar or nonpolar bonds

Esters have polar bonds

Water solubility

They are good solvents

They can be soluble in water to some extent

 

Solved Examples

Example 1


Give chemical reactions for butyl acetate. 


Butyl acetate is an ester formed by the esterification reaction of acetic acid and 1-butanol. The reaction takes place in the presence of a mineral catalyst (H+). One molecule of water is liberated in this combination.


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This is a reversible reaction.

Example 2


What Is T-Butyl Methyl Ether? 

tert-butyl methyl ether or Methyl tert-butyl ether (MTBE) is a component of gasoline. It is used as oxygenating to raise the octane number and supplant tetraethyllead. However, it is produced worldwide due to surging demand in Asian markets. The use of MTBE is controversial in the US.

MTBE is also used in medical procedures of the gallbladder to dissolve gallstones.


MTBE is artificially synthesized via the chemical reaction of methanol and isobutylene.

Did You Know? 

In olden times, ether was used as an anaesthetic in surgery. During the Mexican-American War (1846-1848) the doctors began its use as an anaesthetic on the battlefield. Its use is abolished with the development of safer and more effective options available today.

Diethyl ether is the commonest and the first ether used for sedation during the medical procedure. Today, diethyl ether is not easy to buy in most western countries to restrict the massive use by the general public. The drug is used for recreation by people for intoxication.


Still one can find the use of ether in things around. Fluorocarbons produced by ether are used as refrigerants in consumer durables and aerosol propellants. Some medicines related to cough and cold medicines, ointments, toothpaste, and mouthwashes.

Fun Facts:

  • Esters transmit nerve stimuli in animals.

  • The German chemist Leopold Gmelin coined the term ‘Ester’ in the 19th century. The fragrant compounds were called esters then.

  • Ether was discovered in 1275 and its sedative effect was discovered during the Mexican-American War. Later, in 1849 it was officially issued as an anesthetic by the US Army.

FAQ (Frequently Asked Questions)

1. How Do Ethers Name?

Ethers don’t have a distinguishing IUPAC nomenclature suffix. So the substituent name is derived from their alkyl component. For example, Alkyl Group Methyl (CH3–) containing ether is named Methoxy. Similarly, Phenyl (C6H5–) alkyl containing ether is called Phenoxy.


Alternatively, the nomenclature of ether is like naming each of the two carbon groups individually. Like, CH3-CH2-O-CH3 is named ethyl methyl ester. CH3CH2OCH2CH3 is named diethyl ether.

The shorter part is the alkyl group whereas the larger is the alkyl group. Alkyl group is the substituent or alkoxy. The longer side becomes the name of the alkane base. The carbon of each alkyl group on either side is numbered starting from the carbon closest to the oxygen. The shorter side name is appended with the "-oxy" ending.


For example, 


CH3CH2CH2CH2CH2-O-CH2CH2CH3


is named 1-propoxypentane.


2. What compounds are called ester?

An ester is a chemical compound that is a derivation from the chemical reaction of a carboxylic acid and an alcohol. At least one of the –OH (hydroxyl) group is replaced by an –o-alkyl (alkoxy) group. Glycerides, the fatty acid esters of glycerol, are eminent biological esters. It belongs to the group of lipids, and most of the animal fats and vegetable oils contained the same.  Esters of low particle amount are mostly found to make the perfumes of essential oils and pheromones. DNA particles are made up of Phosphoesters. Explosive properties come up through Nitrate esters. Some esters have nice fragrance also, while some are highly soluble. They came under the group of synthetic lubricants in the arena of trade.