What do soap, biodiesel, plastics, and perfumes have in common? Although these substances seem completely different, they are all made from one key component: esters.
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Sign up for freeAs the chain length of esters increases, their solubility _______.
Esters are derived from _______ and __________.
State the strongest type of intermolecular force found between two ester molecules.
As chain length increases, the boiling point of esters ______.
Which molecule has a higher melting point? Their relative masses are given in brackets. Justify your answer.
Which molecule has a higher melting point? Their relative masses are given in brackets. Justify your answer.
State the strongest type of intermolecular force found between two ester molecules.
As chain length increases, the boiling point of esters ______.
Which molecule has a higher melting point? Their relative masses are given in brackets. Justify your answer.
Which molecule has a higher melting point? Their relative masses are given in brackets. Justify your answer.
As the chain length of esters increases, their solubility _______.
Esters are derived from _______ and __________.
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Send FeedbackEsters are organic molecules that are derived from carboxylic acids and alcohols.
Esters are formed from carboxylic acids and alcohols.
You might remember from Carboxylic Acids that carboxylic acids contain a functional group known as the carboxyl group,
Fig. 1 - The general structure of an ester
The general structure of an ester. The R groups can be the same or different. Anna Brewer, Vaia OriginalsTo make esters, we react a carboxylic acid and an alcohol together in the presence of a catalyst. This is known as an esterification reaction. It also produces water.
You’ll learn more about this in Reactions of Esters.
You can easily make esters in the lab by warming a carboxylic acid and an alcohol in a water bath with a few drops of sulfuric acid. When the reaction is complete, pour the mixture into a beaker filled with water. The ester will sit on top of the water whilst the remaining acids and alcohol dissolve in solution. Use your hand to gently waft the air over the beaker towards your nose. It should smell fruity. Esters often smell aromatic, which is why they are used in toiletries, perfumes and household cleaners. In fact, they are even used in common foods as flavourings. Take the ester ethyl ethanoate, for example. It smells like pears, so we use it in hard-boiled sweets.
Fig. 2 - Ethyl ethanoate. This molecule is also known as ethyl acetate
You can see from the molecule above that esters contain one R group with the carbonyl functional group,
Fig. 3 - Making esters
As we found out above, esters are made from two different molecules: a carboxylic acid and an alcohol. Their names come in two parts and reflect these two molecules.
Even if you don’t know which carboxylic acid or alcohol an ester is made from, you can easily work out its name by counting the carbons in its R group chains. Let’s look at a few examples together.
Fig. 4 - Can you name this molecule?
Look at the molecule above. The R group on the left contains the carbonyl group. It must come from a carboxylic acid, so it ends in the suffix -oate. If we count the carbons in its chain, we can see that it has two. Therefore we can give it the root name -eth-. If we put the root name and suffix together, we get ethanoate.
However, that is only half of the story! The R group on the right must come from an alcohol. It has just one carbon in its carbon chain, so we call it methyl. Combining the two names gives us methyl ethanoate.
Fig. 5 - Methyl ethanoate. The methyl part of the name comes from the R group circled in green whilst the ethanoate part comes from the R group circled in red. The carbons are numbered to help you
Remember to include the carbon that is part of the C=O double bond when counting your carbon chain length.
Here is another example.
Fig. 6 - Can you name this molecule?
The R group on the left contains the carbonyl functional group, C=O, and so must come from a carboxylic acid. It has three carbon atoms in its carbon chain, so this part of the ester’s name is propanoate. The R group on the right comes from an alcohol and has four carbons in its chain, giving it the name butyl. We call this molecule butyl propanoate.
Fig. 7 - Butyl propanoate
Notice that when we draw esters, we tend to draw the R group derived from the carboxylic acid on the left and the R group derived from the alcohol on the right. However, when naming them, we name the R group derived from the alcohol first.
The next molecule is very similar to butyl propanoate but it also contains a methyl group and a chlorine atom:
Fig. 8
To find out where exactly on the molecule they are, we need to number the carbons in the carbon chain backbone. We treat each half of the molecule separately.
You’ll remember (see Organic Compounds) that previously we could number the carbons from left to right or right to left - we just wanted all the additional side groups to be on the lowest number carbon possible. This is called the lowest number rule. However, we can’t do that with esters. Instead, we always label the carbons that form the
Fig. 9 - 3-methylbutyl 3-chloropropanoate. The carbon atoms are numbered and R groups circled to help you name the molecule
Instead of saying ethanoate, scientists frequently use the name acetate when talking about esters based on ethanoic acid. For example, methyl ethanoate is commonly called methyl acetate.
Let’s revisit the general structure of an ester.
Fig. 10 - The general structure of an ester
It contains a carbonyl group, the
The single
Fig. 11 - The dipoles within an ester
Esters have higher melting points than similar alkanes but lower melting points than similar alcohols and carboxylic acids. Alkanes are non-polar molecules, and so the only intermolecular forces they experience are weak van der Waal forces. In contrast, esters also have permanent dipole-dipole forces between molecules. These are much stronger than van der Waal forces and require more energy to overcome. However, alcohols and carboxylic acids also contain hydrogen bonds between molecules. These are the strongest type of intermolecular force, and give carboxylic acids and alcohols much higher melting and boiling points than esters.
As with all molecules, longer-chain esters have higher melting and boiling points than shorter-chain esters. This is because larger molecules contain more electrons and so have stronger temporary dipoles, creating stronger van der Waals forces between molecules. Branched esters have lower melting points than straight-chain esters as the branches mean the molecules can’t pack together as tightly. This reduces the attraction between them.
The following table provides some examples of esters, their relative masses and their boiling points.
| Name | Structure | Relative mass | Boiling point (℃) |
| Ethyl ethanoate |
| 88 | 77.1 |
| Propyl ethanoate |
| 116 | 122.5 |
| Butyl butanoate |
| 144 | 166.0 |
| Methylpropyl butanoate |
| 144 | 156.9 |
Here, butyl butanoate has a higher relative molecular mass than both propyl propanoate and ethyl ethanoate because it is a larger molecule. This means that it has a higher boiling point. Methylpropyl butanoate has the same relative mass as butyl butanoate. But because it is branched, the molecules can't pack together as closely. This gives it a lower boiling point.
Although esters cannot form hydrogen bonds with each other, they can form hydrogen bonds with water molecules. This is because they have a lone pair of electrons that can bond with either of the two partially positive hydrogen atoms in water. Because of this, shorter-chain esters are soluble in water. However, longer-chain esters are not. Their non-polar hydrocarbon chains break up the hydrogen bonds, getting in the way of the bonding. This is why we pour a solution after creating an ester into a beaker of water - the ester does not dissolve, and forms a layer instead on the water’s surface.
Fig. 12 - Hydrogen bonding between an ester and a water molecule, shown by the dashed line
For further information on hydrogen bonding and permanent dipole-dipole forces, take a look at Intermolecular Forces.
We’ve already mentioned a few uses of esters: as perfumes, plastics, and flavourings. They can also be found in biodiesel and are often used as plasticisers and solvents. To make soap, we hydrolyse vegetable oils. We’ll explore this further in Reactions of Esters, but for now you just need to know some of the other reactions esters are involved in.
Esters are derived from alcohols and carboxylic acids and have the general formula
When naming esters, we name the R group derived from an alcohol first, followed by the name derived from a carboxylic acid. Esters have the suffix -oate.
Esters contain the polar
Short-chain esters are soluble in water but long-chain esters are not.
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What is an ester?
An ester is an organic molecule derived from a carboxylic acid and an alcohol. It contains the -COO- functional group.
How do you name esters?
You name esters in two stages according to the alcohol and carboxylic acid they are derived from. The first part of the name comes from the alcohol and always ends in -yl. The second part of the name comes from the carboxylic acid and ends in -oate. For example, the carboxylic acid made from methanol and ethanoic acid has the name methyl ethanoate.
What are esters used for?
Esters are commonly used as flavourings in foods like sweets, or in perfumes and cosmetics. They also react in a polymerisation reaction to make polyester plastics. Hydrolysing an ester using a base produces soap. Biodiesel is a type of ester made by reacting vegetable oils with an alcohol such as methanol, and is a renewable fuel source.
How are esters formed?
Esters are formed in a condensation reaction between an alcohol and a carboxylic acid. This needs a strong acid catalyst and is a reversible reaction.
What type of polymers have the ester functional group?
Polyesters are polymers with the ester functional group.
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