Carboxylic Acids and Esters

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Carboxylic Acids and Esters
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Carboxylic acids
Carboxylic acids are weak acids with the –COOH

functional group. They are named by adding the
suffix ‘oic acid’. The functional group is always
found at the end of the molecule.
Since carboxylic acids are weak acids, they

partially dissociate into hydrogen ions and
carboxylate ions.
The –COOH group is polar due to the presence

of the electronegative oxygen atoms.
This means that electrons are pulled further

towards the two oxygens, making them slightly
negative. Carbon and hydrogen are therefore
electron-deficient and have a slight positive
charge.
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Like other polar molecules, carboxylic acids can

form hydrogen bonds with water. This enables
the smaller carboxylic acids, such as methanoic
acid and ethanoic acid, to dissolve easily in water.
As the chain length increases (and therefore the

non-polar portion of the molecule increases)
solubility decreases.
Reactions of carboxylic acids
Carboxylic acids react with metal hydroxides

(alkalis) and metal oxides to form a salt and
water.

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They react with metal carbonates to form a salt,

water and carbon dioxide.
Carboxylic acids also react with reactive metals to

form a salt and hydrogen. This is a redox reaction
in which the metal is oxidised and hydrogen is
reduced.

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Acyl chlorides
Acyl chlorides are compounds that contain the –

COCl functional group. They are named using the
suffix –oyl chloride e.g. ethanoyl chloride. The
acyl chloride functional group is always found at
the end of the molecule and the compound is
named with carbon of the acyl group as carbon
number 1.
Acyl chlorides are formed when carboxylic acids

react with thionyl chloride (SOCl2) in which
chlorine displaces the –OH group of the
carboxylic acid.
Reactions of acyl chlorides
Acyl chlorides react with water, alcohols,

ammonia and amines. These reactions happen
readily and easily take place at room temperature
and pressure. They are all nucleophilic addition-
elimination reactions in which chlorine is
substituted by oxygen or nitrogen. White fumes of
hydrogen chloride will be observed.
Acyl chlorides react vigorously with cold water to

form a carboxylic acid and hydrogen chloride.
They also react vigorously with alcohols at room

temperature to form an ester and hydrogen
chloride.

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Acyl chlorides react violently with ammonia at

room temperature to produce a primary amide
and hydrogen chloride.
Acyl chlorides react violently with amines at room

temperature to form a secondary amide and
hydrogen chloride.
Esters are usually made by reacting an alcohol

with a carboxylic acid, but they can also be made
by reacting an acyl chloride with phenol. The
reaction can take place at room temperature and
pressure, but the reaction proceeds slowly. That
said, it’s quicker than reacting phenol with
carboxylic acids, so if you want to make an ester
containing a benzene ring, acyl chlorides are your
best bet.
Esters
If you react an alcohol with a carboxylic acid, you’ll

form an ester. Esters are a homologous series
which contain the functional group ‘-COO’ and
can be identified by their distinctive fruity smell.
They also evaporate easily (we say they are
volatile) which makes them a useful group of
compounds to use in perfumes and food
flavourings.
Let’s look at the reaction between ethanol and

ethanoic acid to produce the ester, ethyl
ethanoate. This reaction requires an acid
catalyst, which is usually concentrated sulfuric
acid.
The removal of water creates the -COO ester

bond, joining the carboxylic acid and alcohol
molecules together to form the ester.
The reaction is reversible so the ester needs to

be separated from the mixture as soon as it is
formed. For smaller esters, this can be done by
warming the mixture and distilling off the ester,
since the ester will be more volatile (evaporates
more easily) than the other components of the
mixture. For larger esters, you’ll need to heat it
under reflux and separate the product by
fractional distillation.
To name esters you use the alcohol as the first

part of the name and the carboxylic acid as the
second part. For example, the ester butyl
propanoate would have been formed by reacting
butanol and propanoic acid together.
Esters can also be made by reacting an alcohol

with an acid anhydride. An acid anhydride is
made by reacting two carboxylic acids together.
The acid anhydride reacts with the alcohol when it

is gently heated. An ester and a carboxylic acid
are formed which are then separated by
fractional distillation. A catalyst is not necessary
for preparing esters in this way.
The third, and final, way to make an ester is by

reacting an acyl chloride with an alcohol. The
products are an ester and fumes of hydrogen
chloride.
Hydrolysis of esters
Esterification is a reversible reaction, which

means that it can also go in the opposite direction
i.e. the ester reacts with water to form a carboxylic
acid and alcohol. Hydrolysis of esters can be
carried out using either an acid or a base.
Acid hydrolysis involves a dilute solution of acid,

such as dilute sulfuric acid or dilute hydrochloric
acid and heating it with the acid under reflux.
Water reacts with the ester to produce the
carboxylic acid and alcohol from which it was
formed.
Alkali hydrolysis involves refluxing the ester with

dilute alkali, such as dilute sodium hydroxide.
This time, you’ll get a carboxylate salt and an
alcohol.
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Carboxylic acids are weak acids with the –COOH

Since carboxylic acids are weak acids, they

The –COOH group is polar due to the presence

This means that electrons are pulled further

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Like other polar molecules, carboxylic acids can

As the chain length increases (and therefore the

Reactions of carboxylic acids

Carboxylic acids react with metal hydroxides

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They react with metal carbonates to form a salt,

Carboxylic acids also react with reactive metals to

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Acyl chlorides are compounds that contain the –

Acyl chlorides are formed when carboxylic acids

Reactions of acyl chlorides

Acyl chlorides react with water, alcohols,

Acyl chlorides react vigorously with cold water to

They also react vigorously with alcohols at room

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Acyl chlorides react violently with ammonia at

Acyl chlorides react violently with amines at room

Esters are usually made by reacting an alcohol

If you react an alcohol with a carboxylic acid, you’ll

Let’s look at the reaction between ethanol and

The removal of water creates the -COO ester

The reaction is reversible so the ester needs to

To name esters you use the alcohol as the first

Esters can also be made by reacting an alcohol

The acid anhydride reacts with the alcohol when it

The third, and final, way to make an ester is by

Esterification is a reversible reaction, which

Acid hydrolysis involves a dilute solution of acid,

Alkali hydrolysis involves refluxing the ester with

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