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The carbonyl group
The carbonyl group (>C=O) is the
functional group found in
compounds such as aldehydes,
ketones, and carboxylic acids.

 In aldehydes the carbonyl group is at

the end of the carbon chain and so has
at least one hydrogen attached to it.

 In ketones the carbonyl group is in the

middle of a carbon chain and so has
two alkyl groups attached to it.

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Representing aldehydes and ketones
Aldehydes and ketones cannot be distinguished by their
molecular formula because they have the same functional
group.

What is the molecular formula of the aldehyde and ketone

below?

an aldehyde a ketone

Both have the molecular formula C3H6O

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Representing aldehydes and ketones
Aldehydes and ketones are therefore represented either
using displayed or structural formulae.

CH3CHO CH3CH2CH2CHO

CH3COCH2CH3 CH3CH2COCH2CH3

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Naming aldehydes
Aldehydes are named using the suffix –al, and follow the
same conventions as for naming alkanes.

ethanal propanal

2-methylbutanal
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Naming ketones
Ketones are named using the suffix –one.

propanone hexan-3-one

Like alkenes, ketones with four or more carbon atoms display

positional isomerism because the carbonyl group may
appear between different carbon atoms. In these cases, a
number is used before the –one to indicate the first carbon
involved.

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Naming aldehydes and ketones activity

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Synthesis of aldehydes and ketones

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Properties of aldehydes and ketones
The carbonyl group is polar due to the
greater electronegativity of oxygen (3.4) than δ+ δ-
carbon (2.6). This influences the properties
of aldehydes and ketones, such as solubility.

Small aldehydes and ketones are soluble

in water due to hydrogen bonding between
a lone pair on the oxygen of the carbonyl
group and the hydrogen of the water.

As size increases, solubility decreases

due to interference in hydrogen
bonding by the hydrocarbon ‘tails’ of
the aldehydes/ketones.

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Boiling points: a comparison

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Boiling points and intermolecular forces
The general increase in boiling points from alkanes to
aldehydes/ketones and alcohols is due to the intermolecular
forces between each type of molecule.

 Alkanes are only held together by van der Waals forces.

These forces increase with the size/length of a molecule.

 The polar carbonyl group in aldehydes and ketones means

that as well as van der Waals forces, these molecules are
also held together by dipole–dipole interactions.

 Alcohols are held together by van der Waals forces and

dipole–dipole interactions. In addition, these molecules can
form hydrogen bonds with each other, due to the slightly
positive hydrogen atom of the hydroxyl group.

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Reactivity of the carbonyl group
Although double bonds require more energy to break than
single bonds, compounds with double bonds tend to be
more reactive as addition reactions are possible.

Some of the chemical properties of δ+ δ-

aldehydes and ketones result from the
polar nature of the C=O bond.

 The positive charge on the carbon atom makes it open

to attack by nucleophiles.

 Aldehydes and ketones can be reduced, forming

primary and secondary alcohols respectively.

 Aldehydes may also be oxidized to carboxylic acids.

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Nucleophilic addition using cyanide

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Dangers of HCN
Hydrogen cyanide (HCN) is highly volatile liquid (boiling point
26 °C), which has a faint bitter almond smell.

In solution, hydrogen cyanide partially dissociates:

HCN(aq) H+(aq) + CN-(aq)

Hydrogen cyanide is highly toxic because it inhibits a

mitochondrial enzyme that is essential for respiration. Being
so volatile and flammable, it is difficult to handle safely.

A safer alternative is potassium cyanide, which is a solid at

room temperature and is therefore easier to handle. An
acidified solution contains both the H+ and CN- ions.

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Reduction of aldehydes and ketones

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Distinguishing aldehydes & ketones

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Detecting a carbonyl group

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Reactions of aldehydes and ketones

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Aldehydes and ketones: true or false?

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Carboxylic acids
Carboxylic acids have a carboxyl group
(-COOH) consisting of a carbonyl group
and a hydroxyl group attached to the
terminal carbonyl carbon.
Carboxylic acids are named using the suffix –oic acid.

Methanoic acid is the simplest carboxylic

acid and is found in bee and ant stings.

Ethanoic acid is the acid that gives vinegar

its sharp taste and smell. It is also important
in the chemical industry and about 6.5
million tonnes are used worldwide each year

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Naming carboxylic acids

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Boiling points of carboxylic acids

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Synthesis of carboxylic acids

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Oxidation of 1° alcohols and aldehydes
Carboxylic acids can be created by the oxidation of aldehydes
by oxidizing agents such as potassium dichromate(VI).

They can also be created by the oxidation of primary alcohols,

again using potassium dichromate(VI).

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Hydrolysis of nitriles
Carboxylic acids can also be prepared by the hydrolysis of
nitriles.

The nitrile is refluxed with water and hydrochloric acid. The

carboxylic acid can then be distilled from the reaction mixture.

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Reactivity of carboxylic acids
The reactivity of carboxylic δ-
acids results, in part, from
δ+
the polarization of its bonds.
δ- δ+

The reactions of carboxylic acids include:

 neutralisation – the carboxylic acid loses a proton to
form a carboxylate salt
 nucleophilic substitution – the positively-charged carbon
is attacked by a nucleophile, resulting in substitution of the
OH group
 esterification – reaction with an alcohol to form an ester.

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Forming the carboxylate ion
Carboxylic acids are weak acids and partially dissociate in
aqueous solution:

carboxylate ion

The negative charge is delocalized across

the carboxylate group, resulting in a more
stable ion. The delocalization is represented
by adding a second dotted line to the carbon
oxygen bonds, which are both equivalent.

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Reactions with carbonates
Carboxylic acids are the only organic compounds that are
strong enough acids to react with either sodium carbonate or
sodium hydrogencarbonate.
Reaction of ethanoic acid and sodium carbonate:

2CH3COOH + Na2CO3 → 2CH3COONa + CO2 + H2O

sodium ethanoate

Reaction of methanoic acid and sodium hydrogencarbonate:

HCOOH + NaHCO3 → HCOONa + CO2 + H2O

sodium methanoate

The formation of bubbles of carbon dioxide gas makes these

reactions useful as a test for carboxylic acids.

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Reactions with alkalis
Carboxylic acids will react with alkalis, such as sodium
hydroxide, in a neutralization reaction:

RCOOH + NaOH → RCOONa + H2O

Reaction of propanoic acid and sodium hydroxide:

CH3CH2COOH + NaOH → CH3CH2COONa + H2O

sodium propanoate

Reaction of butanoic acid and potassium hydroxide:

CH3CH2CH2COOH + KOH → CH3CH2CH2COOK + H2O

potassium butanoate

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Carboxylic acids: a summary

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Glossary

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What’s the keyword?

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Multiple-choice quiz

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