Acyl Chlorides

By Gianna Chibesa
 Table of Contents
01 02
Objectives Acyl Chlorides
Looking at what Looking at this homologous
Cambridge needs us to series and how they are
know formed

03 04
Reactions Summary/Question

Fact file for the reactions Key thinks you need to

of acyl chlorides remember and a chance for
you to practice
2
Syllabus
points

3
 Introduction
Hexanoyl chloride
Benzoyl chloride
• Acyl chlorides are derivatives of carboxylic acids. this means that it contains a carbonyl
functional group but it is not an aldehyde or a ketone.
• The carbonyl functional group C=O.
• We will use the example of ethanoic acid (carboxylic acid) and ethanoyl chloride (acyl
chloride)

Physical Chemical
● They are immiscible in water, but ● They are extremely reactive
eventually react slowly and them ● Take part in substitution
dissolve. reactions
● Contain van der Waals forces of
attraction & dipole-dipole forces 4
 Vital differences
• Compared to haloalkanes, acyl
chlorides have higher boiling
points.
• Carbonyl group is electron-
withdrawing which causes it to
form more dipole-dipole
attractions between the
molecules.
• This increase in intermolecular
forces of attraction is what causes
the boiling point to be higher

5
Production of Acyl Chlorides There are 3 main ways of producing acyl chlorides

Using phosphorous (V) Using sulfur dichloride oxide

chloride

Using phosphorous (III) chloride

R: liquid PCl3
R : solid PCl5 C: heat R: liquid SOCl2
O: steamy fumes of HCl will O: nothing really, the reaction is C: nothing special
form less dramatic than the first E: separate by fractional
E: separate reaction mixture E: separate by fractional distillation
by fractional distillation distillation

6
 Addition-elimination reaction

• Some reactions are addition-elimination reactions

• Undergo these reactions due to their high reactivity
• In these reactions, you must add and then subtract a small molecule
• In the following slides, we will identify such situations
 The 5 reactions

hydrolysis reaction with alcohol

R: water added for hydrolysis, R: a base is needed

C: RTP C: heat
O: steamy fumes of HCl E: this is a faster way of producing an ester
E: this is a vigorous reaction, water compared to the reaction of a carboxylic acid
removed and alcohol.
P: ester is formed
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hydrolysis

9
 The 5 reactions

phenol ammonia

R: NaOH C: heat
C: heat R: ammonia
E: this is the only way to produce phenyl O: white steamy fumes (HCl) if xs ammonia used
esters

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A word about amines
● Amines are compounds which are used
to produce medicines, nylon and rubber

● We need to know the difference

between primary and secondary amines

● PRIMARY → has 1 carbon bonding

● SECONDARY → has 2 carbon atoms
bonded

● The tertiary amine has 3 carbons

bonded to the amine

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 Amines – secondary = substituted

R : acyl chlorides can form amides with

amines through a condensation reaction
R: primary/secondary amine
C: heat

E: the product is a non-substituted amide

when it reacts with ammonia but it is
substituted when it reacts with primary or
secondary amines.

O: white, steamy fumes of Hcl form

Extra info:
https://www.chemguide.co.uk/organicprops/
amines/background.html
12
The need for excess ammonia/amine

13
 Exam
Practice

9701/41/M/J/15
9701/4 O/N/02
Summary
● The acyl chlorides have a
functional group COCl

● They are quite reactive, and we

usually compare them to
haloalkanes

● They take part in addition-

elimination reactions with 5
main functional
groups/substances
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Thank You

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