ACYL CHLORIDE

LEARNING OUTCOME
At the end of this topic, students should be able to explain:
 Naming of acyl chloride
 Reaction of acyl chlorides with:
1. alcohols and phenols
2. Ammonia and primary amines
INTRODUCTION
 Acyl chlorides are derivatives of carboxylic acids in which the
–OH group has been replaced by a Cl atom
 The acyl group is –COCl
O

Cl

 A typical acyl chloride is ethanoyl chloride

 Structure: Acid Chlorides
 The functional group of an acid halide is an acyl group
bonded to a halogen.
 The most common are the acid chlorides.
 To name, change the suffix -oic acid to -oyl halide.

O O
O O Cl Cl
Cl
RC- CH3 CCl
O
An acyl Ethan oyl ch loride Benzoyl chloride Hexan edioyl ch loride
group (Acetyl ch loride) (Adip oyl chloride)
REACTIONS
 REACTION WITH ALCOHOLS AND
PHENOLS
 Condition: room temperature
 Product: esters
O O

CH3C + H-OCH2CH3 CH3C + HCl

Cl Ethanol OCH2CH3
Ethanoyl chloride Ethyl ethanoate
O O

CH3C
CH3C + H-O + HCl
Cl O

Ethanoyl chloride Phenol

phenyl ethanoate
 O O

C + H-O C
+ HCl
Cl O

Benzoyl chloride Phenol Phenyl benzoate

• the reaction is rapid and does not require heating

• the reaction is useful in making esters

 REACTION WITH AMMONIA
 Condition : room temperature
 Product: amides
Eg
O O

CH3C + NH3 CH3C + HCl

Cl NH2

Ethanoyl chloride Ethanamide

 REACTION WITH PRIMARY AMINES
 Condition: room temperature
 Product: N-substituted amides
Eg
O O

CH3C + CH3CH2NH2 CH3C

+ HCl
Cl NH CH2CH3

Ethanoyl chloride
N-ethyl ethanamide
 TUTORIALS
1. Eugenol is an important compound in many spices, such as
cinnamon. H CO
3

HO CH2CH=CH2

Draw the structure of the organic product formed when

eugenol, dissolved in NaOH(aq), reacts with ethanoyl
chloride.
2. State the reagents and essential conditions necessary to make
phenyl benzoate from an acyl chloride. In each case, write an
equation for the reaction.
3. Using benzoic acids as starting materials, copy and complete
the synthetic pathways shown below.
COOH

PCl5 NH3
? ?
A B

Benzoic acid

C2H5OH
Conc. H2SO4

?
C