Download Acyl chlorides

Acyl chlorides
The acyl group
Carboxylic acid
RCOOH
Acyl group
RCO
O
O
O
R
Acyl chloride
RCOCl
R
C
R
C
C
Cl
OH
Preparation of an acyl chloride
• From carboxylic acid and thionyl chloride, SOCl2
O
H3C
C
O
+
OH
Ethanoic acid
SOCl2
Thionyl chloride
H3C
C
+
SO2
Cl
Ethanoyl chloride
+
HCl
Acyl chlorides in synthesis
Acyl chlorides react with nucleophiles
O
R
O
C
R
OH
carboxylic acid
C
OR'
H 2O
ester
R'OH
O
R
C
Cl
NH3
acyl chloride
R'NH2
O
R
C
NH2
primary amide
O
R
C
NHR'
secondary amide
Acyl chlorides  Carboxylic acids and Esters
Carboxylic acids using water
O
H 3C
C
O
+
Cl
ethanoyl chloride
H2O
Water
H3 C
+
C
HCl
OH
ethanoic acid
Esters using alcohols
O
O
H3C
C
Cl
ethanoyl chloride
+
CH3CH2CH2
propan-1-ol
Alcohol
OH
H3C
C
+
HHCl
2O
O
CH2CH2CH3
hydrochloric
propyl ethanoate
water
acid
Acyl chlorides  Amides
Primary amides using ammonia
O
O
H3C
C
+
Cl
ethanoyl chloride
2NH3
H3 C
C
+
NH4Cl
NH2
primary amide
Ammonia
Secondary amides using primary amines
O
H3C
C
O
+ 2CH3NH2
Cl
ethanoyl chloride
Primary amine
H3 C
C
N
CH3
H
secondary amide
+ CH3NH3+ Cl