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Chapter 4 Carboxylic Acid Derivatives CHM301
Chapter 4 Carboxylic Acid Derivatives CHM301
Chapter 4 Carboxylic Acid Derivatives CHM301
Carboxylic Acid
Derivatives
Introduction to Carboxylic
Acid Derivatives
a) Acyl halides
b) Acid anhydrides
c) Ester
d) Amides
Acyl Halides
O O
R C OH R C Cl
• The most common are acyl chlorides and
acyl bromides.
O O
R C Cl R C Br
acyl chloride acyl bromide
Example 1:
O
CH3 C Cl
O
CH3CHCH2CH2 C Br
CH3
4-methylpentanoyl bromide
Acid Anhydrides
O O
R C OH + HO C R'
carboxylic acid carboxylic acid
O O
R C O C R' + H2O
acid anhydride
Types of Anhydride
O O
CH 3 C O C CH3
O O
CH3 C O C CH2CH2CH3
O
R C O R'
R C O R'
acid alcohol
O
CH3CH2 C O CH2CH3
ethylpropanoate
Example 2:
CH3 O C
methylbenzoate
Naming Salts of Carboxylic Acids
O
CH3 C O- Na+
Sodium ethanoate
Example 2:
C O- K+
Potassium benzoate
Amides
• Amides are compounds in which a
carbonyl group is connected to a
nitrogen atom.
C NH2
O O
O
CH3CH2CH2 C NH2
butanamide
Example 2:
CH3CH2CONH2
propanamide
Example 3:
C NH2
benzamide
• If there is more than one substituent
bonded to the nitrogen, they are stated
alphabetically.
O CH2CH3
CH3CH2CH2 C N CH2CH3
N,N-diethylbutanamide
Example 2:
O CH3
CH3CH2CH2CH2 C N CH2CH3
N-ethyl-N-methylpentanamide
Classification of Amides
O
CH3CH2CH2 C NH2
butanamide
Secondary Amides
• Nitrogen atom is attached to one
hydrogen atoms.
O CH3
CH3 C NH
N-methylethanamide
Tertiary Amides
O CH3
CH3CH2 C N CH2CH3
N-ethyl-N-methylpropanamide
Nucleophilic Acyl Substitution
O O- O
[1] [2] -
R C Z R C Z R C + Z
-
Nu Nu
Nu
intermediate
Increasing LG ability
-NH
2
-
OH -
OR RCOO- Cl-
Order of Reactivity
Increasing reactivity
O O O O O O
C C C C C C
R NH2 R OH R OR' R O R Cl
R'
least reactive most reactive
Weaker base,
therefore it is a
better leaving group