carboxylic acid derivatives nomenclature and properties
TRANSCRIPT
Carboxylic Acid DerivativesNomenclature and Properties
Dr. Sapna Gupta
Derivatives
• The carboxyl group (-CO2H) is the parent group of a family of compounds called acyl compounds or carboxylic acid derivatives
• The blue component below in the compounds are called “acyl”
Carboxylic Acid Derivatives - Nomenclature and Properties 2
Acyl Chlorides
• Drop the –ic acid and use –yl chloride
Carboxylic Acid Derivatives - Nomenclature and Properties 3
CH3CCl
OO
RC-Cl
O
Cl
O
Cl
O
Benzoyl chlorideEthanoyl chloride(Acetyl chloride)
An acyl group
Hexanedioyl chloride(Adipoyl chloride)
Esters
• Names of esters are based on the carboxylic acid and alcohol.
• Naming is like that of carboxylic acid salts, i.e. alcohol (cation) first and then the acid (anion) and end with –ate.
• Esters are internal groups, so can be found in cyclic compound. These esters are called lactones.
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4-Butanolactone-Butyrolactone)
3-Butanolactone-Butyrolactone)
OO
OO
H3 C
23
12
1
3 4
6-Hexanolactone-Caprolactone)
O
O2
13
45 6
Anhydrides
• Made from dehydrating two carboxylic acids.
• Named by dropping the acid and replacing it with anhydride.
• Anhydrides are internal groups so can be found in cyclic compounds (from diacids).
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Amides
• Amides are made from acid + amine.
• Drop the –oic acid and replace with amide.
• Amides are internal groups, so can be found in a cyclic structure –these are called lactams.
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6-Hexanolactam
-Caprolactam)
H3 C
O
NH
O
NH1
2 1
23
45 6
3
3-Butanolactam
-Butyrolactam)
Nitriles
• Most unusual of all carboxylic acid derivative – there is no oxygen!
• In inorganic chemistry CN- is called cyanide; but in organic its called nitrile.
• To name nitriles, remove –oic acid and replace with nitrile.
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CH3 C N C N CH2 C N
Ethanenitrile(Acetonitrile)
Benzonitrile Phenylethanenitrile(Phenylacetonitrile)
Derivatives and Their Properties
O||
RCClAcyl chloride
O||
RCOREsters
O O|| ||
RCOCRAnhydrides
RCNNitriles
O||
RCNH2
Amides
No H bonding No H bonding No H bonding No H bonding H bonding
Low bpt and mpt
Low bpt and mpt
Low bpt and mpt
Low bpt and mpt
High bpt and mpt
Salts of acidand alcohol
Salts of acid and amines
Solublebecause of reaction
Slightly soluble in water
Solublebecause of reaction
Soluble in water
Pungent odor Fruity smells Pungent odor No odor
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Key Concepts
• Recognize the structure of all derivatives
• Name all types of derivatives
• Predict physical properties of all derivatives
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