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Dr. Sadia Iqbal

Lecturer
DCOP, DUHS
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At the end of lecture student will be able to

 Define and classify functional groups
 Explain their
 Method of preparation,
 Chemical properties
 Physical properties
 Uses
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Alcohol
Phenols
Carboxylic acids
Anilines
Diazonium salts
Amide
Imide
Amines Lactam
Aldehyde & Ketone
Lactone
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[From Lact ( one ) + am ( ide )] H

O
N
NH

 A lactam is cyclic amide

O

 Any of a group of cyclic amides

characterized by the –NHCO- group, derived from amino-
carboxylic acids by the intra-molecular elimination of water
from the amino and carboxylic groups.
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 Lactam (lactone + amide)
 β-lactam (2 carbon atoms outside the carbonyl, 4
ring atoms in total)
 γ-lactam (3 and 5)
 δ-lactam (4 and 6)
 ε-Lactam (7 ring atoms)
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 To name, add the word lactam to the IUPAC acid

name or replace the -ic acid of common name
with -olactam.

IUPAC name: 3-aminopropanoic acid lactam 6-aminohexanoic acid lactam 4-amino-2-methylpentanoic acid lactam
Common name: β-propiolactam ε-caprolactam α-methyl-ɣ-valerolactam
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 From amide by iodolactamization

 A method for iodocyclization of an amide nitrogen
onto a carbon- carbon double bond.
 As an example, conversion of 5-hexenamide to its
N,O-bis(trimethylsilyl) derivative followed by
treatment with a solution of iodine and aqueous
sodium sulfite quench gave the iodolactam in 64%
overall yield.
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 From amide by iodolactamization

5-hexenamide N,O-bis(trimethylsilyl) derivative iodolactam

Trifluoromethanesulfonate, also known by the trivial name triflate, is a functional

group with the formula CF3SO3−. The triflate group is often represented by −OTf
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 From Ketone (Schmidt Reaction)

Lactams form from cyclic ketone and hydrazoic acid
(HN3)
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 From Amino Carboxylic acid

IUPAC name: 4-aminobutanoic acid 4-aminobutanoic acid lactam

Common name: ɣ-aminobutyric acid ɣ-butyrolactam
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 Reduction (With Lithium alumuinum

hydride)
H3C H3C H
1 LiAlH4, ether
O 2H2O H
H3C H3C
N N

H H
LACTAM
a cylic amine

4-amino-4-methylpentanoic acid lactam

pyrrolidine
ɣ-methyl-ɣ-valerolactam
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 Hydrolysis
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 Amoxicillin

 Cephalexin
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 Carbapenems

 Cephalosporins
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Alcohol
Phenols
Carboxylic acids
Anilines
Diazonium salts
Amide
Imide
Amines Lactone
Aldehyde & Ketone
Lactam
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 Lactone is a cyclic ester which can be seen as

the condensation product of an alcohol group (-OH) and
a carboxylic acid group (-COOH) in the same molecule.
 It is characterized by a closed ring consisting of two or
more C atoms and a single Oxygen atom, with
a ketone group (=O) in one of C adjacent to the Oxygen.
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 Reaction of —OH and —COOH on same

molecule produces a cyclic ester called lactone.
 To name, add the word lactone to the IUPAC acid
name or replace the -ic acid of common name
with -olactone.

IUPAC name: 5-hydroxypentanoic acid lactone 4-hydroxy-2-methylpentanoic acid lactone

Common name: ɣ-valerolactone α-methyl-ɣ-valerolactone
5-pentanolide 2-methyl-4-pentanolide
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 Water-soluble,
 Slightly soluble in ethanol
 Not soluble in ether
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 Hydrolysis
Heating a lactone with a base (sodium hydroxide)
will hydrolyse the lactone to its parent compound, the
straight chained bifunctional compound.
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 Reduction
Lactones can be reduced to diols using lithium
aluminum hydride in dry ether.
The reduction reaction will first break the ester bond
of the lactone, and then reduce the carboxylic acid
group (-COOH) to the alcohol group (-OH).
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 Aminolysis
Lactones also react with ethanolic ammonia, which
will first break the ester bond and then react with the
acidic -COOH group, because of the basic properties
of ammonia, to form a difunctional group, i.e.
alcohol and amide.
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 Regulation of acidity and color in food

 Support of antioxidants and
preservatives
 Lactones contribute significantly to the
flavor of fruit, and of unfermented and
fermented dairy products, and are
therefore used as flavors and
fragrances.
 Polycaprolactone is an important
plastic.
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• Organic chemistry, 4th ed, by Brown Foote Iverson

• Organic chemistry, 5th ed, by John McMarry
• Organic chemistry, 2nd ed, by Paula Yurkanis
Bruice
• Wilson and GISVOLD’S Text book of organic
medicinal and pharmaceutical chemistry, 11th ed,
John, H. Block, John M. Beals, Jr
• Organic chemistry, vol 1, 6th ed, by IL Finar