DAMIETTA
UNIVERSITY
CHEM-103:
BASIC ORGANIC CHEMISTRY
LECTURE 9
Dr Ali El-Agamey
Organic Chemistry, 7th Edition
L. G. Wade, Jr.
Carboxylic Acid Derivatives
2010, Prentice Hall
Acid Derivatives
• All the derivatives can be converted to the
carboxylic acid by acidic or basic hydrolysis.
• Esters and amides are commonly found in
nature.
Chapter 21
Organic Chemistry, 7th Edition
L. G. Wade, Jr.
Esters
© 2010, Prentice Hall
٣
Esters from Carboxylic Acids
• Esters can be made from the reaction of
carboxylic acid and alcohol.
• Excess alcohol is used to drive the equilibrium
toward the ester.
Chapter 21
٥
Nomenclature of Esters
isopropyl methanoate
• Esters are named as alkyl carboxylates.
• The first word is derived from the alkyl group of the
alcohol, and the second word is derived from the
carboxylic acid by changing -ic acid to –ate.
Chapter 21
٦
Homework: Write the IUPAC and common names for each of the
following compound
Homework: Write the IUPAC name for each of the following
compound
Organic Chemistry, 7th Edition
L. G. Wade, Jr.
Amides
© 2010, Prentice Hall
Classes of Amides
3º amide
2º amide
1º amide
• 1 amide has one C—N bond (two N—H).
• 2 amide or N-substituted amide has two C—N bonds
(one N—H).
• 3 amide or N,N-disubstituted amide has three C—N
bonds (no N—H).
Chapter 21
٩
Nomenclature of Amides
IUPAC: N-Ethylethanamide
Common: N-Ethylacetamide
IUPAC: N,N-Dimethylmethanamide
Common: N,N-Dimethylformamide
• For 1 amide, first name the corresponding
acid. Drop -ic acid or -oic acid from the
carboxylic acid name and add -amide.
• For 2 and 3 amides, treat the alkyl groups on
nitrogen as substituents, and specify their
position by the prefix N-.
١٠
Chapter 21
Nomenclature of Amides
IUPAC: N-Ethyl-N,2-dimethylpropanamide
Common: N-Ethyl-N-methylisobutyramide
IUPAC: Cyclopentanecarboxamide
 For cycloalkanes with amide substituent,
the suffix -carboxamide is used.
Chapter 21
١١
Homework: Write the IUPAC name for each of the following
compound
Organic Chemistry, 7th Edition
L. G. Wade, Jr.
Nitriles
© 2010, Prentice Hall
Naming Nitriles
IUPAC: Ethanenitrile
IUPAC: 3-Bromobutanenitrile
Common: Acetonitrile
Common: β-Bromobutyronitrile
• For IUPAC names, add -nitrile to the alkane name.
• Common names come from the carboxylic acid.
Replace -ic acid with -onitrile.
• For cycloalkanes with -CN substituent, the suffix carbonitrile is used.
Chapter 21
١٤
Naming Nitriles
IUPAC: 5-Methoxyhexanenitrile
IUPAC: 3-Cyanopentanoic acid
Common: δ-Methoxycapronitrile
IUPAC: Cyclopropanecarbonitrile
Chapter 21
١٥
Homework: Write the IUPAC name for each of the following
compound
OC2H5
CN
CN
(a)
(c)
(b)
OHC
Cl
CN
O
CN
CN
Br
CN
(e)
(d)
H3CO
HOOC
CN
CN
(g)
(f)
H3C
(h)
Br
CN
(i)
Organic Chemistry, 7th Edition
L. G. Wade, Jr.
Acid Halides
© 2010, Prentice Hall
Acid Halides
O
O
R C Cl
R C Br
acid chloride
(acyl chloride)
acid bromide
(acyl bromide)
• Also called acyl halides.
• These are more reactive than carboxylic acids, so
they are used to synthesize other acid derivatives
such as esters and amides.
Chapter 21
١٨
Acid Halide Nomenclature
O
F
IUPAC: Ethanoyl fluoride
IUPAC: 3-Bromobutanoyl bromide
Common: Acetyl fluoride
Common: β-Bromobutyryl bromide
• For IUPAC and common names acid halides
are named by replacing -ic acid with -yl
halide.
• For cycloalkanes with acid halide substituent,
the suffix –carbonyl halide is used.
١٩
• Acyl chlorides are more common.
Chapter 21
Acid Halide Nomenclature
IUPAC: Propanoyl chloride
IUPAC: Cyclopentanecarbonyl chloride
Common: Propionyl chloride
Homework: Write the IUPAC name for each of the following
compound
Chapter 21
٢٠
Organic Chemistry, 7th Edition
L. G. Wade, Jr.
Acid Anhydrides
© 2010, Prentice Hall
Acid Anhydrides
• Two molecules of acid combine with the loss
of water to form the anhydride.
Chapter 21
٢٢
Anhydride Nomenclature
IUPAC: Ethanoic anhydride
IUPAC: Trifluoroethanoic anhydride
Common: Acetic anhydride
Common: Trifluoroacetic anhydride
• For IUPAC (rarely used) and common names,
the word acid is replaced with anhydride.
• For a mixed anhydride, name both acids.
Chapter 21
٢٣
Anhydride Nomenclature
IUPAC: Ethanoic methanoic anhydride
Common: Acetic formic anhydride
IUPAC: Trifluoroethanoic propanoic anhydride
Common: Trifluoroacetic propionic anhydride
Chapter 21
٢٤