Lecture Seven

Carboxylic acid salts

Carboxylic acid derivatives are compounds in which the
hydroxyl group is replaced by various other groups. All
acid derivatives can be hydrolyzed to their corresponding
acids
O O

R C OH R C Y

Y = Cl, Br, I We have Acid halides

Y = OR, OR' We have Esters
Y = OCOR We have acid anhydrides
 O O

R C x R C NH2

Acid halides Acid amides

O O O
R C OR R C O C R'

Esters Acid anhydrides

 Esters
The general formula CnH2nO2
O
R C OR' or RCOOR'

Nomenclature:
1) The alkyl group is named first
2) The name of the acid with the –ic ending changed to –ate.
 O
O
H 3C C OCH3
H 3C C OCH2CH3
Com. Methyl acetate Com. Ethyl acetate
IUPAC Methyl ethanoate IUPAC Ethyl ethanoate

O O

H3CH2C C OCH3 H3CH2CH2C C OCH3

Com. Methyl propionate Com. Methyl n-butyrate

IUPAC Methyl propionate IUPAC Methyl butanoate
 O O

H3CH2C C OCH2-CH2-CH3 H3CH2C C OCH CH3

CH3
Com. n-Propyl propionate
Com. iso-Propyl propionate
IUPAC n-propyl propanoate
IUPAC iso-propyl propanoate

O
O
O C CH3
C OCH3

Com. Methyl benzoate Com. Phenyl acetate

IUPAC Methyl benzoate IUPAC Phenyl ethanoate

O
OCH2 CH3
O
C
H3C HC C OCH CH3
C
H3C CH3
O OCH2 CH3

Com. iso-propyl isobutyrate Com. Diethyl oxalate

IUPAC iso-Propyl-2-methylpropanoate IUPAC Diethyl ethandioate
 Amides
Nomenclature:
A) Common name:
Dropping the suffix –ic from the name of the parent acid and adding
the suffix amide

B) IUPAC name:
Acid amide are named as alkane amide

C) For Common and IUPAC name

When the nitrogen is substituted, This is indicated by
prefixing the name of the simple acid amide by N-, or
N,N- followed by the name of the substituent group
 O O
H C NH2 H 3C C NH2
Com. Formamide Com. Acetamide
IUPAC Methanamide IUPAC Ethanamide

O O
H3CH2C C NH2 C NH2
Com. Propionamide
IUPAC propanamide Benzamide

H3C O H3 C O
H3C C C NH2 H3C CH C NH2
H 3C
2-Methylpropanamide
2,2-Dimethylpropanamide
 O O
CH3 CH3
H C N CH3 C N
H
CH3

Com. N,N-Dimethyl formamide Com. N-Methyl acetamide

IUPAC N,N-Dimethyl methanamide IUPAC N-Methyl ethanamide

O O
CH3 H
CH3-CH-CH2 C N CH3-CH-CH2 C N
H3C CH3 CH3
Cl

Com. N,N-Dimethyl iso-valeramide

Com. N-Methyl-3-chlorobutyramide
IUPAC N,N,3-Trimethyl butanamide IUPAC N-Methyl-3-chlorobutanamide
 Acid Halides
• Nomenclature:
They are named acyl halides in both common and IUPAC
systems by dropping the suffix –ic from the name of the
parent acid and adding the suffix –yl. The halide name
is then added as a second word.
O
O
CH3 C Cl
H C Cl

Com. Formyl chlodide Com. Acetyl chloride

IUPAC Methanoyl chloride IUPAC Ethanoyl chloride
 O Cl
O C

CH3-CH2-CH-C-Br C
O Cl
Br
Com. 8-Bromobutyryl bromide Oxalyl chloride
IUPAC 2-Bromobutanoyl bromide

Acid Anhydrides
Acid anhydrides are derived from acids by removing water
molecule from two carboxyl groups and connecting the
fragments. They are named by replacing the word acid in the
name of the parent acid to anhydride
 O
O O C
CH3-C-O-C-CH3 O
Com. Acetic anhydride C
IUPAC Ethanoic anhydride
O
Phthalic anhydride
O Phthalic anhydride
C
O
O O
C CH3-C-O-C-H
O
Formic acetic anhydride
Methanoic ethanoic anhydride
Com. Benzoic anhydride
IUPAC Benzoic anhydride
 Acid Nitriles (Alkyl Cyanides)
They have the general structural formula R-CN
Nomenclature:
1) Common names:
They are given the same name of the acid they give on hydrolysis
by changing the ending thus:

-ic acid -onitrile -oic acid

2) IUPAC name:
They named as alkanonitriles
 CH3-CN CH3-CH2-CN CH3-CH2-CH2-CN

Com. Acetonitrile Propionitrile Butyronitrile

IUPAC Ethanenitrile Propanenitrile Butanenitrile

CH3-CH-CH2CN CH3-CH-CH2-CH2-CN

Br Cl
Com. B-Bromobutyronitrile &-chlorovaleronitrile
IUPAC 3-Bromobutanenitrile 4-chloropentanenitrile
 Amines
• Amines are organic relatives of ammonia by replacing one
or two or three hydrogen with organic groups(R or Ar).
• They are basic
• They are classified as follows:

H-N-R R-N-R R-N-R

H H R
Primary Secondary Tertiary
(1ry) (2ry) (3ry)
• The Nitrogen atom in amine trivalent and carries unshared
electrons pair
•Nomenclature:
1) Common names: name as alkylamine

CH3-CH2-NH2 CH3-CH2-NH-CH2-CH3 Ph-CH2-NH-CH2-CH3

Ethylamine Diethylamine Ethyl benzylamine
(1ry) (2ry)

2) IUPAC name:
• 1ry amine named as aminoalkane
• 2ry and 3ry amines named by using a prefix that includes
all but the longest carbon chain
 CH3-CH2-NH2 CH3-CH-CH2-CH2-CH3
NH2
Aminoethane
2-Aminopentane

CH2CH3
CH3-N-CH2-CH2-CH3 CH3-NH-CH2-CH2-CH3

1-(Ethyl methylamino)propane 1-Mrthylaminopropane

3) Chemical Abstracts (CA) names: Named as alkanamines

CH3CH2CH2NH2 CH3CH2CHCH2CH3
Propanamine N(CH3)2

CH3 CH3 N,N-Dimethyl-3-pentanamine

N

CH3CHCH2CH2CH3

NHCH3
N,N-Dimethylcyclohexanamine N-Methyl-2-pentanamine
* When other functional groups are present, the amino
group is named as a substituent
O
CH3CHCH2COOH NH2-CH2-CH2-C-CH2-CH3
NH2
1-Amino-3-pentanone
3-aminobutanoic acid

• Aromatic amines are named as derivatives of aniline (Common name)

Aminobenzene (IUPAC) and benzenamine (CA name)
NH2 NH2
NHCH3

CH3
Br

Com. Aniline p-Bromoaniline m-Methyl-N-methylaniline

IUPAC Aminobenzene 4-Bromobenzene 3-Methyl-N-methylaminobenzene
CA Benaenamine 4-Bromobenzenamine N-Methyl-3-methylbenaenamine
* Other amines can generally be named by using the prefix
amino-
COOH
SO3H
N(CH3)2

NH2

p-Aminobenzoic acid o-(Dimethylamino)benzene sulphonic acid

4-Aminobenzoic acid 2-(Dimethylamino)benzene sulphonic acid

Other amines have trivial name that have received more use than IUPAC
name CH3 SO3H
OMe COOH
NH2 NH2

NH2 NH2
p-Toluidine o-Anisidine Sulphanilic acid Anthranilic acid