ORIENT COLLEGES TALAGANG

BSc Chemistry-II Paper C

On-Screen Lectures
Nomenclature of Organic Compounds
Lecture # 15
 Esters and Salts of Carboxylic Acids

When H atom of –COOH is replaced by an alkyl

group, it gives rise to another class called esters

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Carboxylic Acids R-COOH Esters RCOO-R`
R & R` may be
same or different

 Esters have general formula RCOOR` where R may be H-atom or

alkyl group or a ring but R` may be an alkyl group or a ring but it
cannot be H

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 Esters and Salts of Carboxylic Acids

When H atom of –COOH is replaced by a cation,

the compounds are called salts of carboxylic acids

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Carboxylic Acids R-COOH Salts of RCOO-Mx+
Carboxylic acids Where Mx+ is a
cation having a
specific charge

 Salts of Carboxylic acids have general formula RCOOMx+ where M

is a cation having a specific charge x+
 e.g RCOONa+ are called sodium salts of carboxylic acids e.g.
HCOONa, CH3COONa
 e.g RCOONK+ are called potassium salts of carboxylic acids e.g.
HCOOK, CH3COOK
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 Common or Trivial Names of Esters and Salts of Carboxylic
Acids

Common names of esters and salts of carboxylic

acids are two-word

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 Name of alkyl group attached to O-atom (Or name of cation in
case of salts) is written
 Name of remaining group is obtained by replacing “ic acid”
from name of parent carboxylic acid with “ate”

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 Common or Trivial Names of Esters and Salts of Carboxylic
Acids

Carboxylic Acids Name Esters/ Salts of Name

Carboxylic acids
HCOOH Formic Acid HCOOCH3 Methyl Formate

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CH3COOH Acetic Acid CH3COOC2H5 Ethyl Acetate
CH3CH2CH2COOH Butyric acid CH3CH2CH2COO-Na+ Sodium Butyrate
HCOOH Formic Acid HCOONa+ Sodium formate
CH3COOH Acetic Acid CH3COOK+ Potassium Acetate
HOOC-COOH Oxalic acid H3COOC-COOCH3 Dimethyl Oxalate
HOOC-CH2-CH2-COOH Succinic acid K+OOC-CH2-CH2-COOK+ Dipotassium succinate
CH3-(CH2)4-COOH Caproic acid CH3-(CH2)4-COOCH3 Methyl Caproate
C6H5COOH Benzoic acid C6H5COONa+ Sodium benzoate

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 Common or Trivial Names of Esters and Salts of Carboxylic
Acids

Carboxylic Acids Name Esters/ Salts of Carboxylic Name

acids
Adipic Acid Diethyl

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Adipate

Glutamic Sodium
acid glutamate

Oxalic acid Potassium

oxalate

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 Common or Trivial Names of Esters and Salts of Carboxylic
Acids

Carboxylic Acids Name Esters/ Salts of Carboxylic Name

acids
Benzoic Sodium

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acid benzoate

Phthalic Diethyl
acid phthalate

Terephthali Diethyl
c acid terephthala
te

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 IUPAC Names of Esters and Salts
of Carboxylic Acids
1. Select the longest C-chain containing the –COO- group. This is called
parent chain. All groups outside this chain are called substituents
Number the C-atoms of chain. –COO- is always situated at one end. So

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2.
numbering is always started from C of –COO- group
3. Name the substituents in alphabetical order prefixed by their position.
e.g. 5-ethyl
4. If a substituent occurs more than one time, use prefixes di, tri, tetra etc.
to indicate two, three, four or many times occurrence. e.g. 2,3-dimethyl
or 4,4-diethyl
5. Write name of alkyl group attached to O-atom (or name of cation in
case of salts) proceeded by ALKANOATE obtained by replacing “e”
from name of alkane corresponding to number of C-atoms in the parent
chain with “oate”

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 IUPAC Names of Esters and Salts
of Carboxylic Acids

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 IUPAC Names of Esters and Salts
of Carboxylic Acids

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Sodium Pentanate
1. Write name of cation (sodium)
2. There are five Cs in the chain
3. Name of chain is pentanoate (from pentane)
4. So full name is sodium pentanoate

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 IUPAC Names of Esters and Salts
of Carboxylic Acids

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Methyl 4-methylpentanoate
1. Write name of alkyl group attached to O-atom (methyl)
2. There are five Cs in the chain
3. There is methyl at C-4 so write 4-methyl
4. Name of chain is pentanoate (from pentane)
5. So full name is Methyl 4-methylpentanoate
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 IUPAC Names of Esters and Salts
of Carboxylic Acids

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Methyl 4-methylpentanoate
1. Write name of alkyl group attached to O-atom (methyl)
2. There are five Cs in the chain
3. There is methyl at C-4 so write 4-methyl
4. Name of chain is pentanoate (from pentane)
5. So full name is Methyl 4-methylpentanoate
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 IUPAC Names of Esters and Salts
of Carboxylic Acids

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Potassium Propanoate
1. Write name of cation (potassium)
2. There are three Cs in the chain
3. There is no substituent
4. Name of chain is propanoate (from propane)
5. So full name is potassium propanoate
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 IUPAC Names of Esters and Salts
of Carboxylic Acids

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Ethyl hexanoate
1. Write name of alkyl group attached to O-atom (ethyl)
2. There are six Cs in the chain
3. There is no substituent
4. Name of chain is hexanoate (from hexane)
5. So full name is ethyl hexanoate
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 IUPAC Names of Esters and Salts
of Carboxylic Acids

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Ethyl 3-phenylpropanoate
1. Write name of alkyl group attached to O-atom (ethyl)
2. There are three Cs in the chain
3. There is phenyl at C-3 so write 3-phenyl
4. Name of chain is propanoate (from propane)
5. So full name is ethyl 3-phenylpropanoate
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 IUPAC Names of Esters and Salts
of Carboxylic Acids

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Diethyl butanedioate
1. Write name of alkyl group attached to O-atoms (diethyl)
2. There are four Cs in the chain
3. Name of chain is butanedioate (from butane)
4. So full name is diethyl butanedioate

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 IUPAC Names of Esters and Salts of
Carboxylic Acids
Practice Questions
Write common names of esters/ salts of carboxylic acids

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 IUPAC Names of Esters and Salts of
Carboxylic Acids
Practice Questions
Write common names of esters/ salts of carboxylic acids

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 IUPAC Names of Esters and Salts of
Carboxylic Acids
Practice Questions
Write common names of esters/ salts of carboxylic acids

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 IUPAC Names of Esters and Salts of
Carboxylic Acids
Practice Questions
Write IUPAC names of esters/ salts of carboxylic acids

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 Interesting Information
 Many esters have fruity smell or characteristic fragrance
due to which they are used as artificial flavors to give
flavors to food items and in production of perfumes

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 Interesting Information
Ester name Odor or Ester name Odor or occurrence
occurrence
Allyl hexanoate pineapple Ethyl benzoate sweet, wintergreen, fruity,
medicinal, cherry, grape
Butyl propanoate pear drops Ethyl butyrate banana, pineapple, strawberry

Butyl butyrate pineapple Ethyl hexanoate pineapple, waxy-green banana

Benzyl acetate pear, strawberry, Ethyl cinnamate cinnamon

jasmine
Bornyl acetate pine Ethyl formate lemon, rum, strawberry

Butyl acetate apple, honey Ethyl heptanoate apricot, cherry, grape,

raspberry

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 Interesting Information
Ester name Odor or Ester name Odor or occurrence
occurrence
Geranyl acetate geranium Linalyl acetate lavender, sage
Geranyl butyrate cherry Linalyl butyrate peach
Geranyl pentanoate apple Linalyl formate apple, peach
Isobutyl acetate cherry, Methyl acetate glue
raspberry,
strawberry
Isobutyl formate raspberry Methyl grape, jasmine
anthranilate
Isopropyl acetate fruity

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 Interesting Information
Ester name Odor or Ester name Odor or occurrence
occurrence
Nonyl caprylate orange Propyl acetate pear
Octyl acetate fruity-orange Propyl blackberry, pineapple,
hexanoate cheese, wine
Octyl butyrate parsnip Propyl rum
isobutyrate
Amyl acetate apple, banana Terpenyl cherry
(pentyl acetate) butyrate
Pentyl butyrate apricot, pear,
(amyl butyrate) pineapple

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