Esters

181716000102030405060708091011121314152019Identify the family of organic compound

under CARBONYL group and give the IUPAC & COMMON name D’ structure.

CH3 – CH – C – OH

O║

OH2 – hydroxypropanoic acid

Lactic Acid

181716000102030405060708091011121314152019Identify the family of organic compound

under CARBONYL group and give the IUPAC or COMMON name D’ structure.

O║C

3HC CH3

3,3 – dimethylbenzophenone

181716000102030405060708091011121314152019

CH3 – (CH2)3 – C – CH – CH3

O║C – H

CH3

Identify the family of organic compound under CARBONYL group and give the IUPAC &

COMMON name D’ structure.

2 – isopropylhexanal

α – isopropylcaproaldehyde

181716000102030405060708091011121314152019Identify the family of organic compound

under CARBONYL group and give the IUPAC or COMMON name D’ structure.

O ║ C – OH

O ║ C – OH

O ║ HO – C

ClCl

Cl2,4,6 – trichloro – 1,3,5 – benzenetricarboxylic acid

181716000102030405060708091011121314152019Identify the family of organic compound

under CARBONYL group and give the IUPAC or COMMON name D’ structure.

3 – hydroxy – 5 – methylacetophenone

O ║ C – CH3 3HC

HO

181716000102030405060708091011121314152019Identify the family of organic compound

under CARBONYL group and give the IUPAC & COMMON name D’ structure.

CH3 – C – CH2 – CH – CH2 – CH3

O║C – H

3HC (CH2)2 – CH3 4 – ethyl – 2,2 – dimethylheptanal

γ – ethyl – α,α – dimethylenanthaldehyde

ESTERS

FANCY FRUITY FRAGRANT ESTERS: Esters are chemicals that have distinctive (usually pleasant)

aromas..

An ester is an organic compound that is formed when an

alcohol reacts with an acid.

preparation

ESTERIFICATIONGEN. FORMULA

Carboxylic acid + Alcohol → ESTER + WaterH+/ heat

Example

CH3 – C – OH + H – O – CH3

O║

Acetic acid

H+/ heatCH3 – C – O – CH3 + H2O

O║

methyl acetatemethanol

methyl ethanoate

NOMENCLATURE

• An ESTER is named as two words.• The first word is the alkyl group attached to

the oxygen of the ESTER group.• The ending ic acid will be replaced with the

suffix ate. • The common name which is used more often

uses the common name of the carboxylic acid.

IUPAC RULES

181716000102030405060708091011121314152019

CH3 – (CH2)2 – C – O – CH2 – CH3

O║

STRUCTURE 1

ethyl butanoate

ethyl butyrate

181716000102030405060708091011121314152019

CH3 – (CH2)2 – C – O – CH2 - SH

O║

methylthio butanoatemethylthio butyrate

STRUCTURE 2

181716000102030405060708091011121314152019

CH3 – (CH2)2 – C – O –– CH3

O║

methyl butanoate

methyl butyrate

STRUCTURE 3

181716000102030405060708091011121314152019

CH3 – C – O – (CH2)7 – CH3

O║

octyl ethanoate

octyl acetate

STRUCTURE 4

181716000102030405060708091011121314152019

methyl – 2 – aminobenzoate

O║C – O – CH3

NH2

2 – (aminomethyl) benzoate

STRUCTURE 5

181716000102030405060708091011121314152019

CH3 – C – O – (CH2)2 – CH – CH3

O║

CH3

isoamyl ethanoate

isoamyl acetate

STRUCTURE 6

181716000102030405060708091011121314152019

CH3 – (CH2)2 – C – O – CH2 –

O║

benzyl butanoate

benzyl butyrate

STRUCTURE 7

181716000102030405060708091011121314152019

H – C – O – CH2 – CH – CH3

O║

CH3

isobutyl methanoateisobutyl formate

STRUCTURE 8

181716000102030405060708091011121314152019

CH3 – C – O – CH2 –

O║

benzyl ethanoate

benzyl acetate

STRUCTURE 9

181716000102030405060708091011121314152019

CH3 – (CH2)2 – C – O – (CH2)4 – CH3

O║

pentyl butanoate

pentyl butyrate

STRUCTURE 10

181716000102030405060708091011121314152019

CH3 – C – O – (CH2)2 – CH3

O║

propyl ethanoate

propyl acetate

STRUCTURE 11

181716000102030405060708091011121314152019

ethyl benzoate

C – O

O║

CH2 – CH3

ethyl benzoate

STRUCTURE 12

Tuttifruity

181716000102030405060708091011121314152019

ethylphenyl ethanoate

ethylphenyl acetate

CH3 – C – O –

O║

CH2 – CH3

STRUCTURE 13

APPLICATIONS

FOODflavoring

COSMETICSflavoring

BEVERAGESflavoring

181716000102030405060708091011121314152019

H – C – O – CH2 – CH3

O║

ethyl methanoateethyl formate

STRUCTURE 14

MEDICINE

SYNTHETICfibers

ENERGY

fuel

Assignments• What are physical & chemical

properties of organic compound ESTERS?• Cite some industrial applications of

their chemical reactions.• References: All organic chemistry

book will do.

181716000102030405060708091011121314152019 O ║CH3 – (CH2)2 – C – H --------→

O ║CH3 – (CH2)2 – C – OH K2Cr2O7

butanal butanoic acid

Do a reaction to produce BUTYRIC ACID or BUTANOIC ACID a carboxylic acid found in rancid butter.

butyric acid

(O)

181716000102030405060708091011121314152019Do a reaction to produce ISOPROPYL ALCOHOL or 2 - propanol an

industrial solvent.

CH3 – C – CH3

O ║

--------→ + H – H CH3 – CH – CH3 Pt

OH

ACETONE 2 - PROPANOL

Isopropyl Alcohol

181716000102030405060708091011121314152019O║C – OH

OH

Salicylic acid

+ H – O – CH3

methyl alcohol

H+/ heat

O║C – O – CH3

OH

+ H2O

methyl salicylate

Do a reaction to produce METHYL SALICYLATE the main components of paste form painkillers.

181716000102030405060708091011121314152019Do a reaction to produce SODIUM BENZOATE a carboxylic acid salt used as

industrial preservative.

O║C – O – H

Benzoic acid

+ Na – OH

O║C – O ־Na+ + H2O

Sodium benzoate

J U M B L E D

L E T T E R S

0001020304050607080910

PR P SEIO ET R

Solubility; Boiling Point; Melting Point; Polarity & Acidity.CLUE:

Y PH SA IC

P R O P E R T I E S

L

P H Y S I C A L

0001020304050607080910P SO IAI F CTN A

A reaction that results to breaking of ester linkage.

CLUE:

I ON

S A P O N I F I C A T I O N

0001020304050607080910

PR P SEIO ET R

oxidation; hydrogenation; esterification; neutralization.CLUE:

EM H L CAC

P R O P E R T I E S

I

C H E M I C A L

0001020304050607080910DYL OR SY IH

A reaction that involves water.

CLUE:

S

H Y D R O L Y S I S

CHEMICALproperties

HYDROLYSIS

ESTERS + Water ↔ Carboxylic acid + Alcohol/PhenolH+

GEN. FORMULA

Example

CH3 – (CH2)2 – C – O – CH2 – CH3

O║

ethyl butanoate

ethyl butyrate

+ H – OH H+

CH3 – (CH2)2 – C – OH

O║

Butanoic acid

+ H – O – CH2 – CH3

ethyl alcohol

Examples

O║C – O – CH3

OH

Salicylic acid

+ H – OH H+

O║C – OH

OH

+ H – O – CH3 methyl salicylate Methanol

CH3 – C – O – (CH2)7 – CH3

O║

Octyl acetate

H+CH3 – C – OH

O║

Acetic acid

octanol

+ H – OH

+ H – O – (CH2)7 – CH3

CH3 – C – O –

O║

ethylphenyl ethanoate

CH2 – CH3

Example

+ H – OH

H+ CH3 – C – OH +

O║

HO CH2 – CH3 Acetic acid

4 - ethylphenol

SAPONIFICATIONGEN. FORMULA

ESTERS + Base ----→ Carboxylate salt + Alcohol

Example

CH3 – (CH2)2 – C – O –– CH3

O║

+ Na – OH

methyl butyrate

CH3 – (CH2)2 – C – O – Na +

O║

Sodium butyrate

+ HO –– CH3

Methanol

Examples

CH3 – C – O – (CH2)2 – CH3

O║

+ Li – OH

Propyl ethanoateCH3 – C – O ־Li+

propanol

O║C – O – CH3

Methyl benzoate

+ K – OH

O║C – O ־K+

potassium benzoate

Lithium ethanoateO║

+ HO – (CH2)2 – CH3

+ HO – CH3

methanol

CH3 – C – O – (CH2)2 – CH – CH3

O║

CH3

isoamyl ethanoate

Example

+ Na – OH

CH3 – C – O – ־Na+

O║

Sodium ethanoate+ HO – (CH2)2 – CH – CH3

CH3

isopentyl alcohol

3 – methyl – 1 - butanol

PHYSICALproperties

• PHYSICAL STATE: Lower molecular weighted esters are colorless volatile liquids. Higher esters are colorless waxy solids.

• ODOR: All esters have a strong fruity smell.• SOLUBILITY: Lower members of esters are soluble

in water. The solubility decreases with increase in molecular weight of the esters. Esters are soluble in organic solvents. Esters themselves are good organic solvents.

• ACIDIC NATURE: Esters are neutral to litmus tests.

ONLY ONE OF ITS KIND

CLASS COMPOUND WEIGHT BOILING

Alkane pentane 72 35 °C

Ether Diethyl ether 74 35 °C

Aldehyde butanal 72 76 °C

Alcohol 1 - butanol 74 118 °C

Carboxylic acid

Propanoic acid

74 141 °C

ESTER Ethyl formate 74 108 °C

Table of Comparison