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Esters. Identify the family of organic compound under CARBONYL group and give the IUPAC & COMMON name D’ structure. 19. 20. 13. 11. 18. 17. 16. 01. 15. 14. 07. 08. 03. 04. 05. 12. 09. 10. 06. 02. 00. O ║. Lactic Acid . CH 3 – CH – C – OH . OH.

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Esters

Esters


Esters

Identify the family of organic compound

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

19

20

13

11

18

17

16

01

15

14

07

08

03

04

05

12

09

10

06

02

00

O

Lactic Acid

CH3 – CH – C – OH

OH

2 – hydroxypropanoic acid


Esters

Identify the family of organic compound

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

19

20

13

11

07

14

15

08

16

17

18

01

10

03

05

04

09

12

06

02

00

O

C

3HC

CH3

3,3 – dimethylbenzophenone


Esters

Identify the family of organic compound

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

19

20

13

11

18

17

16

01

15

14

07

08

03

04

05

12

09

10

06

02

00

O

C – H

CH3 – (CH2)3 – C – CH – CH3

2 – isopropylhexanal

CH3

α – isopropylcaproaldehyde


Esters

Identify the family of organic compound

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

19

20

13

11

15

14

08

07

18

17

16

01

06

03

12

04

09

05

10

00

02

O

C – OH

Cl

Cl

O

HO – C

O

C – OH

Cl

2,4,6 – trichloro – 1,3,5 – benzenetricarboxylic acid


Esters

Identify the family of organic compound

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

19

20

13

11

07

14

15

08

16

17

18

01

10

03

05

04

09

12

06

02

00

HO

O

C – CH3

3HC

3 – hydroxy – 5 – methylacetophenone


Esters

Identify the family of organic compound

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

19

20

13

11

18

17

16

01

15

14

07

08

03

04

05

12

09

10

06

02

00

O

C – H

CH3 – C – CH2 – CH – CH2 – CH3

3HC

(CH2)2 – CH3

4 – ethyl – 2,2 – dimethylheptanal

γ – ethyl – α,α – dimethylenanthaldehyde


Esters

ESTERS


Esters

An esteris an organic compound that is formed when an alcohol reacts with an acid.

FANCYFRUITYFRAGRANTESTERS:Esters are chemicals that have distinctive (usually pleasant) aromas..


Esters

preparation


Esters

ESTERIFICATION

GEN. FORMULA

Carboxylic acid + Alcohol → ESTER + Water

H+/ heat

Example

O

O

H+/ heat

CH3 – C – OH + H –O – CH3

CH3 – C – O – CH3 + H2O

Acetic acid

methanol

methyl acetate

methyl ethanoate


Esters

NOMENCLATURE


Iupac rules

IUPACRULES

  • 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.


Esters

STRUCTURE 1

19

20

13

11

07

14

15

08

16

17

18

01

10

03

05

04

09

12

06

02

00

O

CH3 – (CH2)2 – C – O – CH2 – CH3

ethyl butanoate

ethyl butyrate


Esters

STRUCTURE 2

19

20

13

11

16

01

18

17

08

14

15

07

09

06

03

12

04

05

10

02

00

O

CH3 – (CH2)2 – C – O – CH2 - SH

methylthiobutanoate

methylthio butyrate


Esters

19

20

13

11

STRUCTURE 3

16

01

18

17

08

14

15

07

09

06

03

12

04

05

10

02

00

O

CH3 – (CH2)2 – C – O –– CH3

methyl butanoate

methyl butyrate


Esters

19

20

13

11

STRUCTURE 4

16

01

18

17

08

14

15

07

09

06

03

12

04

05

10

02

00

O

CH3 – C – O – (CH2)7 – CH3

octylethanoate

octyl acetate


Esters

STRUCTURE 5

19

20

13

11

16

01

18

17

08

14

15

07

09

06

03

12

04

05

10

02

00

O

C – O – CH3

NH2

methyl – 2 – aminobenzoate

2 – (aminomethyl) benzoate


Esters

STRUCTURE 6

19

20

13

11

15

14

08

07

18

17

16

01

12

04

09

05

10

06

03

02

00

O

CH3

CH3 – C – O – (CH2)2 – CH – CH3

isoamylethanoate

isoamyl acetate


Esters

19

20

13

11

18

17

16

01

15

14

07

08

10

03

04

12

06

09

05

STRUCTURE 7

02

00

O

CH3 – (CH2)2 – C – O – CH2 –

benzyl butanoate

benzyl butyrate


Esters

STRUCTURE 8

19

20

13

11

15

14

08

07

18

17

16

01

12

04

09

05

10

06

03

02

00

O

CH3

H – C – O – CH2 – CH – CH3

isobutyl methanoate

isobutyl formate


Esters

19

20

13

11

STRUCTURE 9

16

01

18

17

08

14

15

07

09

06

03

12

04

05

10

02

00

O

CH3 – C – O – CH2 –

benzyl ethanoate

benzyl acetate


Esters

19

20

13

11

STRUCTURE 10

16

01

18

17

08

14

15

07

09

06

03

12

04

05

10

02

00

O

CH3 – (CH2)2 – C – O – (CH2)4 – CH3

pentylbutanoate

pentyl butyrate


Esters

19

20

13

11

STRUCTURE 11

16

01

18

17

08

14

15

07

09

06

03

12

04

05

10

02

00

O

CH3 – C – O – (CH2)2 – CH3

propylethanoate

propyl acetate


Esters

STRUCTURE 12

19

20

13

11

15

14

08

07

18

17

16

01

12

04

09

05

10

06

03

02

00

O

C – O

CH2 – CH3

ethyl benzoate

ethyl benzoate


Esters

Tutti

fruity


Esters

19

20

13

11

STRUCTURE 13

15

14

08

07

18

17

16

01

12

04

09

05

10

06

03

02

00

O

CH3 – C – O –

CH2 – CH3

ethylphenylethanoate

ethylphenyl acetate


Esters

APPLICATIONS


Esters

FOOD

flavoring


Esters

COSMETICS

flavoring


Esters

BEVERAGES

flavoring


Esters

19

20

13

11

STRUCTURE 14

16

01

18

17

08

14

15

07

09

06

03

12

04

05

10

02

00

O

H – C – O – CH2 – CH3

ethyl methanoate

ethyl formate


Esters

MEDICINE


Esters

SYNTHETIC

fibers


Esters

ENERGY

fuel


Assignments

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.


Esters

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

19

20

13

11

15

14

08

07

18

17

16

01

06

03

12

04

09

05

10

00

02

O

CH3 – (CH2)2 – C – H

O

CH3 – (CH2)2 – C – OH

K2Cr2O7

--------→

(O)

butanal

butanoic acid

butyric acid


Esters

Do a reaction to produce ISOPROPYL ALCOHOL or 2 - propanol an industrial solvent.

19

20

13

11

18

17

16

01

15

14

07

08

10

03

04

06

09

12

05

02

00

OH

O

Pt

CH3 – CH–CH3

CH3 – C – CH3

+ H – H

--------→

ACETONE

2 - PROPANOL

Isopropyl Alcohol


Esters

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

19

20

13

11

15

14

08

07

18

17

16

01

03

04

09

12

05

06

10

02

00

O

C – OH

H+/ heat

+ H – O – CH3

methyl alcohol

OH

O

C – O – CH3

Salicylic acid

+ H2O

methyl salicylate

OH


Esters

Do a reaction to produce SODIUM BENZOATE a carboxylic acid salt used as industrial preservative.

19

20

13

11

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17

16

01

15

14

07

08

03

04

05

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09

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06

02

00

O

C – O ־Na+

O

C – O – H

+ H2O

+ Na – OH

Benzoic acid

Sodium benzoate


Esters

J

U

M

B

L

E

D

L

E

T

T

E

R

S


Esters

00

01

02

03

04

05

06

07

08

09

10

C

H

Y

P

L

A

I

S

T

R

O

P

P

E

R

I

E

S

CLUE:

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


Esters

00

01

02

03

04

05

06

07

08

10

09

N

O

T

I

F

I

C

A

P

S

A

I

N

O

CLUE:

A reaction that results to breaking of ester linkage.


Esters

00

10

09

07

06

08

04

03

02

01

05

M

E

C

H

A

L

I

C

T

R

O

P

P

E

R

I

E

S

CLUE:

oxidation; hydrogenation; esterification; neutralization.


Esters

00

01

02

03

04

05

06

07

08

10

09

Y

L

H

Y

D

R

I

S

O

S

CLUE:

A reaction that involves water.


Esters

CHEMICAL

properties


Esters

HYDROLYSIS

GEN. FORMULA

ESTERS + Water ↔Carboxylic acid + Alcohol/Phenol

H+

Example

Butanoic acid

O

O

H+

CH3 – (CH2)2 – C – O – CH2 – CH3

+ H – OH

CH3 – (CH2)2 – C – OH

ethyl butanoate

+ H – O – CH2 – CH3

ethyl butyrate

ethyl alcohol


Esters

Examples

Salicylic acid

O

C – OH

O

C – O – CH3

H+

+ H – OH

OH

OH

Methanol

methyl salicylate

+ H – O – CH3

Acetic acid

O

O

H+

+ H – OH

CH3 – C – OH

CH3 – C – O – (CH2)7 – CH3

+ H – O – (CH2)7 – CH3

Octyl acetate

octanol


Esters

Example

O

ethylphenylethanoate

CH3 – C – O –

CH2 – CH3

+ H – OH

O

H+

CH3 – C – OH+

HO

CH2 – CH3

Acetic acid

4 - ethylphenol


Esters

SAPONIFICATION

GEN. FORMULA

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

Example

Sodium butyrate

O

O

CH3 – (CH2)2 – C – O –– CH3

+ Na – OH

CH3 – (CH2)2 – C – O – Na +

methyl butyrate

+ HO –– CH3

Methanol


Esters

Examples

Lithium ethanoate

O

O

CH3 – C – O – (CH2)2 – CH3

+ Li – OH

CH3 – C – O ־Li+

Propylethanoate

propanol

+ HO – (CH2)2 – CH3

potassium benzoate

O

C – O־K+

O

C – O – CH3

+ K – OH

+ HO – CH3

Methyl benzoate

methanol


Esters

Example

O

CH3

CH3 – C – O – (CH2)2 – CH – CH3

+ Na – OH

isoamylethanoate

3 – methyl – 1 - butanol

O

CH3

CH3 – C – O – ־Na+

+

HO– (CH2)2 – CH – CH3

Sodium ethanoate

isopentyl alcohol


Esters

PHYSICAL

properties


Only one of its kind

ONLY ONE OF ITS KIND

  • 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.


Table of comparison

Table of Comparison


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