Esters
Download
1 / 83

Esters - PowerPoint PPT Presentation


  • 144 Views
  • Uploaded on
  • Presentation posted in: General

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.

loader
I am the owner, or an agent authorized to act on behalf of the owner, of the copyrighted work described.
capcha

Download Presentation

Esters

An Image/Link below is provided (as is) to download presentation

Download Policy: Content on the Website is provided to you AS IS for your information and personal use and may not be sold / licensed / shared on other websites without getting consent from its author.While downloading, if for some reason you are not able to download a presentation, the publisher may have deleted the file from their server.


- - - - - - - - - - - - - - - - - - - - - - - - - - E N D - - - - - - - - - - - - - - - - - - - - - - - - - -

Presentation Transcript


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


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


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


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


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


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


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..


preparation


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


NOMENCLATURE


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.


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


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


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


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


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


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


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


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


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


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


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


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


Tutti

fruity


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


APPLICATIONS


FOOD

flavoring


COSMETICS

flavoring


BEVERAGES

flavoring


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


MEDICINE


SYNTHETIC

fibers


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.


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


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


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


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

19

20

13

11

18

17

16

01

15

14

07

08

03

04

05

12

09

10

06

02

00

O

C – O ־Na+

O

C – O – H

+ H2O

+ Na – OH

Benzoic acid

Sodium benzoate


J

U

M

B

L

E

D

L

E

T

T

E

R

S


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.


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.


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.


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.


CHEMICAL

properties


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


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


Example

O

ethylphenylethanoate

CH3 – C – O –

CH2 – CH3

+ H – OH

O

H+

CH3 – C – OH+

HO

CH2 – CH3

Acetic acid

4 - ethylphenol


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


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


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


PHYSICAL

properties


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


ad
  • Login