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Quimica Organica
Jabones/tensioactivos/detergen
tes/soap

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Recordemos Acidos carboxilicos

O
H

Estructura de Lewis del acido formico

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Propiedades fisicas de acidos

carboxilicos

Acidos carboxilicos son polares:

O
CH3

C+

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Propiedades fisicas de acidos

carboxilicos

Carboxylic acids pueden formar puentes
hidrogeno:
+

O
CH3

H O

C
O

H+
+

CH3

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Propiedades fsicas de los cidos

carboxilicos
Carboxylic acids also interact with water
molecules by hydrogen bonding through both the
carboxyl oxygen and the hydroxyl group.
H
O

O H

CH3
H

O
O

H
H

H O Copyright 2010 PearsonO H

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Preparation of Carboxylic Acids

Oxidation of Primary Alcohols

CH3(CH2)5CH2OH

H2CrO4

1-heptanol

O
CH3(CH2)5COH
heptanoic acid

O
HOCH2CH2CH2CH2OH

KMnO4

1,4-butanediol

HOCCH2CH2COH
butanedioic acid

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Acidity of Carboxylic Acids

All carboxylic acids, whether soluble or
insoluble in water, react quantitatively with
NaOH, KOH, and other strong bases to
form salts
CO2H

CO2

+ NaOH
benzoic acid
levemente soluble en agua
(only slightly soluble in H 2 O)

Na
+ H 2O

sodium benzoate
soluble en agua
(very soluble in water)

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Acidity of Carboxylic Acids

Carboxylic acids solo reaccionan con bases
debiles como el bicarbonato de sodio para
formar sales
CO2 K

CO2 K
H C OH
HO C H
CO2H

+ NaHCO3
sodium bicarbonate
(baking soda)

H C OH
HO C H

+ CO2 + H2O

CO2 Na

potassium hydrogen tartrate

(cream of tartar)

Baking powder: una mezcla de bicarbonato de sodio con tartrato acido

de potasio. Cuando se aade agua, la parte acida de la sal del tartrato
reacciona , y se libera dioxido de carbono.

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Derivatives of Carboxylic Acids

O
C

O
Cl

an acid chloride

an anhydride
O

O
C

an ester

R
an amide
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Reacciones de esteres

Hidrolisis
Los Esteres son normalmente no-reactivos con
agua.
Sin embargo, en presencia de acidos (aq. HCl
or H2SO4) o bases (NaOH or KOH), pueden
hidrolizarse

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Hidrlisis Catalizada por cidos

El reverso de la esterificacin de Fischer:
O
CH3

CH2CH3 + H2O

O
CH3

+ HOCH2CH3
OH

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Base-Promoted Hidrolisis
promovida por bases

Esta reacci es usada para la obtencion de
jabones
O
CH3

CH2CH3 + NaOH

H2O

O
CH3

O Na

+ HOCH2CH3

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Mechanism of Saponification

Step One Nucleophilic addition of
hydroxide anion:
O

O
CH3

OH
O

CH3

CH2CH3

C OCH CH
2
3
OH

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Mechanism of Saponification

Step One Nucleophilic addition of
hydroxide anion:
O

O
CH3

OH
O

CH2CH3

CH3

C OCH CH
2
3
OH

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Mechanism of Saponification

Step Two Elimination of alkoxide anion:

O
CH3

C OCH CH
2
3
OH

O
CH3

H +

OCH2CH3

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Mechanism of Saponification

Step Two Elimination of alkoxide anion:

O
CH3

C OCH CH
2
3
OH

O
CH3

H +

OCH2CH3

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Mechanism of Saponification

Step Three Proton reorganization (acid
base reaction):
O
CH3

H +

OCH2CH3
O
CH3

+ HOCH2CH3

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Mechanism of Saponification

Step Three Proton reorganization (acid
base reaction):
O
CH3

H +

OCH2CH3
O
CH3

+ HOCH2CH3

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Ejemplo Problema

Complete the following reaction:
O
CH3

hydrolysis in
aqueous acid
O
O

H3O
CH3

+ HO
OH

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Ejemplo Problema

Complete the following reaction:
O
CH3

hydrolysis in
aqueous acid
O
O

H3O
CH3

+ HO
OH

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Sample Problem

Complete the following reaction:
O
CH3

CH2

CH2

CH3 saponification in
aqueous NaOH

O
O
NaOH
H2O

CH3

O Na

+ HOCH2CH2OH

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Sample Problem

Complete the following reaction:
O
CH3

CH2

CH2

CH3 saponification in
aqueous NaOH

O
O
NaOH
H2O

CH3

O Na

+ HOCH2CH2OH

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Sample Problem

Complete the following reaction:
O
CH3

CH2

CH2

CH3 saponification in
aqueous NaOH

O
O
NaOH
H2O

CH3

O Na

+ HOCH2CH2OH

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Soaps/ Jabones
Sodium stearate/ estereato de Na:

ionic
(hydrophilic)

hydrocarbon
(hydrophobic)

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Soaps/ Jabones a partir de grasa

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Soap/Jabon
La micela de Jabn:
Na

Na
Na

H2O

Na

O2C

H2O

H2O

Na
CO2

CO2

O2C

Na

CO2

H2O

Na
CO2

O2C

Na

Na
O2C

H2O

H2O

CO2
O2C

Na

Na

O2C
O2C

O2C

CO2

CO2

Na

Na

H2O

Na

Na

H2O

Na

Soap
A soap micelle:
Na

Na

H2O

Na
Na

H2O

O2C

H2O

Na
CO2

CO2

O2C

Na

CO2

H2O

Na
CO2

O2C

Na

Na

Hidrofobica

O2C

H2O

CO2

O2C
Na

H2O
Na

O2C
O2C

O2C

CO2

CO2

Hidrofilica
Na

Na

H2O

Na

H O

Na

2
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Na

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Soap
A soap micelle:
Na

Na

H2O

Na

H2O

Na
O2C

H2O

Na
CO2

CO2

O2C

Na

CO2

H2O

Na

Mancha
grasa

CO2

O2C

Na

Na
O2C

H2O

CO2
O2C

Na

H2O
Na

O2C
O2C

O2C

CO2

CO2
Na

Na

H2O

Na

H O

Na

2
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Na

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Objetivo: Mejorar propiedades detersivas del agua

poca de sumerios (3000 a.c) se usaba azufre jabonoso para cura de
enfermedades.
Leblanc (1987) : Procedimiento para obtencion de jabon a escala
industrial ( Quimica industrial de tensioactivos moderna)
Siglos XIX y XX se amplio la gama de derivados del jabon.
Crecimento del uso de fibras sinteticas ( celulosa; acetatos,etc.).
Gnter (BASF-1917): alquilacin y sulfonacin de naftaleno; pero
el alquilnaftaleno sulfonato sin caracter tensiactivo suficiente.
Bertsch y col ( 1927): Mediante sulfatacin de un alcohol graso
obtuvieron 1detergente sintetico..materias primas renovables?
Henkel(1932)

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LAS

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Algunas propiedades de los tensioactivos son:

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Clasificacin de los detergentes (tensioactivos):

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Ejemplo de formacion de un detergente anionico

OH
H2SO4
cold
OSO3H
NaOH
O
O

S
O

O Na

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Ejemplo de formacion de un detergente anionico

OH
H2SO4
cold
OSO3H
NaOH
O
hydrophobic

S
O

hydrophilic

O Na

Sodium dodecyl sulfate

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Detergentes anionicos
Alkyl benzene sulfonate detergents (ABS)
Non-biodegradable

hydrophobic

hydrophilic

O Na

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