Ésteres. Ejercicios Resueltos

Ésteres. Ejercicios Resueltos

Los ésteres son compuestos orgánicos producidos por la reacción de los alcoholes con los ácidos. Al reaccionar un ácido orgánico o inorgánico, con un alcohol o fenol, se elimina agua y se forma un éster en el que el hidrógeno ácido ha sido reemplazado por un radical orgánico.

La fórmula general de los ésteres es: R-CO-O-R’

Ácido + Alcohol / Fenol ↔ éster + agua

CH3-CH2-COOH + CH3-OH ⇔ CH3-CH2-COO-CH3 + H2O

                           ácido propiónico + metanol   ⇔    propianato de metilo + agua

Cuando la reacción se da en sentido directo se le conoce como esterificación y cuando se da en sentido inverso se le llama saponificación. Cuando se realiza con un ácido orgánico, es conveniente utilizar ácido sulfúrico o ácido clorhídrico como catalizadores.

Propiedades físicas 
  • Son líquidos volátiles que poseen olores agradables a frutas. Son más volátiles que los alcoholes y ácidos de igual masa molar.
  • Son poderosos disolventes
  • Poseen puntos de ebullición muchísimo más bajos que los ácidos carboxílicos de igual masa molar.
Aplicaciones y usos

Como se señaló anteriormente, los ésteres poseen olores agradables a frutas; por tal razón, son utilizados para la preparación de esencias y perfumes artificiales. Al ser poderosos disolventes, son empleados en la elaboración de barnices y en la extracción de antibióticos a partir de licores fermentados.

Los ésteres se encuentran distribuidos ampliamente en los reinos vegetal y animal. Su mayor fuente natural es seguramente las grasas y los aceites, que son ésteres derivados de ácidos grasos de largas cadenas (16 a 18 átomos de carbono) y de la glicerina. Debido a esto se utilizan en la elaboración de jabones mediante el proceso de saponificación.

Tabla. 1. Olores de los ésteres más comunes

Nombre

Olor

Acetato de n-amilo

Banana

Acetato de n-octilo

Naranja

butirato de metilo

Piña

Butirato de n-amilo

Albaricoque

Butirato de isoamilo

Pera

Isovalerato de isoamilo

Manzana

Formiato de isobutilo

Frambuesa

Fuente: Dr.H.Moreno González. Química Orgánica Moderna. 

 

Nomenclatura para Ésteres 

Nomenclatura IUPAC: Alcanoato de alquilo

Nomenclatura Común: Carboxilato de alquilo

Como sustituyente:

-CO-O-R’  Carboalquiloxi (se omite il de 1 a 4 átomos de carbonos) Por ejemplo:

1 átomo de carbono: carbometoxi

5 átomos de carbono: carbopentiloxi

Orden de prioridad. Estos tienen prioridad frente a los alcoholes, aldehídos, cetonas y demás grupos funcionales que están por debajo, sin embargo, los ácidos presentan mayor prioridad sobre los ésteres.

 

Ejercicios Resuelto

IUPAC: Etanoato de etilo

Común: Acetato de etilo

 

2.

IUPAC: Metanoato de propilo

Común: Formiato de n-propilo

 

3.

IUPAC: Hexanoato de 3,3-dimetilbutilo

Común: Caproato de neohexilo

 

4.

IUPAC: ácido- 3- carbo-2-butoxipropanoico

Común: ácido-3- carbo-secbutoxipropiónico

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