alcoholes fenoles_omarambi_2012
DESCRIPTION
Alcoholes y FenolesTRANSCRIPT
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Basado en el texto “Química Orgánica John mcMurry, 5°ed. 2001
por óscar g. marambio
Alcoholes y Fenoles
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Alcoholes y Fenoles
Los alcoholes contienen un grupo hidroxilo OH enlazado a un átomo de
carbono con hibridazación sp3.
Los alcoholes son importantes solventes e intermediarios en síntesis
orgánica.
Los fenoles contienen un grupo hidroxilo OH enlazado a un átomo de
carbono de un anillo aromático.
Ambos se pueden considerar como derivados orgánicos del agua:
H – O – H versus R – O – H o Ar – O – H
Nota: los enoles se han excluido de este capítulo, porque sus propiedades
químicas son demasiado diferentes. Se veran con más detalle en otros
capítulo.
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Metanol (CH3OH)
Etanol (CH3CH2OH)
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Fenoles
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17.1
Nombre de algunos alcoholes y fenoles
Clasificación de los alcoholes:
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Ejemplos de nomenclatura IUPAC
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Ejercicios:
Respuesta: (a) 5-metil-2,4-hexanodiol, (b) 2-metil-4-fenil-2-butanol, (c) 4,4-
dimetilciclohexanol, (d) trans-2-bromociclopentanol, (e) 4-bromo-3-
metilfenol
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17.2
Propiedades de alcoholes y fenoles:
enlace hidrógeno
Propiedades físicas:
Fenoles
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Alcoholes sencillos
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Enlace de hidrógeno:
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17.3
Propiedades de los alcoholes acidez y basicidad
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(Ácido más débil)
(Ácido más fuerte)
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Acidez relativa de los alcoholes
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Efecto inductivo
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Formación de alcóxido desde los alcoholes
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Formación de alcóxido desde los alcoholes
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Acidez de los fenoles
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para
orto orto
orto
para
meta meta
orto
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Este efecto solo debe ser considerado en las posiciones orto y para
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Ejemplo grupo atractor de electrones
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HC≡CH < (CH3)2CHOH < CH3OH < (CF3)2CHOH
P-metilfenol < fenol < p-(trifluorometil)fenol
Alcohol bencílico < fenol < ácido p-hidroxibenzoico
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17.4
Preparación de alcoholes: repaso
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Recordemos algunos métodos de preparación de
alcoholes: hidratación regioespecífica de alquenos
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Ejercicios:
Respuesta
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Oxidación y reducción en química orgánica
Antes de seguir nuestro estudio de la química de alcoholes es conveniente
detenernos para repasar algunos conceptos básicos, que ustedes deberán
recordar, por ello veremos brevemente el concepto de oxidación y
reducción en química orgánica.
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Ejemplos:
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Más ejemplos:
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Solución problemas 10.13 y 10.14
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17.5
Alcoholes por reducción de compuestos
carbonílicos
Mecanismo de reducción del carbonilo:
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Reducción de aldehídos y cetonas para producir
alcoholes
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Ejemplo de reducción con NaBH4 de aldehído y cetonas
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Ejemplo de reducción con LiAlH4 de aldehído y cetonas
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Ejemplo de reducción de ácidos carboxílicos y ésteres
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Ejercicios:
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Solución problemas 17.7 y 17.8
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17.6
Alcoholes por reducción de compuestos
carbonílicos con el reactivo de Grignard
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Limitaciones del reactivo de Grignard
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Mecanismo de adición del reactivo de Grignard
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Ejercicio:
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Tarea:
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17.7
Algunas reacciones de los alcoholes
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Deshidratación para producir alquenos
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Dos electrones del átomo de oxígeno se unen a H+ y
producen un alcohol protonado intermediario
Se rompe el enlace carbono – oxígeno y los dos
electrones del enlace permanecen con el oxígeno;
esto deja un carbocatión intermediario.
Dos electrones de un enlace carbono – hidrógeno
vecino forman el enlace p de un alqueno y se
elimina H+ (un protón).
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El grupo hidroxilo del alcohol reacciona con POCl3
para formar un diclorofosfato intermediario
Se efectúa la eliminación E2 por el mecanismo usual
en una etapa en que la piridina abstrae un protón del
carbono vecino al mismo tiempo que sale el grupo
diclorofosfato
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Conversión de alcoholes en halogenuros de alquilo
Alcoholes terciarios:
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El carbocatión reacciona con el ion cloruro y da el
producto cloruro de alquilo
La pérdida espontánea de agua da un carbocatión
intermediario.
La protonación del oxígeno del alcohol al reaccionar
con HCl da un ion oxonio, el cual experimenta una
reacción SN1
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Alcoholes primarios y secundarios
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Primero: Se debe convertir el alcohol en tosilatos: ruptura del enlace O-H
Conversión de alcohol en éter, utilizando tosilatos
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Conversión de alcohol en éter, utilizando tosilatos
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Conversion of Alcohols into Esters
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17.8
Oxidación de alcoholes
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17.9
Protección de alcoholes
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+
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17.10
Preparación y uso de los fenoles
Ejemplos de otros fenoles de uso común:
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Síntesis de algunos fenoles
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17.11
Reacciones de los fenoles
OH
+ CH3 CH CH3
Cl OH
CH3 CH3
CH3
CH3
CH3
CH3
AlCl3
3
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FIN
GRACIAS
Octubre, 2012