Tema 3 - Carbonilo - Qmc 302
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Transcript of Tema 3 - Carbonilo - Qmc 302
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Tema nº 3 Tema nº 3
QUIMICA DEL CARBONILOQUIMICA DEL CARBONILO
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Aldehidos y cetonasAldehidos y cetonas
La mayoria de las
reacciones
proceden por el
mecanismo de
adición
nucleofílica al
grupo carbonilo
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Acidos carboxilicos
Los ácidos carboxílicos y sus derivados proceden por el
mecanismo de sustitución acil nucleofílica al grupo
carbonilo.
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SUSTITUCIÓN ACIL NUCLEOFILICA
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Aldehidos y cetonas pueden ser sustituidos en su posición alfaSustitución alfa-carbonilo
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SUSTITUCIÓN ALFA-CARBONILO
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TAUTOMERIA CETOENÓLICA
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Formación y estabilidad de los iones enolato
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Reacciones de condensación carbonílica
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REACCIONES DE CONDENSACIÓN
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3.1. Adicion nucleofilica al CO
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3.2. Sustitución Acil Nucleofílica
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Diagrama energético
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Esterificacion fischer
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Esterificación con Diazometano
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Interconversión de derivados de ácido
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Grupos salientes
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Problemas
1. Proponga un mecanismo de trans-esterificación
de apertura de anillo
2. Proponga un mecanismo, catalizada por un ácido
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Reordenamiento del ácido benzílico
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PROPONGA MECANISMOS
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3.3. Substitución alfa - carbonílo
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Problema
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Problemas de estudio
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3.4. Mecanismos de Condensacion Carbonílica
Condensación por sustitución SN2
3.4.1. Condensación por sustitución
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ProblemaPredecir el producto formado y el mecanismo por el cual se produjo
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Adición de carbono nucleofílico al carbonilo
2.4.2. Condensación de cetonas y aldehídos
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Condensación del etanal en medio ácido
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Problema
Análisis
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Proponer el mecanismo de la ciclación aldólica
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ProblemaPredecir el producto de las siguientes reacciones
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Sustitución Acil nucleofílica al grupo acilo por el carbanión alfa
3.4.3. Condensación de Claisen de ésteres
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Mecanismo genérico
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Condensación de Dieckmann- un tipo de ciclación de Claisen
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ProblemaPrediga los productos de las siguientes condensaciones de Claisen Cruzadas
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Problemas avanzadosLa reacción de Darzens involucra una condensación base catalizada de dos pasos, el primer paso es una reaccion de condensación carbonílica y el segundo es una reacción SN2, desacriba ambos pasos y muestre sus mecanismos
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Reacción de Michael : Adición conjugada al carbonilo
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Problema
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ProblemaProponga mecanismos para las siguientes reacciones
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Ejemplo
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Problema
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Condensación de Perkin
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Condensación de Knoevenagel
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ProblemaProponer el mecanismo de la reaccion
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Problemas avanzados