Preparation of Alkynes: Dehydrohalogenation | Organic Chemistry | JoVE (Translated to Spanish)

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Capítulo 0: Alquinos Back To Chapter

JoVE Core Organic Chemistry Chapter 9.5: Prepararación de alquinos: Deshidrohalogenación

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CONTENIDOS

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Capítulo 0: Enlace covalente y estructura

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JoVE Core Organic Chemistry Chapter 1.1: ¿Qué es la química orgánica?
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JoVE Core Organic Chemistry Chapter 1.2: Estructura electrónica de los átomos
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JoVE Core Organic Chemistry Chapter 1.3: Configuraciones electrónicas
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JoVE Core Organic Chemistry Chapter 1.4: Enlaces químicos
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JoVE Core Organic Chemistry Chapter 1.5: Enlaces covalentes polares
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JoVE Core Organic Chemistry Chapter 1.6: Las Estructuras de Lewis y Las Cargas Formales
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JoVE Core Organic Chemistry Chapter 1.7: Teoría RPECV
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JoVE Core Organic Chemistry Chapter 1.8: Geometría molecular y Momentos dipolo
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JoVE Core Organic Chemistry Chapter 1.9: Resonancia y Estructuras Híbridas
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JoVE Core Organic Chemistry Chapter 1.10: Teoría del enlace de valencia y los orbitales híbridos
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JoVE Core Organic Chemistry Chapter 1.11: Teoría MO y Enlaces Covalentes
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JoVE Core Organic Chemistry Chapter 1.12: Fuerzas Intermoleculares y Propiedades Físicas
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JoVE Core Organic Chemistry Chapter 1.13: Solubilidad
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JoVE Core Organic Chemistry Chapter 1.14: Introducción a los grupos funcionales
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JoVE Core Organic Chemistry Chapter 1.15: Visión general de los Grupos Funcionales Avanzados

Capítulo 0: Termodinámica y cinética química

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JoVE Core Organic Chemistry Chapter 2.1: Reacciones Químicas
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JoVE Core Organic Chemistry Chapter 2.2: Entalpía y Calor de Reacción
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JoVE Core Organic Chemistry Chapter 2.3: Energética de la formación de soluciones
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JoVE Core Organic Chemistry Chapter 2.4: Entropía y Solvatación
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JoVE Core Organic Chemistry Chapter 2.5: Energía libre de Gibbs y Favorabilidad termodinámica
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JoVE Core Organic Chemistry Chapter 2.6: Equilibrio químico y de solubilidad
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JoVE Core Organic Chemistry Chapter 2.7: Ley de velocidad y Orden de reacción
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JoVE Core Organic Chemistry Chapter 2.8: Efecto del cambio de temperatura en la velocidad de la reacción
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JoVE Core Organic Chemistry Chapter 2.9: Reacciones de múltiples pasos
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JoVE Core Organic Chemistry Chapter 2.10: Energía de disociación de enlace y energía de activación
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JoVE Core Organic Chemistry Chapter 2.11: Diagramas de energía, Estados de transición e Intermediarios
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JoVE Core Organic Chemistry Chapter 2.12: Predicción del rendimiento de una reacción

Capítulo 0: Alcanos y cicloalcanos

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JoVE Core Organic Chemistry Chapter 3.1: Estructura de los Alcanos
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JoVE Core Organic Chemistry Chapter 3.2: Isómeros Constitucionales de los Alcanos
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JoVE Core Organic Chemistry Chapter 3.3: Nomenclatura de los Alcanos
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JoVE Core Organic Chemistry Chapter 3.4: Propiedades físicas de los Alcanos
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JoVE Core Organic Chemistry Chapter 3.5: Proyecciones de Newman
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JoVE Core Organic Chemistry Chapter 3.6: Conformaciones del Etano y el Propano
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JoVE Core Organic Chemistry Chapter 3.7: Conformaciones del Butano
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JoVE Core Organic Chemistry Chapter 3.8: Cicloalcanos
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JoVE Core Organic Chemistry Chapter 3.9: Conformaciones de los Cicloalcanos
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JoVE Core Organic Chemistry Chapter 3.10: Conformaciones del ciclohexano
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JoVE Core Organic Chemistry Chapter 3.11: Conformación en silla del Ciclohexano
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JoVE Core Organic Chemistry Chapter 3.12: Estabilidad de Ciclohexanos Sustituidos
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JoVE Core Organic Chemistry Chapter 3.13: Ciclohexanos Disustituidos: Isomería cis-trans
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JoVE Core Organic Chemistry Chapter 3.14: Energía de combustión: Una medida de estabilidad en los alcanos y cicloalcanos

Capítulo 0: Estereoisomería

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JoVE Core Organic Chemistry Chapter 4.1: Quiralidad
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JoVE Core Organic Chemistry Chapter 4.2: Isomería
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JoVE Core Organic Chemistry Chapter 4.3: Estereoisomería
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JoVE Core Organic Chemistry Chapter 4.4: Nombrando a los Enantiomeros
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JoVE Core Organic Chemistry Chapter 4.5: Propiedades de los Enantiomeros y Actividad Óptica
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JoVE Core Organic Chemistry Chapter 4.6: Moléculas con múltiples centros quirales
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JoVE Core Organic Chemistry Chapter 4.7: Proyecciones de Fischer
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JoVE Core Organic Chemistry Chapter 4.8: Mezclas Racémicas y la Resolución de Enantiomeros
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JoVE Core Organic Chemistry Chapter 4.9: Estereoisomería de los compuestos cíclicos
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JoVE Core Organic Chemistry Chapter 4.10: Quiralidad en el Nitrógeno, Fósforo y Azúfre
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JoVE Core Organic Chemistry Chapter 4.11: Proquiralidad
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JoVE Core Organic Chemistry Chapter 4.12: La quiralidad en la naturaleza

Capítulo 0: Ácidos y Bases

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JoVE Core Organic Chemistry Chapter 5.1: Ácidos y Bases de Brønsted-Lowry
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JoVE Core Organic Chemistry Chapter 5.2: Ácidos y Bases de Lewis
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JoVE Core Organic Chemistry Chapter 5.3: Ácidos y Bases: Ka, pKa y Fuerzas relativas
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JoVE Core Organic Chemistry Chapter 5.4: Posición del equilibrio en las reacciones Ácido-Base
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JoVE Core Organic Chemistry Chapter 5.5: Estructura molecular y acidez
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JoVE Core Organic Chemistry Chapter 5.6: El efecto nivelador y las soluciones ácido-base no acuosas
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JoVE Core Organic Chemistry Chapter 5.7: Efectos solvatadores

Capítulo 0: Reacciones de sustitución nucleofílica y eliminación de haluros de alquilo

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JoVE Core Organic Chemistry Chapter 6.1: Haluros de alquilo
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JoVE Core Organic Chemistry Chapter 6.2: Recciones de sustitución nucleofílica
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JoVE Core Organic Chemistry Chapter 6.3: Nucleófilos
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JoVE Core Organic Chemistry Chapter 6.4: Electrófilos
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JoVE Core Organic Chemistry Chapter 6.5: Grupos salientes
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JoVE Core Organic Chemistry Chapter 6.6: Carbocationes
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JoVE Core Organic Chemistry Chapter 6.7: Reacción SN2: Cinética
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JoVE Core Organic Chemistry Chapter 6.8: Reacción SN2: Mecanismo
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JoVE Core Organic Chemistry Chapter 6.9: Reacción SN2: Estado de transición
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JoVE Core Organic Chemistry Chapter 6.10: Reacción SN2: Estereoquímica
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JoVE Core Organic Chemistry Chapter 6.11: Reacción SN1: Cinética
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JoVE Core Organic Chemistry Chapter 6.12: Reacción SN1: Mecanismo
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JoVE Core Organic Chemistry Chapter 6.13: Reacción SN1: Estereoquímica
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JoVE Core Organic Chemistry Chapter 6.14: Prediciendo los productos: SN1 vs. SN2
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JoVE Core Organic Chemistry Chapter 6.15: Reacciones de eliminación
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JoVE Core Organic Chemistry Chapter 6.16: Reacción E2: Cinética y Mecanismo
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JoVE Core Organic Chemistry Chapter 6.17: Reacción E2: Estereoquímica y Regioquímica
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JoVE Core Organic Chemistry Chapter 6.18: Reacción E1: Cinética y Mecanismo
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JoVE Core Organic Chemistry Chapter 6.19: Reacción E1: Estereoquímica y Regioquímica
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JoVE Core Organic Chemistry Chapter 6.20: Prediciendo los productos: Sustitución vs. Eliminación

Capítulo 0: Estructura y reactividad de los alquenos

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JoVE Core Organic Chemistry Chapter 7.1: Estructura y enlace de los alquenos
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JoVE Core Organic Chemistry Chapter 7.2: Nomenclatura de los alquenos
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JoVE Core Organic Chemistry Chapter 7.3: Grado de insaturación
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JoVE Core Organic Chemistry Chapter 7.4: Isomería en los alquenos
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JoVE Core Organic Chemistry Chapter 7.5: Estabilidades relativas de los alquenos
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JoVE Core Organic Chemistry Chapter 7.6: Introducción a las reacciones de adición electrofílica de los alquenos
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JoVE Core Organic Chemistry Chapter 7.7: Regioselectividad de las adiciones electrofílicas a los alquenos: Regla de Markovnikov

Capítulo 0: Reacciones de los alquenos

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JoVE Core Organic Chemistry Chapter 8.1: Regioselectividad de las adiciones electrofílicas - Efecto peróxido
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JoVE Core Organic Chemistry Chapter 8.2: Reacción en cadena de radicales libres y polimerización de alquenos
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JoVE Core Organic Chemistry Chapter 8.3: Halogenación de alquenos
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JoVE Core Organic Chemistry Chapter 8.4: Formación de halohidrina a partir de alquenos
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JoVE Core Organic Chemistry Chapter 8.5: Hidratación de alquenos catalizada por ácido
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JoVE Core Organic Chemistry Chapter 8.6: Regioselectividad y estereoquímica de la hidratación catalizada por ácido
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JoVE Core Organic Chemistry Chapter 8.7: Oximercuriación-Reducción de alquenos
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JoVE Core Organic Chemistry Chapter 8.8: Hidroboración-Oxidación de Alquenos
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JoVE Core Organic Chemistry Chapter 8.9: Regioselectividad y estereoquímica de la hidroboración
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JoVE Core Organic Chemistry Chapter 8.10: Oxidación de alquenos: Dihidroxilación syn con Tetraóxido de Osmio
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JoVE Core Organic Chemistry Chapter 8.11: Oxidación de alquenos: Dihidroxilación syn con permanganato de potasio
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JoVE Core Organic Chemistry Chapter 8.12: Oxidación de alquenos: Anti dihidroxilación con peroxiácidos
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JoVE Core Organic Chemistry Chapter 8.13: Escisión oxidativa de los alquenos: Ozonólisis
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JoVE Core Organic Chemistry Chapter 8.14: Reducción de alquenos: Hidrogenación catalítica
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JoVE Core Organic Chemistry Chapter 8.15: Reducción de alquenos: Hidrogenación catalítica asimétrica

Capítulo 0: Alquinos

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JoVE Core Organic Chemistry Chapter 9.1: Estructura y propiedades físicas de los alquinos
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JoVE Core Organic Chemistry Chapter 9.2: Nomenclatura de los alquinos
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JoVE Core Organic Chemistry Chapter 9.3: Acidez de los 1-alquinos
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JoVE Core Organic Chemistry Chapter 9.4: Preparación de alquinos: Reacción de alquilación
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JoVE Core Organic Chemistry Chapter 9.5: Prepararación de alquinos: Deshidrohalogenación
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JoVE Core Organic Chemistry Chapter 9.6: Adición electrofílica a alquinos: Halogenación
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JoVE Core Organic Chemistry Chapter 9.7: Adición electrofílica a alquinos: Hidrohalogenación
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JoVE Core Organic Chemistry Chapter 9.8: Alquinos a Aldehídos y Cetonas: Hidratación catalizada por ácido
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JoVE Core Organic Chemistry Chapter 9.9: Alquinos a Aldehídos y Cetonas: Hidroboración-Oxidación
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JoVE Core Organic Chemistry Chapter 9.10: Alquinos a Ácidos carboxílicos: Escisión oxidativa
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JoVE Core Organic Chemistry Chapter 9.11: Reducción de Alquinos a cis-alquenos: Hidrogenación catalítica
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JoVE Core Organic Chemistry Chapter 9.12: Reducción de alquinos a trans-alquenos: Sodio en amonio líquido

Capítulo 0: Alcoholes y fenoles

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JoVE Core Organic Chemistry Chapter 10.1: Estructura y Nomeclatura de Alcoholes y Fenoles
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JoVE Core Organic Chemistry Chapter 10.2: Propiedades Físicas de los Alcoholes y Fenoles
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JoVE Core Organic Chemistry Chapter 10.3: Acidez y Basicidad de Alcoholes y Fenoles
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JoVE Core Organic Chemistry Chapter 10.4: Preparación de Alcoholes Mediante Reacciones de Adición
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JoVE Core Organic Chemistry Chapter 10.5: Preparación de alcoholes mediante reacciones de sustitución
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JoVE Core Organic Chemistry Chapter 10.6: Deshidratación catalizada por ácido de alcoholes a alquenos
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JoVE Core Organic Chemistry Chapter 10.7: Alcoholes a partir de compuestos carbonilo: Reducción
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JoVE Core Organic Chemistry Chapter 10.8: Alcoholes a partir de compuestos carbonilo: Reacción de Grignard
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JoVE Core Organic Chemistry Chapter 10.9: Protección de alcoholes
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JoVE Core Organic Chemistry Chapter 10.10: Preparación de Dioles y Reordenamiento Pinacol
30
JoVE Core Organic Chemistry Chapter 10.11: Conversión de alcoholes a Haluros de Alquilo
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JoVE Core Organic Chemistry Chapter 10.12: Oxidación de alcoholes

Capítulo 0: Éteres, Epóxidos, Sulfuros

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JoVE Core Organic Chemistry Chapter 11.1: Estructura y Nomenclatura de los Éteres
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JoVE Core Organic Chemistry Chapter 11.2: Propiedades Físicas de los Éteres
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JoVE Core Organic Chemistry Chapter 11.3: Éteres a partir de Alcoholes: Deshidratación de Alcoholes y Síntesis de Éter de Williamson
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JoVE Core Organic Chemistry Chapter 11.4: Éteres a partir de alquenos: Adición de alcohol y alcoximercuración-desmercuración
30
JoVE Core Organic Chemistry Chapter 11.5: De Éteres a Haluros de alquilo: Escisión ácida
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JoVE Core Organic Chemistry Chapter 11.6: Auto-oxidación de Éteres en Peróxidos e Hidroperóxidos
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JoVE Core Organic Chemistry Chapter 11.7: Éteres corona
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JoVE Core Organic Chemistry Chapter 11.8: Estructura y Nomenclatura de los Epóxidos
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JoVE Core Organic Chemistry Chapter 11.9: Preparación de Epóxidos
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JoVE Core Organic Chemistry Chapter 11.10: Epoxidación de Sharpless
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JoVE Core Organic Chemistry Chapter 11.11: Apertura de Anillo de Epóxidos Catalizada por Ácido
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JoVE Core Organic Chemistry Chapter 11.12: Apertura de Anillo de Epóxidos Catalizada por Base
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JoVE Core Organic Chemistry Chapter 11.13: Estructura y Nomenclatura de Tioles y Sulfuros
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JoVE Core Organic Chemistry Chapter 11.14: Preparación y Reacciones de Tioles
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JoVE Core Organic Chemistry Chapter 11.15: Preparación y Reacciones de Sulfuros

Capítulo 0: Aldehydes and Ketones

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JoVE Core Organic Chemistry Chapter 12.1: Structures of Aldehydes and Ketones
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JoVE Core Organic Chemistry Chapter 12.2: IUPAC Nomenclature of Aldehydes
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JoVE Core Organic Chemistry Chapter 12.3: IUPAC Nomenclature of Ketones
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JoVE Core Organic Chemistry Chapter 12.4: Common Names of Aldehydes and Ketones
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JoVE Core Organic Chemistry Chapter 12.5: IR and UV–Vis Spectroscopy of Aldehydes and Ketones
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JoVE Core Organic Chemistry Chapter 12.6: NMR Spectroscopy and Mass Spectrometry of Aldehydes and Ketones
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JoVE Core Organic Chemistry Chapter 12.7: Preparation of Aldehydes and Ketones from Alcohols, Alkenes, and Alkynes
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JoVE Core Organic Chemistry Chapter 12.8: Preparation of Aldehydes and Ketones from Nitriles and Carboxylic Acids
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JoVE Core Organic Chemistry Chapter 12.9: Preparation of Aldehydes and Ketones from Carboxylic Acid Derivatives
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JoVE Core Organic Chemistry Chapter 12.10: Nucleophilic Addition to the Carbonyl Group: General Mechanism
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JoVE Core Organic Chemistry Chapter 12.11: Aldehydes and Ketones with Water: Hydrate Formation
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JoVE Core Organic Chemistry Chapter 12.12: Aldehydes and Ketones with Alcohols: Hemiacetal Formation
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JoVE Core Organic Chemistry Chapter 12.13: Protecting Groups for Aldehydes and Ketones: Introduction
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JoVE Core Organic Chemistry Chapter 12.14: Acetals and Thioacetals as Protecting Groups for Aldehydes and Ketones
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JoVE Core Organic Chemistry Chapter 12.15: Aldehydes and Ketones with HCN: Cyanohydrin Formation Overview
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JoVE Core Organic Chemistry Chapter 12.16: Aldehydes and Ketones with HCN: Cyanohydrin Formation Mechanism
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JoVE Core Organic Chemistry Chapter 12.17: Aldehydes and Ketones to Alkenes: Wittig Reaction Overview
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JoVE Core Organic Chemistry Chapter 12.18: Aldehydes and Ketones to Alkenes: Wittig Reaction Mechanism
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JoVE Core Organic Chemistry Chapter 12.19: Aldehydes and Ketones with Amines: Imine and Enamine Formation Overview
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JoVE Core Organic Chemistry Chapter 12.20: Aldehydes and Ketones with Amines: Imine Formation Mechanism
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JoVE Core Organic Chemistry Chapter 12.21: Aldehydes and Ketones with Amines: Enamine Formation Mechanism
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JoVE Core Organic Chemistry Chapter 12.22: Aldehydes and Ketones to Alkanes: Wolff–Kishner Reduction
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JoVE Core Organic Chemistry Chapter 12.23: Oxidations of Aldehydes and Ketones to Carboxylic Acids
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JoVE Core Organic Chemistry Chapter 12.24: Reactions of Aldehydes and Ketones: Baeyer–Villiger Oxidation
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JoVE Core Organic Chemistry Chapter 12.25: Keto–Enol Tautomerism: Mechanism

Capítulo 0: Carboxylic Acids

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JoVE Core Organic Chemistry Chapter 13.1: IUPAC Nomenclature of Carboxylic Acids
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JoVE Core Organic Chemistry Chapter 13.2: Physical Properties of Carboxylic Acids
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JoVE Core Organic Chemistry Chapter 13.3: Acidity of Carboxylic Acids
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JoVE Core Organic Chemistry Chapter 13.4: Substituent Effects on Acidity of Carboxylic Acids
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JoVE Core Organic Chemistry Chapter 13.5: IR and UV–Vis Spectroscopy of Carboxylic Acids
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JoVE Core Organic Chemistry Chapter 13.6: NMR and Mass Spectroscopy of Carboxylic Acids
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JoVE Core Organic Chemistry Chapter 13.7: Preparation of Carboxylic Acids: Overview
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JoVE Core Organic Chemistry Chapter 13.8: Preparation of Carboxylic Acids: Hydrolysis of Nitriles
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JoVE Core Organic Chemistry Chapter 13.9: Preparation of Carboxylic Acids: Carboxylation of Grignard Reagents
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JoVE Core Organic Chemistry Chapter 13.10: Reactions of Carboxylic Acids: Introduction
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JoVE Core Organic Chemistry Chapter 13.11: Carboxylic Acids to Esters: Acid-Catalyzed (Fischer) Esterification Overview
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JoVE Core Organic Chemistry Chapter 13.12: Carboxylic Acids to Esters: Acid-Catalyzed (Fischer) Esterification Mechanism
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JoVE Core Organic Chemistry Chapter 13.13: Carboxylic Acids to Methylesters: Alkylation using Diazomethane
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JoVE Core Organic Chemistry Chapter 13.14: Carboxylic Acids to Acid Chlorides
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JoVE Core Organic Chemistry Chapter 13.15: Carboxylic Acids to Primary Alcohols: Hydride Reduction
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JoVE Core Organic Chemistry Chapter 13.16: Loss of Carboxy Group as CO2: Decarboxylation of β-Ketoacids
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JoVE Core Organic Chemistry Chapter 13.17: Loss of Carboxy Group as CO2: Decarboxylation of Malonic Acid Derivatives

Capítulo 0: Carboxylic Acid Derivatives

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JoVE Core Organic Chemistry Chapter 14.1: Carboxylic Acid Derivatives: Overview
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JoVE Core Organic Chemistry Chapter 14.2: Nomenclature of Carboxylic Acid Derivatives: Acid Halides, Esters, and Acid Anhydrides
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JoVE Core Organic Chemistry Chapter 14.3: Nomenclature of Carboxylic Acid Derivatives: Amides and Nitriles
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JoVE Core Organic Chemistry Chapter 14.4: Structures of Carboxylic Acid Derivatives
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JoVE Core Organic Chemistry Chapter 14.5: Physical Properties of Carboxylic Acid Derivatives
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JoVE Core Organic Chemistry Chapter 14.6: Acidity and Basicity of Carboxylic Acid Derivatives
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JoVE Core Organic Chemistry Chapter 14.7: Spectroscopy of Carboxylic Acid Derivatives
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JoVE Core Organic Chemistry Chapter 14.8: Relative Reactivity of Carboxylic Acid Derivatives
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JoVE Core Organic Chemistry Chapter 14.9: Nucleophilic Acyl Substitution of Carboxylic Acid Derivatives
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JoVE Core Organic Chemistry Chapter 14.10: Acid Halides to Carboxylic Acids: Hydrolysis
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JoVE Core Organic Chemistry Chapter 14.11: Acid Halides to Esters: Alcoholysis
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JoVE Core Organic Chemistry Chapter 14.12: Acid Halides to Amides: Aminolysis
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JoVE Core Organic Chemistry Chapter 14.13: Acid Halides to Alcohols: LiAlH4 Reduction
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JoVE Core Organic Chemistry Chapter 14.14: Acid Halides to Alcohols: Grignard Reaction
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JoVE Core Organic Chemistry Chapter 14.15: Acid Halides to Ketones: Gilman Reagent
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JoVE Core Organic Chemistry Chapter 14.16: Preparation of Acid Anhydrides
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JoVE Core Organic Chemistry Chapter 14.17: Reactions of Acid Anhydrides
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JoVE Core Organic Chemistry Chapter 14.18: Esters to Carboxylic Acids: Saponification
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JoVE Core Organic Chemistry Chapter 14.19: Esters to Carboxylic Acids: Acid-Catalyzed Hydrolysis
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JoVE Core Organic Chemistry Chapter 14.20: Esters to Alcohols: Hydride Reductions
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JoVE Core Organic Chemistry Chapter 14.21: Esters to Alcohols: Grignard Reaction
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JoVE Core Organic Chemistry Chapter 14.22: Preparation of Amides
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JoVE Core Organic Chemistry Chapter 14.23: Amides to Carboxylic Acids: Hydrolysis
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JoVE Core Organic Chemistry Chapter 14.24: Amides to Amines: LiAlH4 Reduction
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JoVE Core Organic Chemistry Chapter 14.25: Preparation of Nitriles
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JoVE Core Organic Chemistry Chapter 14.26: Nitriles to Carboxylic Acids: Hydrolysis
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JoVE Core Organic Chemistry Chapter 14.27: Nitriles to Ketones: Grignard Reaction
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JoVE Core Organic Chemistry Chapter 14.28: Nitriles to Amines: LiAlH4 Reduction

Capítulo 0: α-Carbon Chemistry: Enols, Enolates, and Enamines

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JoVE Core Organic Chemistry Chapter 15.1: Reactivity of Enols
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JoVE Core Organic Chemistry Chapter 15.2: Reactivity of Enolate Ions
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JoVE Core Organic Chemistry Chapter 15.3: Types of Enols and Enolates
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JoVE Core Organic Chemistry Chapter 15.4: Enolate Mechanism Conventions
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JoVE Core Organic Chemistry Chapter 15.5: Regioselective Formation of Enolates
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JoVE Core Organic Chemistry Chapter 15.6: Stereochemical Effects of Enolization
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JoVE Core Organic Chemistry Chapter 15.7: Acid-Catalyzed α-Halogenation of Aldehydes and Ketones
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JoVE Core Organic Chemistry Chapter 15.8: Base-Promoted α-Halogenation of Aldehydes and Ketones
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JoVE Core Organic Chemistry Chapter 15.9: Multiple Halogenation of Methyl Ketones: Haloform Reaction
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JoVE Core Organic Chemistry Chapter 15.10: α-Halogenation of Carboxylic Acid Derivatives: Overview
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JoVE Core Organic Chemistry Chapter 15.11: α-Bromination of Carboxylic Acids: Hell–Volhard–Zelinski Reaction
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JoVE Core Organic Chemistry Chapter 15.12: Reactions of α-Halocarbonyl Compounds: Nucleophilic Substitution
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JoVE Core Organic Chemistry Chapter 15.13: Nitrosation of Enols
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JoVE Core Organic Chemistry Chapter 15.14: C–C Bond Formation: Aldol Condensation Overview
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JoVE Core Organic Chemistry Chapter 15.15: Base-Catalyzed Aldol Addition Reaction
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JoVE Core Organic Chemistry Chapter 15.16: Acid-Catalyzed Aldol Addition Reaction
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JoVE Core Organic Chemistry Chapter 15.17: Dehydration of Aldols to Enals: Base-Catalyzed Aldol Condensation
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JoVE Core Organic Chemistry Chapter 15.18: Dehydration of Aldols to Enones: Acid-Catalyzed Aldol Condensation
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JoVE Core Organic Chemistry Chapter 15.19: Intramolecular Aldol Reaction
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JoVE Core Organic Chemistry Chapter 15.20: C–C Bond Cleavage: Retro-Aldol Reaction
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JoVE Core Organic Chemistry Chapter 15.21: Crossed Aldol Reactions: Overview
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JoVE Core Organic Chemistry Chapter 15.22: Crossed Aldol Reaction Using Weak Bases
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JoVE Core Organic Chemistry Chapter 15.23: Ketones with Nonenolizable Aromatic Aldehydes: Claisen–Schmidt Condensation
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JoVE Core Organic Chemistry Chapter 15.24: Crossed Aldol Reaction Using Strong Bases: Directed Aldol Reaction
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JoVE Core Organic Chemistry Chapter 15.25: Aldol Condensation with β-Diesters: Knoevenagel Condensation
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JoVE Core Organic Chemistry Chapter 15.26: Esters to β-Ketoesters: Claisen Condensation Overview
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JoVE Core Organic Chemistry Chapter 15.27: Esters to β-Ketoesters: Claisen Condensation Mechanism
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JoVE Core Organic Chemistry Chapter 15.28: Aldol Condensation vs Claisen Condensation
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JoVE Core Organic Chemistry Chapter 15.29: Intramolecular Claisen Condensation of Dicarboxylic Esters: Dieckmann Cyclization
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JoVE Core Organic Chemistry Chapter 15.30: β-Dicarbonyl Compounds via Crossed Claisen Condensations
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JoVE Core Organic Chemistry Chapter 15.31: α-Alkylation of Ketones via Enolate Ions
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JoVE Core Organic Chemistry Chapter 15.32: Factors Affecting α-Alkylation of Ketones: Choice of Base
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JoVE Core Organic Chemistry Chapter 15.33: Alkylation of β-Ketoester Enolates: Acetoacetic Ester Synthesis
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JoVE Core Organic Chemistry Chapter 15.34: Alkylation of β-Diester Enolates: Malonic Ester Synthesis
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JoVE Core Organic Chemistry Chapter 15.35: Conjugate Addition to α,β-Unsaturated Carbonyl Compounds
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JoVE Core Organic Chemistry Chapter 15.36: Conjugate Addition (1,4-Addition) vs Direct Addition (1,2-Addition)
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JoVE Core Organic Chemistry Chapter 15.37: Conjugate Addition of Enolates: Michael Addition
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JoVE Core Organic Chemistry Chapter 15.38: Cyclohexenones via Michael Addition and Aldol Condensation: The Robinson Annulation
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JoVE Core Organic Chemistry Chapter 15.39: Synthesis of α-Substituted Carbonyl Compounds: The Stork Enamine Reaction
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JoVE Core Organic Chemistry Chapter 15.40: Nonenolizable Aldehydes to Acids and Alcohols: The Cannizzaro Reaction

Capítulo 0: Dienes, Conjugated Pi Systems, and Pericyclic Reactions

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JoVE Core Organic Chemistry Chapter 16.1: Structure of Conjugated Dienes
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JoVE Core Organic Chemistry Chapter 16.2: Stability of Conjugated Dienes
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JoVE Core Organic Chemistry Chapter 16.3: π Molecular Orbitals of 1,3-Butadiene
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JoVE Core Organic Chemistry Chapter 16.4: π Molecular Orbitals of the Allyl Cation and Anion
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JoVE Core Organic Chemistry Chapter 16.5: π Molecular Orbitals of the Allyl Radical
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JoVE Core Organic Chemistry Chapter 16.6: Electrophilic 1,2- and 1,4-Addition of HX to 1,3-Butadiene
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JoVE Core Organic Chemistry Chapter 16.7: Electrophilic 1,2- and 1,4-Addition of X2 to 1,3-Butadiene
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JoVE Core Organic Chemistry Chapter 16.8: Electrophilic Addition of HX to 1,3-Butadiene: Thermodynamic vs Kinetic Control
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JoVE Core Organic Chemistry Chapter 16.9: UV–Vis Spectroscopy of Conjugated Systems
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JoVE Core Organic Chemistry Chapter 16.10: UV–Vis Spectroscopy: Woodward–Fieser Rules
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JoVE Core Organic Chemistry Chapter 16.11: Pericyclic Reactions: Introduction
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JoVE Core Organic Chemistry Chapter 16.12: Thermal and Photochemical Electrocyclic Reactions: Overview
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JoVE Core Organic Chemistry Chapter 16.13: Thermal Electrocyclic Reactions: Stereochemistry
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JoVE Core Organic Chemistry Chapter 16.14: Photochemical Electrocyclic Reactions: Stereochemistry
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JoVE Core Organic Chemistry Chapter 16.15: Cycloaddition Reactions: Overview
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JoVE Core Organic Chemistry Chapter 16.16: Cycloaddition Reactions: MO Requirements for Thermal Activation
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JoVE Core Organic Chemistry Chapter 16.17: Cycloaddition Reactions: MO Requirements for Photochemical Activation
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JoVE Core Organic Chemistry Chapter 16.18: [4+2] Cycloaddition of Conjugated Dienes: Diels–Alder Reaction
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JoVE Core Organic Chemistry Chapter 16.19: Diels–Alder vs Retro-Diels–Alder Reaction: Thermodynamic Factors
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JoVE Core Organic Chemistry Chapter 16.20: Diels–Alder Reaction Forming Cyclic Products: Stereochemistry
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JoVE Core Organic Chemistry Chapter 16.21: Diels–Alder Reaction Forming Bridged Bicyclic Products: Stereochemistry
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JoVE Core Organic Chemistry Chapter 16.22: Diels–Alder Reaction: Characteristics of Dienes
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JoVE Core Organic Chemistry Chapter 16.23: Diels–Alder Reaction: Characteristics of Dienophiles
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JoVE Core Organic Chemistry Chapter 16.24: Thermal Sigmatropic Reactions: Overview
30
JoVE Core Organic Chemistry Chapter 16.25: [3,3] Sigmatropic Rearrangement of 1,5-Dienes: Cope Rearrangement
30
JoVE Core Organic Chemistry Chapter 16.26: [3,3] Sigmatropic Rearrangement of Allyl Vinyl Ethers: Claisen Rearrangement
30
JoVE Core Organic Chemistry Chapter 16.27: Woodward–Hoffmann Selection Rules and Microscopic Reversibility

Capítulo 0: Aromatic Compounds

30
JoVE Core Organic Chemistry Chapter 17.1: Aromatic Compounds: Overview
30
JoVE Core Organic Chemistry Chapter 17.2: Nomenclature of Aromatic Compounds with a Single Substituent
30
JoVE Core Organic Chemistry Chapter 17.3: Nomenclature of Aromatic Compounds with Multiple Substituents
30
JoVE Core Organic Chemistry Chapter 17.4: Structure of Benzene: Kekulé Model
30
JoVE Core Organic Chemistry Chapter 17.5: Structure of Benzene: Molecular Orbital Model
30
JoVE Core Organic Chemistry Chapter 17.7: Criteria for Aromaticity and the Hückel 4n + 2 Rule
30
JoVE Core Organic Chemistry Chapter 17.8: Hückel's Rule Diagram of π MOs: Frost Circle
30
JoVE Core Organic Chemistry Chapter 17.9: Frost Circles for Different Conjugated Systems
30
JoVE Core Organic Chemistry Chapter 17.13: Aromatic Hydrocarbon Anions: Structural Overview
30
JoVE Core Organic Chemistry Chapter 17.14: Aromatic Hydrocarbon Cations: Structural Overview
30
JoVE Core Organic Chemistry Chapter 17.15: Five-Membered Heterocyclic Aromatic Compounds: Overview
30
JoVE Core Organic Chemistry Chapter 17.19: NMR Spectroscopy of Aromatic Compounds

Capítulo 0: Reactions of Aromatic Compounds

30
JoVE Core Organic Chemistry Chapter 18.4: NMR Spectroscopy of Benzene Derivatives
30
JoVE Core Organic Chemistry Chapter 18.5: Reactions at the Benzylic Position: Oxidation and Reduction
30
JoVE Core Organic Chemistry Chapter 18.7: Reactions at the Benzylic Position: Halogenation
30
JoVE Core Organic Chemistry Chapter 18.8: Electrophilic Aromatic Substitution: Overview
30
JoVE Core Organic Chemistry Chapter 18.9: Electrophilic Aromatic Substitution: Chlorination and Bromination of Benzene
30
JoVE Core Organic Chemistry Chapter 18.10: Electrophilic Aromatic Substitution: Fluorination and Iodination of Benzene
30
JoVE Core Organic Chemistry Chapter 18.11: Electrophilic Aromatic Substitution: Nitration of Benzene
30
JoVE Core Organic Chemistry Chapter 18.12: Electrophilic Aromatic Substitution: Sulfonation of Benzene
30
JoVE Core Organic Chemistry Chapter 18.13: Electrophilic Aromatic Substitution: Friedel–Crafts Alkylation of Benzene
30
JoVE Core Organic Chemistry Chapter 18.14: Electrophilic Aromatic Substitution: Friedel–Crafts Acylation of Benzene
30
JoVE Core Organic Chemistry Chapter 18.15: Limitations of Friedel–Crafts Reactions
30
JoVE Core Organic Chemistry Chapter 18.16: Directing Effect of Substituents: ortho–para-Directing Groups
30
JoVE Core Organic Chemistry Chapter 18.17: Directing Effect of Substituents: meta-Directing Groups
30
JoVE Core Organic Chemistry Chapter 18.18: ortho–para-Directing Activators: –CH3, –OH, –⁠NH2, –OCH3
30
JoVE Core Organic Chemistry Chapter 18.19: ortho–para-Directing Deactivators: Halogens
30
JoVE Core Organic Chemistry Chapter 18.20: meta-Directing Deactivators: –NO2, –CN, –CHO, –⁠CO2R, –COR, –CO2H
30
JoVE Core Organic Chemistry Chapter 18.21: Directing and Steric Effects in Disubstituted Benzene Derivatives
30
JoVE Core Organic Chemistry Chapter 18.23: Nucleophilic Aromatic Substitution: Addition–Elimination (SNAr)
30
JoVE Core Organic Chemistry Chapter 18.24: Nucleophilic Aromatic Substitution: Elimination–Addition
30
JoVE Core Organic Chemistry Chapter 18.25: Nucleophilic Aromatic Substitution of Aryldiazonium Salts: Aromatic SN1
30
JoVE Core Organic Chemistry Chapter 18.26: Reduction of Benzene to Cyclohexane: Catalytic Hydrogenation
30
JoVE Core Organic Chemistry Chapter 18.28: Benzene to 1,4-Cyclohexadiene: Birch Reduction Mechanism
30
JoVE Core Organic Chemistry Chapter 18.29: Hydrolysis of Chlorobenzene to Phenol: Dow Process
30
JoVE Core Organic Chemistry Chapter 18.30: Benzene to Phenol via Cumene: Hock Process
30
JoVE Core Organic Chemistry Chapter 18.32: Oxidation of Phenols to Quinones

Capítulo 0: Amines

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JoVE Core Organic Chemistry Chapter 19.1: Amines: Introduction
30
JoVE Core Organic Chemistry Chapter 19.2: Nomenclature of Primary Amines
30
JoVE Core Organic Chemistry Chapter 19.3: Nomenclature of Secondary and Tertiary Amines
30
JoVE Core Organic Chemistry Chapter 19.4: Nomenclature of Aryl and Heterocyclic Amines
30
JoVE Core Organic Chemistry Chapter 19.5: Structure of Amines
30
JoVE Core Organic Chemistry Chapter 19.6: Physical Properties of Amines
30
JoVE Core Organic Chemistry Chapter 19.7: Basicity of Aliphatic Amines
30
JoVE Core Organic Chemistry Chapter 19.8: Basicity of Aromatic Amines
30
JoVE Core Organic Chemistry Chapter 19.9: Basicity of Heterocyclic Aromatic Amines
30
JoVE Core Organic Chemistry Chapter 19.10: NMR Spectroscopy Of Amines
30
JoVE Core Organic Chemistry Chapter 19.12: Mass Spectrometry of Amines
30
JoVE Core Organic Chemistry Chapter 19.13: Preparation of Amines: Alkylation of Ammonia and Amines
30
JoVE Core Organic Chemistry Chapter 19.14: Preparation of 1° Amines: Azide Synthesis
30
JoVE Core Organic Chemistry Chapter 19.15: Preparation of 1° Amines: Gabriel Synthesis
30
JoVE Core Organic Chemistry Chapter 19.16: Preparation of Amines: Reduction of Oximes and Nitro Compounds
30
JoVE Core Organic Chemistry Chapter 19.17: Preparation of Amines: Reduction of Amides and Nitriles
30
JoVE Core Organic Chemistry Chapter 19.18: Preparation of Amines: Reductive Amination of Aldehydes and Ketones
30
JoVE Core Organic Chemistry Chapter 19.19: Preparation of 1° Amines: Hofmann and Curtius Rearrangement Overview
30
JoVE Core Organic Chemistry Chapter 19.20: Preparation of 1° Amines: Hofmann and Curtius Rearrangement Mechanism
30
JoVE Core Organic Chemistry Chapter 19.21: Amines to Amides: Acylation of Amines
30
JoVE Core Organic Chemistry Chapter 19.22: Amines to Alkenes: Hofmann Elimination
30
JoVE Core Organic Chemistry Chapter 19.24: Amines to Alkenes: Cope Elimination
30
JoVE Core Organic Chemistry Chapter 19.25: 1° Amines to Diazonium or Aryldiazonium Salts: Diazotization with NaNO2 Overview
30
JoVE Core Organic Chemistry Chapter 19.26: 1° Amines to Diazonium or Aryldiazonium Salts: Diazotization with NaNO2 Mechanism
30
JoVE Core Organic Chemistry Chapter 19.27: 2° Amines to N-Nitrosamines: Reaction with NaNO2
30
JoVE Core Organic Chemistry Chapter 19.28: Diazonium Group Substitution with Halogens and Cyanide: Sandmeyer and Schiemann Reactions
30
JoVE Core Organic Chemistry Chapter 19.29: Diazonium Group Substitution: –OH and –H
30
JoVE Core Organic Chemistry Chapter 19.30: Aryldiazonium Salts to Azo Dyes: Diazo Coupling
30
JoVE Core Organic Chemistry Chapter 19.31: Amines to Sulfonamides: The Hinsberg Test

Capítulo 0: Radical Chemistry

30
JoVE Core Organic Chemistry Chapter 20.1: Radicals: Electronic Structure and Geometry
30
JoVE Core Organic Chemistry Chapter 20.4: Electron Paramagnetic Resonance (EPR) Spectroscopy: Organic Radicals
30
JoVE Core Organic Chemistry Chapter 20.5: Radical Formation: Overview
30
JoVE Core Organic Chemistry Chapter 20.6: Radical Formation: Homolysis
30
JoVE Core Organic Chemistry Chapter 20.7: Radical Formation: Abstraction
30
JoVE Core Organic Chemistry Chapter 20.8: Radical Formation: Addition
30
JoVE Core Organic Chemistry Chapter 20.9: Radical Formation: Elimination
30
JoVE Core Organic Chemistry Chapter 20.10: Radical Reactivity: Overview
30
JoVE Core Organic Chemistry Chapter 20.11: Radical Reactivity: Steric Effects
30
JoVE Core Organic Chemistry Chapter 20.12: Radical Reactivity: Concentration Effects
30
JoVE Core Organic Chemistry Chapter 20.13: Radical Reactivity: Electrophilic Radicals
30
JoVE Core Organic Chemistry Chapter 20.14: Radical Reactivity: Nucleophilic Radicals
30
JoVE Core Organic Chemistry Chapter 20.15: Radical Reactivity: Intramolecular vs Intermolecular
30
JoVE Core Organic Chemistry Chapter 20.16: Radical Autoxidation
30
JoVE Core Organic Chemistry Chapter 20.17: Radical Oxidation of Allylic and Benzylic Alcohols
30
JoVE Core Organic Chemistry Chapter 20.18: Radical Substitution: Halogenation of Alkanes and Alkyl Substituents
30
JoVE Core Organic Chemistry Chapter 20.19: Radical Halogenation: Thermodynamics
30
JoVE Core Organic Chemistry Chapter 20.21: Radical Halogenation: Stereochemistry
30
JoVE Core Organic Chemistry Chapter 20.22: Radical Substitution: Allylic Chlorination
30
JoVE Core Organic Chemistry Chapter 20.23: Radical Substitution: Allylic Bromination
30
JoVE Core Organic Chemistry Chapter 20.24: Radical Substitution: Hydrogenolysis of Alkyl Halides with Tributyltin Hydride
30
JoVE Core Organic Chemistry Chapter 20.25: Radical Anti-Markovnikov Addition to Alkenes: Overview
30
JoVE Core Organic Chemistry Chapter 20.26: Radical Anti-Markovnikov Addition to Alkenes: Mechanism
30
JoVE Core Organic Chemistry Chapter 20.27: Radical Anti-Markovnikov Addition to Alkenes: Thermodynamics
30
JoVE Core Organic Chemistry Chapter 20.28: Vicinal Diols via Reductive Coupling of Aldehydes or Ketones: Pinacol Coupling Overview
30
JoVE Core Organic Chemistry Chapter 20.30: Alkenes via Reductive Coupling of Aldehydes or Ketones: McMurry Reaction
30
JoVE Core Organic Chemistry Chapter 20.31: α-Hydroxy Ketones via Reductive Coupling of Esters: Acyloin Condensation Overview

Capítulo 0: Synthetic Polymers

30
JoVE Core Organic Chemistry Chapter 21.2: Characteristics and Nomenclature of Homopolymers
30
JoVE Core Organic Chemistry Chapter 21.3: Characteristics and Nomenclature of Copolymers
30
JoVE Core Organic Chemistry Chapter 21.4: Polymers: Defining Molecular Weight
30
JoVE Core Organic Chemistry Chapter 21.5: Polymers: Molecular Weight Distribution
30
JoVE Core Organic Chemistry Chapter 21.6: Polymer Classification: Architecture
30
JoVE Core Organic Chemistry Chapter 21.7: Polymer Classification: Crystallinity
30
JoVE Core Organic Chemistry Chapter 21.8: Polymer Classification: Stereospecificity
30
JoVE Core Organic Chemistry Chapter 21.10: Radical Chain-Growth Polymerization: Overview
30
JoVE Core Organic Chemistry Chapter 21.11: Radical Chain-Growth Polymerization: Mechanism
30
JoVE Core Organic Chemistry Chapter 21.12: Radical Chain-Growth Polymerization: Chain Branching
30
JoVE Core Organic Chemistry Chapter 21.13: Anionic Chain-Growth Polymerization: Overview
30
JoVE Core Organic Chemistry Chapter 21.14: Anionic Chain-Growth Polymerization: Mechanism
30
JoVE Core Organic Chemistry Chapter 21.16: Cationic Chain-Growth Polymerization: Mechanism
30
JoVE Core Organic Chemistry Chapter 21.17: Ziegler–Natta Chain-Growth Polymerization: Overview
30
JoVE Core Organic Chemistry Chapter 21.19: Step-Growth Polymerization: Overview
30
JoVE Core Organic Chemistry Chapter 21.20: Molecular Weight of Step-Growth Polymers
30
JoVE Core Organic Chemistry Chapter 21.22: Types of Step-Growth Polymers: Polyesters
30
JoVE Core Organic Chemistry Chapter 21.24: Olefin Metathesis Polymerization: Overview
30
JoVE Core Organic Chemistry Chapter 21.25: Olefin Metathesis Polymerization: Ring-Opening Metathesis Polymerization (ROMP)
30
JoVE Core Organic Chemistry Chapter 21.26: Olefin Metathesis Polymerization: Acyclic Diene Metathesis (ADMET)

TABLA DE CONTENIDOS

JoVE Core
Organic Chemistry

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Prepararación de alquinos: Deshidrohalogenación

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JoVE Core Organic Chemistry Chapter 9.5: Prepararación de alquinos: Deshidrohalogenación

Introduction

Alkynes can be prepared by dehydrohalogenation of vicinal or geminal dihalides in the presence of a strong base like sodium amide in liquid ammonia. The reaction proceeds with the loss of two equivalents of hydrogen halide (HX) via two successive E2 elimination reactions.

Reaction Mechanism – E2 pathway

Vicinal dihalides

In the first elimination step, the strong base abstracts the proton from the dihalide that is oriented anti to the leaving group. Since E2 reactions follow a concerted pathway, the abstraction of a proton and departure of the halide leaving group occur simultaneously to form a haloalkene.

In the second elimination reaction, another equivalent of the strong base reacts with the haloalkene in a similar fashion to give the desired alkyne.

Geminal dihalides

Likewise, geminal dihalides, when treated with two equivalents of a sodium amide, undergo double dehydrohalogenation to give alkynes.

Terminal dihalides

Dehydrohalogenation of terminal dihalides yields terminal alkynes as the final product. In the presence of a strong base like sodium amide, terminal alkynes get converted to acetylide ions. In such cases, a third equivalent of the base is required to complete the dehydrohalogenation of the remaining haloalkene.

Protonation of the acetylide ions with water or an aqueous acid completes the reaction.

Application in Organic Synthesis

Dehydrohalogenation of vicinal dihalides is a useful intermediate step in the conversion of alkenes to alkynes. For example, chlorination of 1-propene gives 1,2-dichloropropane – a vicinal dihalide, which upon double dehydrohalogenation yields 1-propyne.

Similarly, alkynes can also be synthesized from ketones via dehydrohalogenation of geminal dihalides. For example, treatment of acetone with phosphorous pentachloride yields 2,2-dichloropropane – a geminal dihalide, which undergoes double dehydrohalogenation to give 1-propyne.

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