Químicadelos compuestos( carbonílicos((depa.fquim.unam.mx/amyd//archivero/ALDEHIDOSYCETONAS2...•...
Transcript of Químicadelos compuestos( carbonílicos((depa.fquim.unam.mx/amyd//archivero/ALDEHIDOSYCETONAS2...•...
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Química de los compuestos carbonílicos
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el grupo carbonilo
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Compounds that have only carbon and hydrogen atoms bonded to the carbonyl group
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Compounds that contain an electronegative atom bonded to the carbonyl group
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The presence or absence of a leaving group on the carbonyl carbon determines the type of reactions these compounds undergo.
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el grupo carbonilo
Electrostatic potential map of formaldehyde, H2C=O
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Ejemplos de aldehídos y cetonas
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Pungent compounds found in capsicum, black pepper, and ginger
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Aroma y sabor. Reacciones involucradas.
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Generación de aromas y sabores via reacción de Maillard
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Nomenclatura de aldehídos
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Nomenclatura de cetonas
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¿como se preparan los aldehídos y las cetonas?
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REACCIONES DE ALDEHIDOS Y CETONAS
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ReacFvidad del grupo carbonilo
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Reac2vidades rela2vas de aldehídos y cetonas
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Efectos electrónicos
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efectos estéricos
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trayectoria de Bürgi-‐Dunitz
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LUMO
HOMO
HOMO highest occupied molecular orbital LUMO lowest unoccupied molecular orbital
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HOMO
LUMO
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Adición nucleoRlica bajo condiciones básicas
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Adición nucleoRlica bajo condiciones ácidas
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Nucleófilos
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Nucleófilos de oxígeno
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Hidratación catalizada por base
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Hidratación catalizada por ácido
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Formación de acetales
Catalizadores mas comunes
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Mecanismo de la formación de acetales
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Posición del equilibrio
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Estabilidad de los acetales
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• Carbonyls can be aYacked by alcohols to form hemiacetals.
– The intramolecular reacFon is generally favored for 5 and 6-‐ membered rings. WHY?
Cyclic Structures of Monosaccharides
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• Monosaccharides, like glucose, can also undergo ring-‐closing hemiacetal formaFon.
• The equilibrium greatly favors the closed form called pyranose.
Cyclic Structures of Monosaccharides
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Anomeric effect
• Which would you predict to be more stable?
9
– Beta 67% , alpha 33%, open 0.01%
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• Ketoses form both furanose (5-‐membered) and pyranose (6-‐membered) rings:
Cyclic Structures of Monosaccharides
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Cyclic Structures of Monosaccharides
• The equilibrium concentrations in water are above.
70% β 0.7% 23%-β 2% α 5%-α
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¿de donde provienen los términos furanosa y piranosa?
O Opirano furano
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• The furanose form takes part in most biochemical reacFons.
Cyclic Structures of Monosaccharides
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• Disaccharides form when two sugars connect through a glycosidic linkage.
– The 1 à 4 glycosidic linkage is most common.
– The bottom ring is capable of mutarotaFon at its anomeric posiFon.
– Because the anomeric posiFon of the bottom ring is a HEMIACETAL rather than an acetal, it is in equilibrium with the open form. Thus, maltose is a reducing sugar.
Disaccharides
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• Cellobiose is similar to maltose. WHAT are the differences?
• Will cellobiose be a reducing sugar?
Disaccharides
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• Sucrose (table sugar) is also a disaccharide.
– Honey bees can convert sucrose into a mixture of sucrose, fructose, and glucose.
– Fructose is very sweet. • Sucrose is not a reducing sugar. WHY?
Disaccharides
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• Cellulose is a polysaccharide containing 7000–12000 glucose units connected through glycosidic bonds.
• How is cellulose capable of giving plants like trees their rigidity and strength?
Polysaccharides
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• Starch is a major components of grains and other foods, like potatoes. What is the difference between molecules of starch and molecules of cellulose? Starch is made of amylose and amylopecFn.
•
Polysaccharides
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• Amylopectin has some 1à6-‐ α-‐glycoside branches.
Polysaccharides
We can eat corn and potatoes, but not grass or trees. WHY?
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• Lactose is another disaccharide.
• Some people have trouble digesFng lactose.
Disaccharides
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Nucleófilos de nitrógeno
Aminas primarias
imina
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Mecanismo de la formación de iminas
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Rapidez de formación de iminas en función del pH
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Aminas secundarias
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