alcholes y fenoles2
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Documento informativoTRANSCRIPT
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Alcoholes y fenolesAlcoholes y fenoles
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OH
O
HO
OH
HO OH
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Alcoholes/fenoles/Alcoholes/fenoles/enolesenoles
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ColesterolColesterol Vitamina D3 Vitamina D3 ((ColecalciferolColecalciferol))
OH
OH
HO
O
GeraniolGeraniol ConiferolConiferol
Alcoholes de origen naturalAlcoholes de origen natural
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Los alcoholes se nombran siguiendo las normas estándar de la IUPAC
• Seleccione la cadena más larga de átomos de C que contienen el grupo OH;
• Eliminar la o y agregar ol después del nombre básico
• Numere la cadena partiendo del extremo más cercano al grupo OH
• El número es localizado después de -an y antes de –ol, por ejemplobutan-2-ol
• posiciones de los sustituyentes en la cadena lateral se basan en el número asignado al grupo OH
NomenclaturaNomenclatura de de alcoholesalcoholes
OHOH
OHHOHO OH
OH
OH
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NomenclaturaNomenclatura de de alcoholesalcoholes
OH
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FERMENTACIÓN
azúcares + levadura alcohol etílico + CO2
Zumo de uvas => vino
Cebada => cerveza
Arroz => sake
Caña de azucar => aguardiente..
~5-11% ethanol
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=>
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Domasevitch, K.V. Acta Cryst. (2013). C69, 175–178
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2-(1,4,7,10- tetrazaciclododecan-1-yl)cyclohexan-1-ol (cycyclen)
de Sousa, AS.; Sannasy, D.; FernandesM.A.; Marques, H.M. Acta Cryst. (2012). C68, o383–o386
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Kerscher, T.; Betz, ,R.; Klufers, P.; Mayer, P. Acta Cryst. (2009). E65, o211
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Fun, H.-K.; Chantrapromma, S.; Charoen Pakhathirathien, C.; Karalai, C.; Chantrapromma, K. Acta Cryst. (2012). E68, o520–o521
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SolubilidadSolubilidad en aguaen agua
Solubility decreases as the size of the alkyl group increases.
=>
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Fileti, E.E.; Chaudhuri, P.; Canuto, S. Chemical Physics Letters 400 (2004) 494–499
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Thode AB, Kruse SW, Nix JC, Jones DNM. J. Mol. Biol. 2008;376(5):1360-1376.
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http://www.mhhe.com/physsci/chemistry/carey/student/olc/ch24phenols.html
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Hidruro de sodio remueve el protón para dar un alcoxido, la base conjugada del alcohol
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AcidezAcidez de de alcoholesalcoholes
•• ppKKaa 15.515.5--18.0 (agua: 15.7)18.0 (agua: 15.7)•• Acidez decrece con el tamaAcidez decrece con el tamañño de la o de la
cadena alifcadena alifááticatica•• Los grupos Los grupos electroatractoreselectroatractores aumentan aumentan
la acidezla acidez•• Los fenoles tienen Los fenoles tienen ppKKaa 8.08.0--9.09.0
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•• GrupoGrupo hidroxilohidroxilo unidounido a un a un anilloanilloaromaromááticotico
FenolesFenoles
OH OH
OH
H2N
FenolFenol DopaminaDopaminaO
OH
NH
O
O
OH
CapsaicinaCapsaicina TetrahidrocanabinolTetrahidrocanabinol(THC)(THC)
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IsoproterenolIsoproterenol o o isoprenalinaisoprenalina
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Nomenclatura de fenolesNomenclatura de fenoles
•• El carbono al cuEl carbono al cuáál estl estáá unido el grupo unido el grupo --OH se OH se asume como el carbono 1asume como el carbono 1
•• Para fenoles Para fenoles disustituidosdisustituidos, usando nombres , usando nombres comunes use comunes use orthoortho--; ; metameta-- y y parapara--
•• Nombres comunes Nombres comunes cresolescresoles, , xilenolesxilenoles
OH
Cl
m-clorofenol
OH
H3C
p-cresol
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PhOH + EtO- PhO- + EtOH
pKa = 9.95
H2O + PhOH H3O+ + PhO-
Ka = [H3O+][PhO-]/[PhOH] = 10-9.95
H2O + EtOH H3O+ + EtO-
Ka = [H3O+][EtO-]/[EtOH] = 10-18
pKa = 18
Base fuerte Base débil
K = 10-9.95 / 10-18 = 108.0
OH OH
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HIDRATACIÓN REGIOESPECÍFICA DE ALQUENOS
Hidroboración/oxidación: syn, anti-Markovnikov
Oximercuración/reducción: Markovnikov
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=>
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9-borabiciclo[3.3.1]nonane
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monoisopinocamfeilborane (IpcBH2),
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Reducción de compuestos carbonilo
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Adición de Organometálicos a grupos carbonilo
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O
R Mg
O
R Mgδ+δ−
Mg
OR
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Esquilibrio Schlenk
Reactivo de Grignard en
solución
Mecanismo polar
Mecanismo transferenciaelectrónica
+ RH
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Formación del reactivo de Grignard
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Garst, J.F.; Swift, B.L. J. Am. Chem. Soc., 1989, 111, 241–250