grupos funcionales y prioridad by lm0N43u

VIEWS: 93 PAGES: 28

									Functional Groups
– Alkenes
  • Ethene (ethylene) is a major industrial feedstock
     – Used in the production of ethanol, ethylene oxide and the
       polymer polyethylene




  • Propene (propylene) is also very important in industry
     – Molecular formula C3H6
     – Used to make the polymer polypropylene and is the starting
       material for acetone
  • Many alkenes occur naturally


                                                                    2
– Alkynes
  • Ethyne (acetylene) is used in welding torches
    because it burns at high temperature

  • Many alkynes are of biological interest
     – Capillin is an antifungal agent found naturally
     – Dactylyne is a marine natural product
     – Ethinyl estradiol is a synthetic estrogen used in oral
       contraceptives
– Benzene: A Representative Hydrocarbon
   • Benzene is the prototypical aromatic compound
       – The Kekulé structure (named after August Kekulé who formulated it)
           is a six-membered ring with alternating double and single bonds




   • Benzene does not actually have discreet single and double
     carbon-carbon bonds
       – All carbon-carbon bonds are exactly equal in length (1.38 Å)
       – This is between the length of a carbon-carbon single bond and a
         carbon-carbon double bond
   • Resonance theory explains this by suggesting there are two
     resonance hybrids that contribute equally to the real structure
       – The real structure is often depicted as a hexagon with a circle in the
         middle
  Some Well-known Aromatic Compounds

 CO 2H O
        OCCH3

        acetyl salicylic acid
                                                   ibuprofin
                                    HO2C
HO 2C              CH3
               N                               O
                                         CH2CNH                S
                                                           N
                                CH3
                     NH                        penicillin G CO H
                                N                             2
   lysergic acid


                                         OH
                                O
                                    morphine
                      OH
- Alkyl Halides
 In alkyl halides, a halogen (F, Cl, Br, I)
 replaces the hydrogen of an alkane
– Alcohols
   • In alcohols the hydrogen of the alkane is replaced
     by the hydroxyl (-OH) group
      – An alcohol can be viewed as either a hydroxyl derivative
        of an alkane or an alkyl derivative of water




   • Alcohols are also classified according to the carbon
     the hydroxyl is directly attached to




                            Chapter 2
                       Some Alcohols

                           OH                 OH
CH3CH2OH     HO            CHCH2NH2           CHCHNHCH3
                                                CH3
  ethanol         HO   adrenaline       pseudephidrine

      OH
HOCH2CHCH 2OH
  glycerol                             cholesterol


                  HO
Alcohols are Found in Many Natural Products

        HO



          O                N CH3

                       H
        HO
               Morphine
     most abundant of opium's alk aloids
           CH3                         CH3
           N                           N     Designer Drugs


                  OH                          OH
          O                           O
   OH                         OCH3
    morphine                     codeine
          CH3                          CH3
          N                            N




                  O                           OAc
          O                           O
   OCH3                       OAc
      oxycodone                     heroin
  oxycontin (slow release)
percocet (w/ acetominophen)
– Ethers
   • Ethers have the general formula R-O-R or R-O-R’
     where R’ is different from R
      – These can be considered organic derivatives of water in
        which both hydrogens are replaced by organic groups
      – The bond angle at oxygen is close to the tetrahedral
        angle
– Amines
  • Amines are organic derivatives of ammonia
     – They are classified according to how many alkyl groups
       replace the hydrogens of ammonia
     – This is a different classification scheme than that used in
       alcohols
– Aldehydes and Ketones
   • Both contain the carbonyl group


   • Aldehydes have one carbon attached to the carbonyl group




   • Ketones have two organic groups attached to the carbonyl
     group


   • The carbonyl carbon is sp2 hybridized
       – It is trigonal planar and has bond angle about 120o
             Adrogenic/Anabolic Steroids


                  CH3 OH                           CH3 O

      CH3     H                      CH3       H

         H        H                        H       H
O                            O
    Testosterone                  Androstenedione
– Carboxylic Acids, Esters and Amides
   • All these groups contain a carbonyl group bonded
     to an oxygen or nitrogen
   • Carboxylic Acids
       – Contain the carboxyl (carbonyl + hydroxyl) group




   • Esters
       – A carbonyl group is bonded to an alkoxyl (OR’) group
                   Analgesics

     CO2H O
         OCCH3

                                    (S)(+)-
acetyl salicylic acid              ibuprofin
                            HO2C
      Fats and Fatty Acids

                                           CO2H
                  palmitic acid (a fatty acid)
         O
CH2    OCR
        O
CH     OCR
        O
CH2     OCR      R = n-C15H31
a triglyceride
     From Ergot Fungus

         HO 2C        CH3
                    N
                      H


(+) lysergic acid
                         NH
            Functional Groups
                     link to Carey’s site



(CH3)2N
                                                  O        O
                        OH
                                            H2NCHCNHCHCOCH 3
                           C CH
                                            HOCCH 2      CH2

                                              O
     O
          Mifepristone (RU-486)              Aspartame
   • Amide
       – A carbonyl group is bonded to a nitrogen derived from
         ammonia or an amine




– Nitriles
   • An alkyl group is attached to a carbon triply bonded
     to a nitrogen
       – This functional group is called a cyano group




                           Chapter 2
Summary of Important Families of Organic
             Compounds
Summary (cont.)
    From the Bark of the
      Pacific Yew Tree
                  O

                      O      O       OH


O    NH   O
                                          O
              O
                          OH O O
       OH
                                 O
                             O

          Taxus brevifolia
              Prioridad de grupos funcionales
Grupo funcional       Nombre como sufijo         Nombre como prefijo
ácido carboxílico     ácido -oico                carboxi
                      ácido –carboxílico
ácido sulfónico       ácido –sulfónico           sulfo
anhídrido             anhídrido -oico
                      anhídrido –carboxílico
éster                 -oato de                   alcoxicarbonil
                      -carboxilato de
halogenuro de acilo   halogenuro de -oilo        halocarbonil
                      halogenuro de –carbonilo
amida                 -amida                     amido
                      -carboxamida
nitrilo               -nitrilo                   ciano
                      -carbonitrilo
aldehído              -al                        oxo
                      -carbaldehído
cetona                -ona                       oxo
             Prioridad de grupos funcionales

Grupo funcional      Nombre como sufijo   Nombre como prefijo
alcohol              -ol                  hidroxi
fenol                -ol                  hidroxi
tiol                 -tiol                mercapto
amina                -amina               amino
imina                -imina               imino
alqueno              -eno                 alquenil
alquino              -ino                 alquinil
alcano               -ano                 alquil
ORDEN DE PRIORIDAD
1.- Ácidos carboxílicos
2.- Derivados de ácidos (anhídridos > ésteres > haluros de acilo > amidas > nitrilos)
3.- Aldehídos > cetonas
4.- Alcoholes > fenoles
5.- Aminas
6.- Éteres
7.-Halogenuros de alquilo
8.- Alquenos > alquinos
La función principal determina:
•el nombre del compuesto
•la cadena carbonada principal, que debe ser la más larga posible que contenga la función
principal
•los números localizadores de los sustituyentes y funciones secundarias
                                                            Ejemplos
     Clase          Principal (P)   Secundaria (S)
    alcanos             -ano             -il-              (P) metano
                                                     (S) 2-metilpropano
   alquenos             -eno            -enil-              (P) eteno
                                                      (S) etenilbenceno
  aromáticos          Benceno            -il-             (P) benceno
                                                         (S) feniletano
    alquinos            -ino            -inil-              (P) etino
                                                       (S) etinilbenceno
   haluros de       fluoruro de,     fluor, cloro,    (P)cloruro de etilo
                                                     (S) 2-cloropropano
    alquilo          cloruro de,     bromo, iodo
                    bromuro de,
                      ioduro de
     éteres              éter           -oxi-,          (P) dietil éter
                                                     (S) metoxibenceno
aminas primarias      -amina           -amino-          (P) etilamina
                                                     (S) 2-aminoetanol
    aminas            -amina         alquilamino       (P) dietilamina
                                                             (S) 2-
  secundarias
                                                      metilaminoetanol
aminas terciarias     -amina        dialquilamino-     (P) trietilamina
                                                             (S) 2-
                                                      dietilaminoetanol
                                                                      Ejemplos
     Clase           Principal (P)     Secundaria (S)
alcoholes, fenoles        -ol             -hidroxi-               (P) etanol
                                                           (S) 4-hidroxipentanal
     cetonas              -ona              -oxo-               (P) propanona
                                                             (P) dimetilacetona
                         cetona                           (S) ácido 3-oxobutanoico
    aldehídos              -al            -formil-                (P) etanal
                                                              (P) etanaldehído
                        aldehído                                 (S) ácido 4-
                                                               formilbenzoico
     nitrilo             -nitrilo          -ciano-              (P) etanonitrilo
                                                           (S) 2-cianociclohexanol
     amidas              -amida         -carbamoil-              (P) etanamida
                                                                  (S) ácido 3-
                                                             carbamoilbutanoico
 haluros de acilo    haluro de -oílo    -haloformil-        (P) cloruro de bezoílo
                                                                  (S) ácido 4-
                                                          haloformilciclohexanosulf
                                                                     ónico
     ésteres           -ato de -ilo    -alcoxicarbonil-      (P) acetato de etilo o
                                                               etanoato de etilo
                                                                   (S) ácido
                                                            etoxicarbonilacético
                                                                  (P) ácido etanoico
     ácidos           ácido... -oico      -carboxi-         ácido 3-carboxipentanodioico

  carboxílicos

								
To top