QUÍMICA ORGANICA     ¿Qué es la química orgánica?   ¿Por qué la han estudiado tantas personas?   ¿Por qué debes estudiarla...
 
 
 
QUÍMICA ORGÁNICA  estudio de los compuestos de carbono
Nomenclatura IUPAC de  Alcanos   NO   Ramificados
<ul><li>Recordar: </li></ul><ul><ul><li>metano CH 4 </li></ul></ul><ul><ul><li>etano CH 3 CH 3 </li></ul></ul><ul><ul><li>...
Nombres IUPAC de Alcanos No Ramificados <ul><li>Nota: el prefijo  n  no es parte del nombre IUPAC de ningún alcano. </li><...
<ul><li># de carbonos  Nombre Estructura </li></ul><ul><li>5 pentano CH 3 (CH 2 ) 3 CH 3 </li></ul><ul><li>6 hexano CH 3 (...
<ul><li># de carbonos  Nombre Estructura </li></ul><ul><li>11 undecano CH 3 (CH 2 ) 9 CH 3 </li></ul><ul><li>12 dodecano C...
<ul><li># de carbonos  Nombre Estructura </li></ul><ul><li>17 heptadecano CH 3 (CH 2 ) 15 CH 3 </li></ul><ul><li>18 octade...
Aplicación de las Reglas  de la IUPAC: Los Nombres de los Isómeros C 6 H 14
Los Isómeros C 6 H 14 CH 3 CH 2 CH 2 CH 2 CH 2 CH 3 (CH 3 ) 2 CHCH 2 CH 2 CH 3 (CH 3 CH 2 ) 2 CHCH 3 (CH 3 ) 2 CHCH(CH 3 )...
<ul><li>El nombre IUPAC del alcano no ramificado con una cadena de 6 carbonos es hexano. </li></ul>Los Isómeros C 6 H 14 C...
Nomenclatura IUPAC de Alcanos  Ramificados  1) Selecciona la cadena de carbonos continua más larga y usar el nombre IUPAC ...
Los Isómeros C 6 H 14 (CH 3 ) 2 CHCH 2 CH 2 CH 3 (CH 3 CH 2 ) 2 CHCH 3 2-Metilpentano 3-Metilpentano
<ul><li>Usa prefijos multiplicadores (di-, tri-, tetra-, etc.)  de acuerdo al número de sustituyentes idénticos unidos a l...
Grupos Alquilo
Grupos Metilo y Etilo Metilo Etilo o o C C H H H H H CH 3 CH 2 C H H H CH 3
Grupos Alquilo no Ramificados Si el punto de unión está en un extremo de la cadena, en la nomenclatura IUPAC, se nombra re...
Grupos Alquilo no Ramificados Butilo o Si el punto de unión está en un extremo de la cadena, en la nomenclatura IUPAC, se ...
Grupos Alquilo no Ramificados Hexilo Heptilo Octadecilo CH 3 (CH 2 ) 4 CH 2 CH 3 (CH 2 ) 5 CH 2 CH 3 (CH 2 ) 16 CH 2
Los  Grupos Alquilo C 3 H 7 CH 3 CH 2 CH 2 C C H H H H H C H H o y CH 3 CHCH 3 C C H H H H H C H H o
<ul><li>Nombre IUPAC:  Propilo </li></ul><ul><li>Nombre común :  n -Propilo </li></ul>Los  Grupos Alquilo C 3 H 7 CH 3 CH ...
Nombrando a los Grupos Alquilo  1: Identifica la cadena contínua más larga comenzando en el punto de unión. 2: Drop - ane ...
<ul><li>Nombre IUPAC :  1-Metiletilo </li></ul><ul><li>Nombre común :  Isopropilo </li></ul>Los  Grupos Alquilo C 3 H 7 CH...
<ul><li>Classification:  Primary alkyl group </li></ul><ul><li>Alkyl groups are classified according to the degree of subs...
<ul><li>Classification:  Secondary alkyl group </li></ul><ul><li>Alkyl groups are classified according to the degree of su...
<ul><li>IUPAC name:  Butyl </li></ul><ul><li>Common name:  n -Butyl </li></ul><ul><li>Classification:  Primary alkyl group...
<ul><li>IUPAC name:  1-Methylpropyl </li></ul><ul><li>Common name:  sec -Butyl </li></ul><ul><li>Classification:  Secondar...
<ul><li>IUPAC name:  2-Methylpropyl </li></ul><ul><li>Common name:  Isobutyl </li></ul><ul><li>Classification:  Primary al...
<ul><li>IUPAC name:  1,1-Dimethylethyl </li></ul><ul><li>Common name:  tert -Butyl </li></ul><ul><li>Classification:  Tert...
Nombres IUPAC de Alcanos Altamente Ramificados
Branched alkanes <ul><li>Octane </li></ul>
<ul><li>4-Ethyloctane </li></ul>Branched alkanes
<ul><li>4-Ethyl-3-methyloctane </li></ul>Branched alkanes List substituents in alphabetical order.
<ul><li>4-Ethyl-3,5-dimethyloctane </li></ul>Branched alkanes List substituents in alphabetical order. But don't alphabeti...
First Point of Difference Rule <ul><li>The chain is numbered in the direction that gives the lower locant to the substitue...
First Point of Difference Rule <ul><li>The chain is numbered in the direction that gives the lower locant to the substitue...
Nomenclatura de  Cicloalcanos C n H 2 n
Cycloalkanes <ul><li>Cycloalkanes are alkanes that contain a ring of three or more carbons. </li></ul><ul><li>Count the nu...
Cycloalkanes <ul><li>Name any alkyl groups on the ring in the usual way. </li></ul>Ethylcyclopentane CH 2 CH 3
<ul><li>Name any alkyl groups on the ring in the usual way. </li></ul><ul><li>List substituents in alphabetical order and ...
Nomenclatura de Alquenos
Alkenes <ul><li>Alkenes are hydrocarbons that contain a  carbon-carbon double bond </li></ul><ul><li>also called &quot;ole...
Alkene Nomenclature Ethene or Ethylene (both are acceptable IUPAC names) Propene (Propylene is sometimes used  but is not ...
<ul><li>1)  Find the longest continuous chain that  includes the double bond. </li></ul><ul><li>2)  Replace the - ane  end...
<ul><li>4)  If a substituent is present, identify its position by number.  The double bond takes precedence over alkyl gro...
<ul><li>4)  If a substituent is present, identify its position by number.  Hydroxyl groups take precedence over the double...
<ul><li>methylene </li></ul><ul><li>vinyl </li></ul><ul><li>allyl </li></ul><ul><li>isopropenyl </li></ul>Alkenyl Groups C...
Cycloalkene Nomenclature <ul><li>1)  Replace the - ane  ending of the cycloalkane having the same number of carbons by - e...
<ul><li>1)  Replace the - ane  ending of the cycloalkane having the same number of carbons by - ene . </li></ul><ul><li>2)...
Alquinos
Nomenclature
Nomenclature Higher alkynes are named in much the same way as alkenes except using an - yne  suffix instead of - ene . HC ...
Functional Groups
<ul><li>a structural unit in a molecule responsible for its characteristic behavior under a particular set of reaction con...
<ul><li>Alcohol ROH </li></ul><ul><li>Alkyl halide R X  ( X  = F, Cl, Br, I) </li></ul><ul><li>Amine primary amine:  R NH ...
<ul><li>Ether R O R' </li></ul><ul><li>Nitrile R CN </li></ul><ul><li>Nitroalkane R NO 2 </li></ul><ul><li>Sulfide RSR' </...
Many classes of organic compounds contain a carbonyl group Carbonyl group Acyl group R O C O C
Many classes of organic compounds contain a carbonyl group Carbonyl group Aldehyde R H O C O C
Many classes of organic compounds contain a carbonyl group Carbonyl group Ketone R R' O C O C
Many classes of organic compounds contain a carbonyl group Carbonyl group Carboxylic acid R OH O C O C
Many classes of organic compounds contain a carbonyl group Carbonyl group Ester R OR' O C O C
Many classes of organic compounds contain a carbonyl group Carbonyl group Amide R NH 2 O C O C
IUPAC Nomenclature of Alkyl Halides
<ul><li>The two that are most widely used are: functional class nomenclature substitutive nomenclature </li></ul><ul><li>B...
<ul><li>Name the alkyl group and the halogen as separate words ( alkyl  +  halide ) </li></ul>Functional Class Nomenclatur...
<ul><li>Name the alkyl group and the halogen as separate words ( alkyl  +  halide ) </li></ul>Functional Class Nomenclatur...
<ul><li>Name as halo-substituted alkanes. </li></ul><ul><li>Number the longest chain containing the halogen in the directi...
<ul><li>Name as halo-substituted alkanes. </li></ul><ul><li>Number the longest chain containing the halogen in the directi...
Substitutive Nomenclature of Alkyl Halides <ul><li>Halogen and alkyl groups are of equal rank when  it comes to numbering ...
Substitutive Nomenclature of Alkyl Halides 5-Chloro-2-methylheptane 2-Chloro-5-methylheptane CH 3 Cl Cl CH 3
IUPAC Nomenclature of Alcohols
<ul><li>Name the alkyl group and add &quot;alcohol&quot; as a separate word. </li></ul>Functional Class Nomenclature of Al...
<ul><li>Name the alkyl group and add &quot;alcohol&quot; as a separate word. </li></ul>Functional Class Nomenclature of Al...
<ul><li>Name as &quot;alkanols.&quot;  Replace -e ending of alkane name by -ol. </li></ul><ul><li>Number chain in directio...
<ul><li>Name as &quot;alkanols.&quot;  Replace -e ending of alkane name by -ol. </li></ul><ul><li>Number chain in directio...
Substitutive Nomenclature of Alcohols <ul><li>Hydroxyl groups outrank  alkyl groups when  it comes to numbering the chain....
Substitutive Nomenclature of Alcohols 6-Methyl-3-heptanol 5-Methyl-2-heptanol OH CH 3 CH 3 OH
Classes of Alcohols and Alkyl Halides
<ul><li>Alcohols and alkyl halides are classified as primary secondary tertiary according to their &quot;degree of substit...
Classification CH 3 CH 2 CH 2 CH 2 C H 2 F primary alkyl halide secondary alkyl halide tertiary alcohol H OH secondary alc...
Ethers, Epoxides, and Sulfides
Nomenclature of Ethers, Epoxides, and Sulfides
<ul><li>name as alkoxy derivatives of alkanes </li></ul>Substitutive IUPAC Names of Ethers CH 3 O CH 2  CH 3 methoxy ethan...
<ul><li>name the groups attached to oxygen in  alphabetical order as separate words;  &quot;ether&quot; is  last word </li...
<ul><li>name as alkylthio derivatives of alkanes </li></ul>Substitutive IUPAC Names of Sulfides CH 3 S CH 2  CH 3 methylth...
<ul><li>analogous to ethers, but replace “ether” as last word in the name by “sulfide.” </li></ul>Functional Class IUPAC N...
Names of Cyclic Ethers O O O O O O Oxirane (Ethylene oxide) Oxetane Oxolane (tetrahydrofuran) Oxane (tetrahydropyran) 1,4-...
Names of Cyclic Sulfides S S S S Thiirane Thietane Thiolane Thiane
Amines
Amine Nomenclature
<ul><li>Alkylamine </li></ul><ul><ul><li>N attached to alkyl group </li></ul></ul><ul><li>Arylamine </li></ul><ul><ul><li>...
<ul><li>Two IUPAC styles </li></ul><ul><li>1) analogous to alcohols:  replace - e  ending by - anamine </li></ul><ul><li>2...
Examples:  some primary alkylamines (RNH 2 :  one carbon directly attached to N) CH 3 CH 2 N H 2 ethylamine  or  ethanamin...
<ul><li>Name as derivatives of aniline. </li></ul>Nomenclature of Primary Arylamines (ArNH 2 ) p -fluoroaniline 5-bromo-2-...
Amino groups as substituents <ul><li>amino groups rank below OH groups and higher oxidation states of carbon </li></ul><ul...
<ul><li>Name as  N -substituted derivatives of parent  primary amine. </li></ul><ul><li>(N is a locant-it is not alphabeti...
Examples CH 3 N HCH 2 CH 3 N -methylethylamine 4-chloro- N -ethyl-3-nitroaniline N , N -dimethylcycloheptylamine N HCH 2 C...
<ul><li>A nitrogen with four substituents is positively charged and is named as a derivative of  ammonium  ion (NH 4 + ). ...
<ul><li>When all four atoms attached to N are carbon, the ion is called a  quaternary ammonium  ion and salts that contain...
Nomenclature
IUPAC Nomenclature of Aldehydes Base the name on the chain that contains the carbonyl group and replace the  -e  ending of...
IUPAC Nomenclature of Aldehydes 4,4-dimethylpent an al 5-hex en al 2-phenylprop ane dial (keep the  -e  ending before  -di...
IUPAC Nomenclature of Aldehydes  when named as  a substituent formyl group carbaldehyde or carboxaldehyde when named  as a...
Substitutive IUPAC Nomenclature of Ketones Base the name on the chain that contains the carbonyl group and replace  -e  by...
Substitutive IUPAC Nomenclature of Ketones 3- hexan one 4-methyl -2- pentan one 4-methylcyclohexan one CH 3 CH 2 CCH 2 CH ...
Functional Class IUPAC Nomenclature of Ketones List the groups attached to the carbonyl separately in alphabetical order, ...
Functional Class IUPAC Nomenclature of Ketones ethyl   propyl  ketone benzyl   ethyl  ketone divinyl ketone CH 3 CH 2 C CH...
Carboxylic Acids
Carboxylic Acid Nomenclature
<ul><ul><li>systematic IUPAC names replace &quot;-e&quot; ending of alkane with &quot;oic acid&quot; </li></ul></ul>System...
<ul><ul><li>common names are based on natural origin rather than structure </li></ul></ul>Systematic Name Common Name meth...
Systematic Name Common Name 2-hydroxypropanoic acid lactic acid ( Z )-9-octadecenoic acid oleic acid O CH 3 CHCOH OH O (CH...
Nomenclature of Carboxylic Acid Derivatives
Acyl Halides <ul><li>name the acyl group and add the word  chloride ,  fluoride ,  bromide , or  iodide  as appropriate </...
Acyl Halides acetyl  chloride 3-butenoyl  chloride p -fluorobenzoyl  bromide   CH 3 C Cl O O H 2 C CHCH 2 C Cl O C Br F
Acid Anhydrides <ul><li>when both acyl groups are the same, name the acid and add the word  anhydride </li></ul><ul><li>wh...
Acid Anhydrides acetic anhydride benzoic anhydride benzoic   heptanoic  anhydride CH 3 C O CCH 3 O O C 6 H 5 C O CC 6 H 5 ...
Esters <ul><li>name as  alkyl   alkanoates </li></ul><ul><li>cite the alkyl group attached to oxygen first (R') </li></ul>...
Esters ethyl  acetate methyl  propanoate 2-chloroethyl  benzoate  CH 3 C O CH 2 CH 3 O O CH 3 CH 2 C O CH 3 C O CH 2 CH 2 ...
Amides having an NH 2  group <ul><li>identify the corresponding carboxylic acid </li></ul><ul><li>replace the  -ic acid  o...
Amides having an NH 2  group acet amide 3-methylbutan amide benz amide CH 3 C N H 2 O O (CH 3 ) 2 CHCH 2 C N H 2 C N H 2 O
Amides having substituents on N <ul><li>name the amide as before </li></ul><ul><li>precede the name of the amide with the ...
Amides having substituents on N N - methyl acetamide N - isopropyl - N - methyl butanamide N , N - diethyl benzamide CH 3 ...
Nitriles <ul><li>add the suffix  -nitrile  to the name of the parent hydrocarbon chain (including the triply bonded carbon...
Nitriles ethanenitrile or:  acetonitrile or:  methyl cyanide benzonitrile 2-methylpropanenitrile or:  isopropyl cyanide CH...
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Nomenclatura

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  • Nomenclatura

    1. 1. QUÍMICA ORGANICA     ¿Qué es la química orgánica?   ¿Por qué la han estudiado tantas personas?   ¿Por qué debes estudiarla?       -organismos vivos... sustancias orgánicas   -proteínas... pelo, piel, músculos   -DNA... herencia genética   -alimentos   -prendas   -medicinas      Cualquiera que muestre cierta curiosidad por la vida y las cosas vivientes, debe tener un conocimiento básico de la química orgánica.
    2. 5. QUÍMICA ORGÁNICA estudio de los compuestos de carbono
    3. 6. Nomenclatura IUPAC de Alcanos NO Ramificados
    4. 7. <ul><li>Recordar: </li></ul><ul><ul><li>metano CH 4 </li></ul></ul><ul><ul><li>etano CH 3 CH 3 </li></ul></ul><ul><ul><li>propano CH 3 CH 2 CH 3 </li></ul></ul><ul><ul><li>butano CH 3 CH 2 CH 2 CH 3 </li></ul></ul>Nombres IUPAC de Alcanos No Ramificados
    5. 8. Nombres IUPAC de Alcanos No Ramificados <ul><li>Nota: el prefijo n no es parte del nombre IUPAC de ningún alcano. </li></ul><ul><li>Por ejemplo: n -butano es el “nombre común&quot; para CH 3 CH 2 CH 2 CH 3 ; butano es el “nombre IUPAC.&quot; </li></ul><ul><li>Otros: </li></ul><ul><ul><li>Prefijos Latinos o Griegos para el número de carbonos + el sufijo ano. </li></ul></ul>
    6. 9. <ul><li># de carbonos Nombre Estructura </li></ul><ul><li>5 pentano CH 3 (CH 2 ) 3 CH 3 </li></ul><ul><li>6 hexano CH 3 (CH 2 ) 4 CH 3 </li></ul><ul><li>7 heptano CH 3 (CH 2 ) 5 CH 3 </li></ul><ul><li>8 octano CH 3 (CH 2 ) 6 CH 3 </li></ul><ul><li>9 nonano CH 3 (CH 2 ) 7 CH 3 </li></ul><ul><li>10 decano CH 3 (CH 2 ) 8 CH 3 </li></ul>Nombres IUPAC de Alcanos No Ramificados
    7. 10. <ul><li># de carbonos Nombre Estructura </li></ul><ul><li>11 undecano CH 3 (CH 2 ) 9 CH 3 </li></ul><ul><li>12 dodecano CH 3 (CH 2 ) 10 CH 3 </li></ul><ul><li>13 tridecano CH 3 (CH 2 ) 11 CH 3 </li></ul><ul><li>14 tetradecano CH 3 (CH 2 ) 12 CH 3 </li></ul><ul><li>15 pentadecano CH 3 (CH 2 ) 7 CH 3 </li></ul><ul><li>16 hexadecano CH 3 (CH 2 ) 8 CH 3 </li></ul>Nombres IUPAC de Alcanos No Ramificados
    8. 11. <ul><li># de carbonos Nombre Estructura </li></ul><ul><li>17 heptadecano CH 3 (CH 2 ) 15 CH 3 </li></ul><ul><li>18 octadecano CH 3 (CH 2 ) 16 CH 3 </li></ul><ul><li>19 nonadecano CH 3 (CH 2 ) 17 CH 3 </li></ul><ul><li>20 icosano CH 3 (CH 2 ) 18 CH 3 </li></ul><ul><li>25 pentacosano CH 3 (CH 2 ) 22 CH 3 </li></ul><ul><li>30 triacontano CH 3 (CH 2 ) 28 CH 3 </li></ul>Nombres IUPAC de Alcanos No Ramificados
    9. 12. Aplicación de las Reglas de la IUPAC: Los Nombres de los Isómeros C 6 H 14
    10. 13. Los Isómeros C 6 H 14 CH 3 CH 2 CH 2 CH 2 CH 2 CH 3 (CH 3 ) 2 CHCH 2 CH 2 CH 3 (CH 3 CH 2 ) 2 CHCH 3 (CH 3 ) 2 CHCH(CH 3 ) 2 (CH 3 ) 3 CCH 2 CH 3
    11. 14. <ul><li>El nombre IUPAC del alcano no ramificado con una cadena de 6 carbonos es hexano. </li></ul>Los Isómeros C 6 H 14 CH 3 CH 2 CH 2 CH 2 CH 2 CH 3 Hexano
    12. 15. Nomenclatura IUPAC de Alcanos Ramificados 1) Selecciona la cadena de carbonos continua más larga y usar el nombre IUPAC del alcano no ramificado como base. 2) Identifica los grupos sustituyentes unidos a la cadena base. 3) Enumera la cadena continua más larga en la dirección que da el número más bajo al grupo sustituyente en el primer punto de ramificación.
    13. 16. Los Isómeros C 6 H 14 (CH 3 ) 2 CHCH 2 CH 2 CH 3 (CH 3 CH 2 ) 2 CHCH 3 2-Metilpentano 3-Metilpentano
    14. 17. <ul><li>Usa prefijos multiplicadores (di-, tri-, tetra-, etc.) de acuerdo al número de sustituyentes idénticos unidos a la cadena principal. </li></ul>Los Isómeros C 6 H 14 (CH 3 ) 2 CHCH(CH 3 ) 2 (CH 3 ) 3 CCH 2 CH 3 2,3-Dimetilbutano 2,2-Dimetilbutano
    15. 18. Grupos Alquilo
    16. 19. Grupos Metilo y Etilo Metilo Etilo o o C C H H H H H CH 3 CH 2 C H H H CH 3
    17. 20. Grupos Alquilo no Ramificados Si el punto de unión está en un extremo de la cadena, en la nomenclatura IUPAC, se nombra reemplazando la terminación – ano por -i lo . R H R
    18. 21. Grupos Alquilo no Ramificados Butilo o Si el punto de unión está en un extremo de la cadena, en la nomenclatura IUPAC, se nombra reemplazando la terminación – ano por -i lo . R H R CH 3 CH 2 CH 2 CH 2 C C H H H H H C C H H H H
    19. 22. Grupos Alquilo no Ramificados Hexilo Heptilo Octadecilo CH 3 (CH 2 ) 4 CH 2 CH 3 (CH 2 ) 5 CH 2 CH 3 (CH 2 ) 16 CH 2
    20. 23. Los Grupos Alquilo C 3 H 7 CH 3 CH 2 CH 2 C C H H H H H C H H o y CH 3 CHCH 3 C C H H H H H C H H o
    21. 24. <ul><li>Nombre IUPAC: Propilo </li></ul><ul><li>Nombre común : n -Propilo </li></ul>Los Grupos Alquilo C 3 H 7 CH 3 CH 2 CH 2 C C H H H H H C H H o
    22. 25. Nombrando a los Grupos Alquilo 1: Identifica la cadena contínua más larga comenzando en el punto de unión. 2: Drop - ane ending from name of unbranched alkane having same number of carbons as longest continuous chain and replace by - yl . 3: Identifica los sustituyentes en la cadena continua más larga. 4: La cadena siempre se numera comenzando en el punto de union.
    23. 26. <ul><li>Nombre IUPAC : 1-Metiletilo </li></ul><ul><li>Nombre común : Isopropilo </li></ul>Los Grupos Alquilo C 3 H 7 CH 3 CHCH 3 C C H H H H C H H o H
    24. 27. <ul><li>Classification: Primary alkyl group </li></ul><ul><li>Alkyl groups are classified according to the degree of substitution at the carbon that bears the point of attachment. A carbon that is directly attached to one other carbon is a primary carbon. </li></ul>The C 3 H 7 Alkyl Groups CH 3 CH 2 CH 2 C C H H H H H C H H or
    25. 28. <ul><li>Classification: Secondary alkyl group </li></ul><ul><li>Alkyl groups are classified according to the degree of substitution at the carbon that bears the point of attachment. A carbon that is directly attached to two other carbons is a secondary carbon. </li></ul>The C 3 H 7 Alkyl Groups CH 3 CHCH 3 C C H H H H C H H or H
    26. 29. <ul><li>IUPAC name: Butyl </li></ul><ul><li>Common name: n -Butyl </li></ul><ul><li>Classification: Primary alkyl group </li></ul>The C 4 H 9 Alkyl Groups CH 3 CH 2 CH 2 CH 2 C C H H H H H C C H H H H or
    27. 30. <ul><li>IUPAC name: 1-Methylpropyl </li></ul><ul><li>Common name: sec -Butyl </li></ul><ul><li>Classification: Secondary alkyl group </li></ul>The C 4 H 9 Alkyl Groups CH 3 CHCH 2 CH 3 C C H H H H H C C H H H H or 1 2 3
    28. 31. <ul><li>IUPAC name: 2-Methylpropyl </li></ul><ul><li>Common name: Isobutyl </li></ul><ul><li>Classification: Primary alkyl group </li></ul>The C 4 H 9 Alkyl Groups 1 2 3 C H CH 2 CH 3 CH 3
    29. 32. <ul><li>IUPAC name: 1,1-Dimethylethyl </li></ul><ul><li>Common name: tert -Butyl </li></ul><ul><li>Classification: Tertiary alkyl group </li></ul>The C 4 H 9 Alkyl Groups 1 2 C CH 3 CH 3 CH 3
    30. 33. Nombres IUPAC de Alcanos Altamente Ramificados
    31. 34. Branched alkanes <ul><li>Octane </li></ul>
    32. 35. <ul><li>4-Ethyloctane </li></ul>Branched alkanes
    33. 36. <ul><li>4-Ethyl-3-methyloctane </li></ul>Branched alkanes List substituents in alphabetical order.
    34. 37. <ul><li>4-Ethyl-3,5-dimethyloctane </li></ul>Branched alkanes List substituents in alphabetical order. But don't alphabetize di-, tri-, tetra-, etc.
    35. 38. First Point of Difference Rule <ul><li>The chain is numbered in the direction that gives the lower locant to the substituent at the first point of difference in the names. </li></ul><ul><li>Don't add locants! </li></ul>2,2,6,6,7-Pentamethyloctane? 2,3,3,7,7-Pentamethyloctane? What is correct name? 1 2 3 4 5 6 7 8 8 7 6 5 4 3 2 1
    36. 39. First Point of Difference Rule <ul><li>The chain is numbered in the direction that gives the lower locant to the substituent at the first point of difference in the names. </li></ul><ul><li>Don't add locants! </li></ul>2,2,6,6,7-Pentamethyloctane? What is correct name? 8 7 6 5 4 3 2 1
    37. 40. Nomenclatura de Cicloalcanos C n H 2 n
    38. 41. Cycloalkanes <ul><li>Cycloalkanes are alkanes that contain a ring of three or more carbons. </li></ul><ul><li>Count the number of carbons in the ring, and add the prefix cyclo to the IUPAC name of the unbranched alkane that has that number of carbons. </li></ul>Cyclopentane Cyclohexane
    39. 42. Cycloalkanes <ul><li>Name any alkyl groups on the ring in the usual way. </li></ul>Ethylcyclopentane CH 2 CH 3
    40. 43. <ul><li>Name any alkyl groups on the ring in the usual way. </li></ul><ul><li>List substituents in alphabetical order and count in the direction that gives the lowest numerical locant at the first point of difference. </li></ul>Cycloalkanes 3-Ethyl-1,1-dimethylcyclohexane CH 2 CH 3 H 3 C CH 3
    41. 44. Nomenclatura de Alquenos
    42. 45. Alkenes <ul><li>Alkenes are hydrocarbons that contain a carbon-carbon double bond </li></ul><ul><li>also called &quot;olefins&quot; </li></ul><ul><li>characterized by molecular formula C n H 2n </li></ul><ul><li>said to be &quot;unsaturated&quot; </li></ul>
    43. 46. Alkene Nomenclature Ethene or Ethylene (both are acceptable IUPAC names) Propene (Propylene is sometimes used but is not an acceptable IUPAC name) H 2 C CH 2 H 2 C CHCH 3
    44. 47. <ul><li>1) Find the longest continuous chain that includes the double bond. </li></ul><ul><li>2) Replace the - ane ending of the unbranched alkane having the same number of carbons by - ene . </li></ul><ul><li>3) Number the chain in the direction that gives the lowest number to the doubly bonded carbon. </li></ul>1-Butene Alkene Nomenclature H 2 C CHCH 2 CH 3
    45. 48. <ul><li>4) If a substituent is present, identify its position by number. The double bond takes precedence over alkyl groups and halogens when the chain is numbered. </li></ul><ul><li>The compound shown above is 4-bromo-3-methyl-1-butene. </li></ul>Alkene Nomenclature H 2 C CHCHCH 2 Br CH 3
    46. 49. <ul><li>4) If a substituent is present, identify its position by number. Hydroxyl groups take precedence over the double bond when the chain is numbered. </li></ul><ul><li>The compound shown above is 2-methyl-3-buten-1-ol. </li></ul>Alkene Nomenclature H 2 C CHCHCH 2 OH CH 3
    47. 50. <ul><li>methylene </li></ul><ul><li>vinyl </li></ul><ul><li>allyl </li></ul><ul><li>isopropenyl </li></ul>Alkenyl Groups CH H 2 C CHCH 2 H 2 C H 2 C CCH 3 H 2 C
    48. 51. Cycloalkene Nomenclature <ul><li>1) Replace the - ane ending of the cycloalkane having the same number of carbons by - ene . </li></ul>Cyclohexene
    49. 52. <ul><li>1) Replace the - ane ending of the cycloalkane having the same number of carbons by - ene . </li></ul><ul><li>2) Number through the double bond in the direction that gives the lower number to the first-appearing substituent. </li></ul>Cycloalkene Nomenclature 6-Ethyl-1-methylcyclohexene CH 3 CH 2 CH 3 1 2 3 4 5 6
    50. 53. Alquinos
    51. 54. Nomenclature
    52. 55. Nomenclature Higher alkynes are named in much the same way as alkenes except using an - yne suffix instead of - ene . HC CH <ul><ul><li>Acetylene and ethyne are both acceptable IUPAC names for </li></ul></ul>HC CCH 3 Propyne HC CCH 2 CH 3 1-Butyne (CH 3 ) 3 CC CCH 3 4,4-Dimethyl-2-pentyne
    53. 56. Functional Groups
    54. 57. <ul><li>a structural unit in a molecule responsible for its characteristic behavior under a particular set of reaction conditions </li></ul>Functional Group
    55. 58. <ul><li>Alcohol ROH </li></ul><ul><li>Alkyl halide R X ( X = F, Cl, Br, I) </li></ul><ul><li>Amine primary amine: R NH 2 </li></ul><ul><li>secondary amine: R 2 NH </li></ul><ul><li>tertiary amine: R 3 N </li></ul>Families of organic compounds and their functional groups
    56. 59. <ul><li>Ether R O R' </li></ul><ul><li>Nitrile R CN </li></ul><ul><li>Nitroalkane R NO 2 </li></ul><ul><li>Sulfide RSR' </li></ul><ul><li>Thiol RSH </li></ul>Families of organic compounds and their functional groups Epoxide C C O
    57. 60. Many classes of organic compounds contain a carbonyl group Carbonyl group Acyl group R O C O C
    58. 61. Many classes of organic compounds contain a carbonyl group Carbonyl group Aldehyde R H O C O C
    59. 62. Many classes of organic compounds contain a carbonyl group Carbonyl group Ketone R R' O C O C
    60. 63. Many classes of organic compounds contain a carbonyl group Carbonyl group Carboxylic acid R OH O C O C
    61. 64. Many classes of organic compounds contain a carbonyl group Carbonyl group Ester R OR' O C O C
    62. 65. Many classes of organic compounds contain a carbonyl group Carbonyl group Amide R NH 2 O C O C
    63. 66. IUPAC Nomenclature of Alkyl Halides
    64. 67. <ul><li>The two that are most widely used are: functional class nomenclature substitutive nomenclature </li></ul><ul><li>Both types can be applied to alcohols and alkyl halides. </li></ul>IUPAC Nomenclature There are several kinds of IUPAC nomenclature.
    65. 68. <ul><li>Name the alkyl group and the halogen as separate words ( alkyl + halide ) </li></ul>Functional Class Nomenclature of Alkyl Halides CH 3 F CH 3 CH 2 CH 2 CH 2 CH 2 Cl CH 3 CH 2 CHCH 2 CH 2 CH 3 Br H I
    66. 69. <ul><li>Name the alkyl group and the halogen as separate words ( alkyl + halide ) </li></ul>Functional Class Nomenclature of Alkyl Halides CH 3 F CH 3 CH 2 CH 2 CH 2 CH 2 Cl Methyl fluoride Pentyl chloride 1-Ethylbutyl bromide Cyclohexyl iodide CH 3 CH 2 CHCH 2 CH 2 CH 3 Br H I
    67. 70. <ul><li>Name as halo-substituted alkanes. </li></ul><ul><li>Number the longest chain containing the halogen in the direction that gives the lowest number to the substituted carbon. </li></ul>Substitutive Nomenclature of Alkyl Halides CH 3 CH 2 CH 2 CH 2 CH 2 F CH 3 CHCH 2 CH 2 CH 3 Br CH 3 CH 2 CHCH 2 CH 3 I
    68. 71. <ul><li>Name as halo-substituted alkanes. </li></ul><ul><li>Number the longest chain containing the halogen in the direction that gives the lowest number to the substituted carbon. </li></ul>Substitutive Nomenclature of Alkyl Halides CH 3 CH 2 CH 2 CH 2 CH 2 F 1-Fluoropentane 3-Iodopentane 2-Bromopentane CH 3 CHCH 2 CH 2 CH 3 Br CH 3 CH 2 CHCH 2 CH 3 I
    69. 72. Substitutive Nomenclature of Alkyl Halides <ul><li>Halogen and alkyl groups are of equal rank when it comes to numbering the chain. </li></ul><ul><li>Number the chain in the direction that gives the lowest number to the group (halogen or alkyl) that appears first. </li></ul>CH 3 Cl Cl CH 3
    70. 73. Substitutive Nomenclature of Alkyl Halides 5-Chloro-2-methylheptane 2-Chloro-5-methylheptane CH 3 Cl Cl CH 3
    71. 74. IUPAC Nomenclature of Alcohols
    72. 75. <ul><li>Name the alkyl group and add &quot;alcohol&quot; as a separate word. </li></ul>Functional Class Nomenclature of Alcohols CH 3 CH 2 OH CH 3 CHCH 2 CH 2 CH 2 CH 3 OH CH 3 CCH 2 CH 2 CH 3 OH CH 3
    73. 76. <ul><li>Name the alkyl group and add &quot;alcohol&quot; as a separate word. </li></ul>Functional Class Nomenclature of Alcohols CH 3 CH 2 OH Ethyl alcohol 1-Methylpentyl alcohol 1,1-Dimethylbutyl alcohol CH 3 CHCH 2 CH 2 CH 2 CH 3 OH CH 3 CCH 2 CH 2 CH 3 OH CH 3
    74. 77. <ul><li>Name as &quot;alkanols.&quot; Replace -e ending of alkane name by -ol. </li></ul><ul><li>Number chain in direction that gives lowest number to the carbon that bears the —OH group. </li></ul>Substitutive Nomenclature of Alcohols CH 3 CH 2 OH CH 3 CHCH 2 CH 2 CH 2 CH 3 OH CH 3 CCH 2 CH 2 CH 3 OH CH 3
    75. 78. <ul><li>Name as &quot;alkanols.&quot; Replace -e ending of alkane name by -ol. </li></ul><ul><li>Number chain in direction that gives lowest number to the carbon that bears the —OH group. </li></ul>Substitutive Nomenclature of Alcohols CH 3 CH 2 OH Ethanol 2-Hexanol 2-Methyl-2-pentanol CH 3 CHCH 2 CH 2 CH 2 CH 3 OH CH 3 CCH 2 CH 2 CH 3 OH CH 3
    76. 79. Substitutive Nomenclature of Alcohols <ul><li>Hydroxyl groups outrank alkyl groups when it comes to numbering the chain. </li></ul><ul><li>Number the chain in the direction that gives the lowest number to the carbon that bears the OH group </li></ul>OH CH 3 CH 3 OH
    77. 80. Substitutive Nomenclature of Alcohols 6-Methyl-3-heptanol 5-Methyl-2-heptanol OH CH 3 CH 3 OH
    78. 81. Classes of Alcohols and Alkyl Halides
    79. 82. <ul><li>Alcohols and alkyl halides are classified as primary secondary tertiary according to their &quot;degree of substitution.&quot; </li></ul><ul><li>Degree of substitution is determined by counting the number of carbon atoms directly attached to the carbon that bears the halogen or hydroxyl group. </li></ul>Classification
    80. 83. Classification CH 3 CH 2 CH 2 CH 2 C H 2 F primary alkyl halide secondary alkyl halide tertiary alcohol H OH secondary alcohol CH 3 C HCH 2 CH 2 CH 3 Br CH 3 C CH 2 CH 2 CH 3 OH CH 3
    81. 84. Ethers, Epoxides, and Sulfides
    82. 85. Nomenclature of Ethers, Epoxides, and Sulfides
    83. 86. <ul><li>name as alkoxy derivatives of alkanes </li></ul>Substitutive IUPAC Names of Ethers CH 3 O CH 2 CH 3 methoxy ethane CH 3 CH 2 O CH 2 CH 3 ethoxy ethane CH 3 CH 2 O CH 2 CH 2 CH 2 Cl 1-chloro-3- ethoxy propane
    84. 87. <ul><li>name the groups attached to oxygen in alphabetical order as separate words; &quot;ether&quot; is last word </li></ul>Functional Class IUPAC Names of Ethers CH 3 O CH 2 CH 3 ethyl methyl ether CH 3 CH 2 O CH 2 CH 3 di ethyl ether CH 3 CH 2 O CH 2 CH 2 CH 2 Cl 3-chloropropyl ethyl ether
    85. 88. <ul><li>name as alkylthio derivatives of alkanes </li></ul>Substitutive IUPAC Names of Sulfides CH 3 S CH 2 CH 3 methylthio ethane CH 3 CH 2 S CH 2 CH 3 ethylthio ethane (methylthio)cyclopentane SCH 3
    86. 89. <ul><li>analogous to ethers, but replace “ether” as last word in the name by “sulfide.” </li></ul>Functional Class IUPAC Names of Sulfides cyclopentyl methyl sulfide CH 3 S CH 2 CH 3 ethyl methyl sulfide CH 3 CH 2 S CH 2 CH 3 di ethyl sulfide S CH 3
    87. 90. Names of Cyclic Ethers O O O O O O Oxirane (Ethylene oxide) Oxetane Oxolane (tetrahydrofuran) Oxane (tetrahydropyran) 1,4-Dioxane
    88. 91. Names of Cyclic Sulfides S S S S Thiirane Thietane Thiolane Thiane
    89. 92. Amines
    90. 93. Amine Nomenclature
    91. 94. <ul><li>Alkylamine </li></ul><ul><ul><li>N attached to alkyl group </li></ul></ul><ul><li>Arylamine </li></ul><ul><ul><li>N attached to aryl group </li></ul></ul><ul><li>Primary, secondary, or tertiary </li></ul><ul><ul><li>determined by number of carbon atoms directly attached to nitrogen </li></ul></ul>Classification of Amines
    92. 95. <ul><li>Two IUPAC styles </li></ul><ul><li>1) analogous to alcohols: replace - e ending by - anamine </li></ul><ul><li>2) name alkyl group and attach - amine as a suffix </li></ul>Nomenclature of Primary Alkylamines (RNH 2 )
    93. 96. Examples: some primary alkylamines (RNH 2 : one carbon directly attached to N) CH 3 CH 2 N H 2 ethylamine or ethanamine cyclohexylamine or cyclohexanamine 1-methylbutylamine or 2-pentanamine CH 3 CHCH 2 CH 2 CH 3 N H 2 N H 2
    94. 97. <ul><li>Name as derivatives of aniline. </li></ul>Nomenclature of Primary Arylamines (ArNH 2 ) p -fluoroaniline 5-bromo-2-ethylaniline N H 2 F N H 2 Br CH 2 CH 3
    95. 98. Amino groups as substituents <ul><li>amino groups rank below OH groups and higher oxidation states of carbon </li></ul><ul><li>in such cases name the amino group as a substituent </li></ul>p -aminobenzaldehyde H O CH 2 CH 2 N H 2 2-aminoethanol N H 2 H C O
    96. 99. <ul><li>Name as N -substituted derivatives of parent primary amine. </li></ul><ul><li>(N is a locant-it is not alphabetized, but is treated the same way as a numerical locant) </li></ul><ul><li>Parent amine is one with longest carbon chain. </li></ul>Secondary and Tertiary Amines
    97. 100. Examples CH 3 N HCH 2 CH 3 N -methylethylamine 4-chloro- N -ethyl-3-nitroaniline N , N -dimethylcycloheptylamine N HCH 2 CH 3 NO 2 Cl CH 3 N CH 3
    98. 101. <ul><li>A nitrogen with four substituents is positively charged and is named as a derivative of ammonium ion (NH 4 + ). </li></ul>Ammonium Salts CH 3 NH 3 + methylammonium chloride N -ethyl- N -methylcyclopentylammonium trifluoroacetate Cl – N CH 3 H CH 2 CH 3 + CF 3 CO 2 –
    99. 102. <ul><li>When all four atoms attached to N are carbon, the ion is called a quaternary ammonium ion and salts that contain it are called quaternary ammonium salts. </li></ul>Ammonium Salts benzyltrimethylammonium iodide + CH 2 N CH 3 CH 3 CH 3 I –
    100. 103. Nomenclature
    101. 104. IUPAC Nomenclature of Aldehydes Base the name on the chain that contains the carbonyl group and replace the -e ending of the hydrocarbon by -al . H O O H O HCCHCH O
    102. 105. IUPAC Nomenclature of Aldehydes 4,4-dimethylpent an al 5-hex en al 2-phenylprop ane dial (keep the -e ending before -dial ) H O O H O HCCHCH O
    103. 106. IUPAC Nomenclature of Aldehydes when named as a substituent formyl group carbaldehyde or carboxaldehyde when named as a suffix C H O
    104. 107. Substitutive IUPAC Nomenclature of Ketones Base the name on the chain that contains the carbonyl group and replace -e by -one . Number the chain in the direction that gives the lowest number to the carbonyl carbon. CH 3 CH 2 CCH 2 CH 2 CH 3 O CH 3 CHCH 2 CCH 3 O CH 3 H 3 C O
    105. 108. Substitutive IUPAC Nomenclature of Ketones 3- hexan one 4-methyl -2- pentan one 4-methylcyclohexan one CH 3 CH 2 CCH 2 CH 2 CH 3 O CH 3 CHCH 2 CCH 3 O CH 3 H 3 C O
    106. 109. Functional Class IUPAC Nomenclature of Ketones List the groups attached to the carbonyl separately in alphabetical order, and add the word ketone . CH 3 CH 2 C CH 2 CH 2 CH 3 O O CH 2 C CH 2 CH 3 CH CH 2 O H 2 C CHC
    107. 110. Functional Class IUPAC Nomenclature of Ketones ethyl propyl ketone benzyl ethyl ketone divinyl ketone CH 3 CH 2 C CH 2 CH 2 CH 3 O O CH 2 C CH 2 CH 3 CH CH 2 O H 2 C CHC
    108. 111. Carboxylic Acids
    109. 112. Carboxylic Acid Nomenclature
    110. 113. <ul><ul><li>systematic IUPAC names replace &quot;-e&quot; ending of alkane with &quot;oic acid&quot; </li></ul></ul>Systematic Name O HCOH O CH 3 COH O CH 3 (CH 2 ) 16 COH methanoic acid ethanoic acid octadecanoic acid
    111. 114. <ul><ul><li>common names are based on natural origin rather than structure </li></ul></ul>Systematic Name Common Name methanoic acid formic acid ethanoic acid acetic acid octadecanoic acid stearic acid O HCOH O CH 3 COH O CH 3 (CH 2 ) 16 COH
    112. 115. Systematic Name Common Name 2-hydroxypropanoic acid lactic acid ( Z )-9-octadecenoic acid oleic acid O CH 3 CHCOH OH O (CH 2 ) 7 COH C C H H CH 3 (CH 2 ) 7
    113. 116. Nomenclature of Carboxylic Acid Derivatives
    114. 117. Acyl Halides <ul><li>name the acyl group and add the word chloride , fluoride , bromide , or iodide as appropriate </li></ul><ul><li>acyl chlorides are, by far, the most frequently encountered of the acyl halides </li></ul>RC O X
    115. 118. Acyl Halides acetyl chloride 3-butenoyl chloride p -fluorobenzoyl bromide CH 3 C Cl O O H 2 C CHCH 2 C Cl O C Br F
    116. 119. Acid Anhydrides <ul><li>when both acyl groups are the same, name the acid and add the word anhydride </li></ul><ul><li>when the groups are different, list the names of the corresponding acids in alphabetical order and add the word anhydride </li></ul>RC O CR' O O
    117. 120. Acid Anhydrides acetic anhydride benzoic anhydride benzoic heptanoic anhydride CH 3 C O CCH 3 O O C 6 H 5 C O CC 6 H 5 O O C 6 H 5 C O C(CH 2 ) 5 CH 3 O O
    118. 121. Esters <ul><li>name as alkyl alkanoates </li></ul><ul><li>cite the alkyl group attached to oxygen first (R') </li></ul><ul><li>name the acyl group second; substitute the suffix -ate for the -ic ending of the corresponding acid </li></ul>RC O R' O
    119. 122. Esters ethyl acetate methyl propanoate 2-chloroethyl benzoate CH 3 C O CH 2 CH 3 O O CH 3 CH 2 C O CH 3 C O CH 2 CH 2 Cl O
    120. 123. Amides having an NH 2 group <ul><li>identify the corresponding carboxylic acid </li></ul><ul><li>replace the -ic acid or -oic acid ending by -amide </li></ul>RC N H 2 O
    121. 124. Amides having an NH 2 group acet amide 3-methylbutan amide benz amide CH 3 C N H 2 O O (CH 3 ) 2 CHCH 2 C N H 2 C N H 2 O
    122. 125. Amides having substituents on N <ul><li>name the amide as before </li></ul><ul><li>precede the name of the amide with the name of the appropriate group or groups </li></ul><ul><li>precede the names of the groups by the letter N- (standing for nitrogen and used as a locant) </li></ul>and RC N H R' O RC N R' 2 O
    123. 126. Amides having substituents on N N - methyl acetamide N - isopropyl - N - methyl butanamide N , N - diethyl benzamide CH 3 C N H CH 3 O C N (CH 2 CH 3 ) 2 O O CH 3 CH 2 CH 2 C N CH(CH 3 ) 2 CH 3
    124. 127. Nitriles <ul><li>add the suffix -nitrile to the name of the parent hydrocarbon chain (including the triply bonded carbon of CN) </li></ul><ul><li>or: replace the -ic acid or -oic acid name of the corresponding carboxylic acid by -onitrile </li></ul><ul><li>or: name as an alkyl cyanide (functional class name) </li></ul>RC N
    125. 128. Nitriles ethanenitrile or: acetonitrile or: methyl cyanide benzonitrile 2-methylpropanenitrile or: isopropyl cyanide CH 3 C N C 6 H 5 C N N C CH 3 CHCH 3

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