Nomenclatura

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.

QUÍMICA ORGÁNICA estudio de los compuestos de carbono

Nomenclatura IUPAC de Alcanos NO Ramificados

Recordar: metano CH 4 etano CH 3 CH 3 propano CH 3 CH 2 CH 3 butano CH 3 CH 2 CH 2 CH 3 Nombres IUPAC de Alcanos No Ramificados

Nombres IUPAC de Alcanos No Ramificados Nota: el prefijo n no es parte del nombre IUPAC de ningún alcano. Por ejemplo: n -butano es el “nombre común" para CH 3 CH 2 CH 2 CH 3 ; butano es el “nombre IUPAC." Otros: Prefijos Latinos o Griegos para el número de carbonos + el sufijo ano.

# de carbonos Nombre Estructura 5 pentano CH 3 (CH 2 ) 3 CH 3 6 hexano CH 3 (CH 2 ) 4 CH 3 7 heptano CH 3 (CH 2 ) 5 CH 3 8 octano CH 3 (CH 2 ) 6 CH 3 9 nonano CH 3 (CH 2 ) 7 CH 3 10 decano CH 3 (CH 2 ) 8 CH 3 Nombres IUPAC de Alcanos No Ramificados

# de carbonos Nombre Estructura 11 undecano CH 3 (CH 2 ) 9 CH 3 12 dodecano CH 3 (CH 2 ) 10 CH 3 13 tridecano CH 3 (CH 2 ) 11 CH 3 14 tetradecano CH 3 (CH 2 ) 12 CH 3 15 pentadecano CH 3 (CH 2 ) 7 CH 3 16 hexadecano CH 3 (CH 2 ) 8 CH 3 Nombres IUPAC de Alcanos No Ramificados

# de carbonos Nombre Estructura 17 heptadecano CH 3 (CH 2 ) 15 CH 3 18 octadecano CH 3 (CH 2 ) 16 CH 3 19 nonadecano CH 3 (CH 2 ) 17 CH 3 20 icosano CH 3 (CH 2 ) 18 CH 3 25 pentacosano CH 3 (CH 2 ) 22 CH 3 30 triacontano CH 3 (CH 2 ) 28 CH 3 Nombres IUPAC de Alcanos No Ramificados

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 ) 2 (CH 3 ) 3 CCH 2 CH 3

El nombre IUPAC del alcano no ramificado con una cadena de 6 carbonos es hexano. Los Isómeros C 6 H 14 CH 3 CH 2 CH 2 CH 2 CH 2 CH 3 Hexano

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.

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

Usa prefijos multiplicadores (di-, tri-, tetra-, etc.) de acuerdo al número de sustituyentes idénticos unidos a la cadena principal. 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

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 reemplazando la terminación – ano por -i lo . R H R

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

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

Nombre IUPAC: Propilo Nombre común : n -Propilo Los Grupos Alquilo C 3 H 7 CH 3 CH 2 CH 2 C C H H H H H C H H o

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.

Nombre IUPAC : 1-Metiletilo Nombre común : Isopropilo Los Grupos Alquilo C 3 H 7 CH 3 CHCH 3 C C H H H H C H H o H

Classification: Primary alkyl group 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. The C 3 H 7 Alkyl Groups CH 3 CH 2 CH 2 C C H H H H H C H H or

Classification: Secondary alkyl group 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. The C 3 H 7 Alkyl Groups CH 3 CHCH 3 C C H H H H C H H or H

IUPAC name: Butyl Common name: n -Butyl Classification: Primary alkyl group 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

IUPAC name: 1-Methylpropyl Common name: sec -Butyl Classification: Secondary alkyl group 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

IUPAC name: 2-Methylpropyl Common name: Isobutyl Classification: Primary alkyl group The C 4 H 9 Alkyl Groups 1 2 3 C H CH 2 CH 3 CH 3

IUPAC name: 1,1-Dimethylethyl Common name: tert -Butyl Classification: Tertiary alkyl group The C 4 H 9 Alkyl Groups 1 2 C CH 3 CH 3 CH 3

Nombres IUPAC de Alcanos Altamente Ramificados

4-Ethyloctane Branched alkanes

4-Ethyl-3-methyloctane Branched alkanes List substituents in alphabetical order.

4-Ethyl-3,5-dimethyloctane Branched alkanes List substituents in alphabetical order. But don't alphabetize di-, tri-, tetra-, etc.

First Point of Difference Rule The chain is numbered in the direction that gives the lower locant to the substituent at the first point of difference in the names. Don't add locants! 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

First Point of Difference Rule The chain is numbered in the direction that gives the lower locant to the substituent at the first point of difference in the names. Don't add locants! 2,2,6,6,7-Pentamethyloctane? What is correct name? 8 7 6 5 4 3 2 1

Nomenclatura de Cicloalcanos C n H 2 n

Cycloalkanes Cycloalkanes are alkanes that contain a ring of three or more carbons. 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. Cyclopentane Cyclohexane

Cycloalkanes Name any alkyl groups on the ring in the usual way. Ethylcyclopentane CH 2 CH 3

Name any alkyl groups on the ring in the usual way. List substituents in alphabetical order and count in the direction that gives the lowest numerical locant at the first point of difference. Cycloalkanes 3-Ethyl-1,1-dimethylcyclohexane CH 2 CH 3 H 3 C CH 3

Alkenes Alkenes are hydrocarbons that contain a carbon-carbon double bond also called "olefins" characterized by molecular formula C n H 2n said to be "unsaturated"

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

1) Find the longest continuous chain that includes the double bond. 2) Replace the - ane ending of the unbranched alkane having the same number of carbons by - ene . 3) Number the chain in the direction that gives the lowest number to the doubly bonded carbon. 1-Butene Alkene Nomenclature H 2 C CHCH 2 CH 3

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. The compound shown above is 4-bromo-3-methyl-1-butene. Alkene Nomenclature H 2 C CHCHCH 2 Br CH 3

4) If a substituent is present, identify its position by number. Hydroxyl groups take precedence over the double bond when the chain is numbered. The compound shown above is 2-methyl-3-buten-1-ol. Alkene Nomenclature H 2 C CHCHCH 2 OH CH 3

methylene vinyl allyl isopropenyl Alkenyl Groups CH H 2 C CHCH 2 H 2 C H 2 C CCH 3 H 2 C

Cycloalkene Nomenclature 1) Replace the - ane ending of the cycloalkane having the same number of carbons by - ene . Cyclohexene

1) Replace the - ane ending of the cycloalkane having the same number of carbons by - ene . 2) Number through the double bond in the direction that gives the lower number to the first-appearing substituent. Cycloalkene Nomenclature 6-Ethyl-1-methylcyclohexene CH 3 CH 2 CH 3 1 2 3 4 5 6

Nomenclature Higher alkynes are named in much the same way as alkenes except using an - yne suffix instead of - ene . HC CH Acetylene and ethyne are both acceptable IUPAC names for HC CCH 3 Propyne HC CCH 2 CH 3 1-Butyne (CH 3 ) 3 CC CCH 3 4,4-Dimethyl-2-pentyne

a structural unit in a molecule responsible for its characteristic behavior under a particular set of reaction conditions Functional Group

Alcohol ROH Alkyl halide R X ( X = F, Cl, Br, I) Amine primary amine: R NH 2 secondary amine: R 2 NH tertiary amine: R 3 N Families of organic compounds and their functional groups

Ether R O R' Nitrile R CN Nitroalkane R NO 2 Sulfide RSR' Thiol RSH Families of organic compounds and their functional groups Epoxide C C O

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

The two that are most widely used are: functional class nomenclature substitutive nomenclature Both types can be applied to alcohols and alkyl halides. IUPAC Nomenclature There are several kinds of IUPAC nomenclature.

Name the alkyl group and the halogen as separate words ( alkyl + halide ) 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

Name the alkyl group and the halogen as separate words ( alkyl + halide ) 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

Name as halo-substituted alkanes. Number the longest chain containing the halogen in the direction that gives the lowest number to the substituted carbon. 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

Name as halo-substituted alkanes. Number the longest chain containing the halogen in the direction that gives the lowest number to the substituted carbon. 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

Substitutive Nomenclature of Alkyl Halides Halogen and alkyl groups are of equal rank when it comes to numbering the chain. Number the chain in the direction that gives the lowest number to the group (halogen or alkyl) that appears first. CH 3 Cl Cl CH 3

Substitutive Nomenclature of Alkyl Halides 5-Chloro-2-methylheptane 2-Chloro-5-methylheptane CH 3 Cl Cl CH 3

IUPAC Nomenclature of Alcohols

Name the alkyl group and add "alcohol" as a separate word. 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

Name the alkyl group and add "alcohol" as a separate word. 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

Name as "alkanols." Replace -e ending of alkane name by -ol. Number chain in direction that gives lowest number to the carbon that bears the —OH group. 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

Name as "alkanols." Replace -e ending of alkane name by -ol. Number chain in direction that gives lowest number to the carbon that bears the —OH group. 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

Substitutive Nomenclature of Alcohols Hydroxyl groups outrank alkyl groups when it comes to numbering the chain. Number the chain in the direction that gives the lowest number to the carbon that bears the OH group OH CH 3 CH 3 OH

Substitutive Nomenclature of Alcohols 6-Methyl-3-heptanol 5-Methyl-2-heptanol OH CH 3 CH 3 OH

Classes of Alcohols and Alkyl Halides

Alcohols and alkyl halides are classified as primary secondary tertiary according to their "degree of substitution." Degree of substitution is determined by counting the number of carbon atoms directly attached to the carbon that bears the halogen or hydroxyl group. Classification

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

Ethers, Epoxides, and Sulfides

Nomenclature of Ethers, Epoxides, and Sulfides

name as alkoxy derivatives of alkanes 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

name the groups attached to oxygen in alphabetical order as separate words; "ether" is last word 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

name as alkylthio derivatives of alkanes 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

analogous to ethers, but replace “ether” as last word in the name by “sulfide.” 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

Names of Cyclic Ethers O O O O O O Oxirane (Ethylene oxide) Oxetane Oxolane (tetrahydrofuran) Oxane (tetrahydropyran) 1,4-Dioxane

Names of Cyclic Sulfides S S S S Thiirane Thietane Thiolane Thiane

Alkylamine N attached to alkyl group Arylamine N attached to aryl group Primary, secondary, or tertiary determined by number of carbon atoms directly attached to nitrogen Classification of Amines

Two IUPAC styles 1) analogous to alcohols: replace - e ending by - anamine 2) name alkyl group and attach - amine as a suffix Nomenclature of Primary Alkylamines (RNH 2 )

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

Name as derivatives of aniline. Nomenclature of Primary Arylamines (ArNH 2 ) p -fluoroaniline 5-bromo-2-ethylaniline N H 2 F N H 2 Br CH 2 CH 3

Amino groups as substituents amino groups rank below OH groups and higher oxidation states of carbon in such cases name the amino group as a substituent p -aminobenzaldehyde H O CH 2 CH 2 N H 2 2-aminoethanol N H 2 H C O

Name as N -substituted derivatives of parent primary amine. (N is a locant-it is not alphabetized, but is treated the same way as a numerical locant) Parent amine is one with longest carbon chain. Secondary and Tertiary Amines

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

A nitrogen with four substituents is positively charged and is named as a derivative of ammonium ion (NH 4 + ). 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 –

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. Ammonium Salts benzyltrimethylammonium iodide + CH 2 N CH 3 CH 3 CH 3 I –

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

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

IUPAC Nomenclature of Aldehydes when named as a substituent formyl group carbaldehyde or carboxaldehyde when named as a suffix C H O

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

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

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

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

systematic IUPAC names replace "-e" ending of alkane with "oic acid" Systematic Name O HCOH O CH 3 COH O CH 3 (CH 2 ) 16 COH methanoic acid ethanoic acid octadecanoic acid

common names are based on natural origin rather than structure 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

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

Nomenclature of Carboxylic Acid Derivatives

Acyl Halides name the acyl group and add the word chloride , fluoride , bromide , or iodide as appropriate acyl chlorides are, by far, the most frequently encountered of the acyl halides RC O X

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 when both acyl groups are the same, name the acid and add the word anhydride when the groups are different, list the names of the corresponding acids in alphabetical order and add the word anhydride RC O CR' O O

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

Esters name as alkyl alkanoates cite the alkyl group attached to oxygen first (R') name the acyl group second; substitute the suffix -ate for the -ic ending of the corresponding acid RC O R' O

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

Amides having an NH 2 group identify the corresponding carboxylic acid replace the -ic acid or -oic acid ending by -amide RC N H 2 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 name the amide as before precede the name of the amide with the name of the appropriate group or groups precede the names of the groups by the letter N- (standing for nitrogen and used as a locant) and RC N H R' O RC N R' 2 O

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

Nitriles add the suffix -nitrile to the name of the parent hydrocarbon chain (including the triply bonded carbon of CN) or: replace the -ic acid or -oic acid name of the corresponding carboxylic acid by -onitrile or: name as an alkyl cyanide (functional class name) RC N

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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