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.

Alquimia---------química orgánica

minerales-fuentes vivas

aislar y purificar... descomposición

En 1770, Torbern Bergman, primero en señalar las diferencias... química de los compuestos que se encuentran en organismos vivos.

Fuerza vital--------preparación

En 1816, Michel Chevreul

En 1828, Friedrich Wöhler

... todas las sustancias orgánicas contienen al elemento carbono

QUÍMICA ORGÁNICA estudio de los compuestos de carbono

Nomenclatura IUPAC deNomenclatura IUPAC de Alcanos Alcanos NONO RamificadosRamificados

Recordar:Recordar:

metanometano CHCH44

etanoetano CHCH33CHCH33

propanopropano CHCH33CHCH22CHCH33

butanobutanoCHCH33CHCH22CHCH22CHCH33

Nombres IUPAC de Alcanos No RamificadosNombres IUPAC de Alcanos No Ramificados


Nota:Nota:el prefijo el prefijo nn no es parte del nombre IUPAC de no es parte del nombre IUPAC deningún alcano.ningún alcano.

Por ejemplo: Por ejemplo: nn-butano es el “nombre común" -butano es el “nombre común" para CHpara CH33CHCH22CHCH22CHCH33;; butano es el “nombre butano es el “nombre

IUPAC."IUPAC."

Otros:Otros:

Prefijos Latinos o Griegos para el número de Prefijos Latinos o Griegos para el número de

carbonos + el sufijo ano.carbonos + el sufijo ano.

# de carbonos # de carbonos NombreNombre EstructuraEstructura

55 pentanopentano CHCH33(CH(CH22))33CHCH33

66 hexanohexano CHCH33(CH(CH22))44CHCH33

77 heptanoheptano CHCH33(CH(CH22))55CHCH33

88 octanooctano CHCH33(CH(CH22))66CHCH33

99 nonanononano CHCH33(CH(CH22))77CHCH33

1010 decanodecano CHCH33(CH(CH22))88CHCH33



1111 undecanoundecano CHCH33(CH(CH22))99CHCH33

1212 dodecanododecano CHCH33(CH(CH22))1010CHCH33

1313 tridecanotridecano CHCH33(CH(CH22))1111CHCH33

1414 tetradecanotetradecano CHCH33(CH(CH22))1212CHCH33

1515 pentadecanopentadecano CHCH33(CH(CH22))77CHCH33

1616 hexadecanohexadecano CHCH33(CH(CH22))88CHCH33



1717 heptadecanoheptadecano CHCH33(CH(CH22))1515CHCH33

1818 octadecanooctadecano CHCH33(CH(CH22))1616CHCH33

1919 nonadecanononadecano CHCH33(CH(CH22))1717CHCH33

2020 icosanoicosano CHCH33(CH(CH22))1818CHCH33

2525 pentacosanopentacosano CHCH33(CH(CH22))2222CHCH33

3030 triacontanotriacontano CHCH33(CH(CH22))2828CHCH33


Aplicación de las Reglas Aplicación de las Reglas de la IUPAC:de la IUPAC:

Los Nombres de los Isómeros CLos Nombres de los Isómeros C66HH1414

CHCH33CHCH22CHCH22CHCH22CHCH22CHCH33

(CH(CH33))22CHCHCHCH22CHCH22CHCH33

(CH(CH33CHCH22))22CHCHCHCH33

(CH(CH33))22CHCH(CHCHCH(CH33))22

(CH(CH33))33CCHCCH22CHCH33

Los Isómeros CLos Isómeros C66HH1414

CHCH33CHCH22CHCH22CHCH22CHCH22CHCH33

El nombre IUPAC del alcano no ramificadoEl nombre IUPAC del alcano no ramificadocon una cadena de 6 carbonos es hexano.con una cadena de 6 carbonos es hexano.

HexanoHexano


Nomenclatura IUPAC de Alcanos Nomenclatura IUPAC de Alcanos Ramificados Ramificados

1) Selecciona la cadena de carbonos continua más 1) Selecciona la cadena de carbonos continua más larga y usar el nombre IUPAC del alcano larga y usar el nombre IUPAC del alcano no ramificado como base.no ramificado como base.

2) Identifica los grupos sustituyentes unidos a la 2) Identifica los grupos sustituyentes unidos a la cadena base.cadena base.

3) Enumera la cadena continua más larga en la 3) Enumera la cadena continua más larga en la dirección que da el número más bajo al dirección que da el número más bajo al grupo sustituyente en el primer punto de grupo sustituyente en el primer punto de ramificación.ramificación.

(CH(CH33))22CHCHCHCH22CHCH22CHCH33

(CH(CH33CHCH22))22CHCHCHCH33

2-Metilpentano2-Metilpentano

3-Metilpentano3-Metilpentano


(CH(CH33))22CHCH(CHCHCH(CH33))22

(CH(CH33))33CCHCCH22CHCH33

2,3-Dimetilbutano2,3-Dimetilbutano

2,2-Dimetilbutano2,2-Dimetilbutano

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


Grupos AlquiloGrupos Alquilo

Grupos Metilo y EtiloGrupos Metilo y Etilo

MetiloMetilo

EtiloEtilo CC CCHH

HH HH

HH HH

CHCH33CHCH22

CCHH

HH

HH

CHCH33oo

oo

Grupos Alquilo no RamificadosGrupos Alquilo no Ramificados

RRHHRR

Si el punto de unión está en un extremo de Si el punto de unión está en un extremo de la cadena, en la nomenclatura IUPAC, se la cadena, en la nomenclatura IUPAC, se nombra reemplazando la terminación –nombra reemplazando la terminación –anoano por -ipor -ilolo..

ButiloButilo

RRHHRR

CHCH33CHCH22CHCH22CHCH22CC CCHH

HH HH

HH HH

CC CC

HH HH

HH HH

oo


Si el punto de unión está en un extremo de la Si el punto de unión está en un extremo de la cadena, en la nomenclatura IUPAC, se nombra cadena, en la nomenclatura IUPAC, se nombra reemplazando la terminación –reemplazando la terminación –anoano por -i por -ilolo..

HexiloHexiloCHCH33(CH(CH22))44CHCH22

CHCH33(CH(CH22))55CHCH22

CHCH33(CH(CH22))1616CHCH22

HeptiloHeptilo

OctadeciloOctadecilo


Los Grupos Alquilo CLos Grupos Alquilo C33HH77

CHCH33CHCH22CHCH22CC CCHH

HH HH

HH HH

CC

HH

HH

oo

yy

CHCH33CHCHCHCH33CC CCHH

HH HH

HH

HHCC

HH

HH

oo


HH HH

HH HH

CC

HH

HH

oo

Nombre IUPAC: PropiloNombre IUPAC: Propilo

Nombre común : Nombre común : nn-Propilo-Propilo


Nombrando a los Grupos Alquilo Nombrando a los Grupos Alquilo

1: Identifica la cadena contínua más larga 1: Identifica la cadena contínua más larga comenzando en el punto de unión.comenzando en el punto de unión.

2: Drop -2: Drop -aneane ending from name of unbranched ending from name of unbranched alkane having same number of carbons as alkane having same number of carbons as longest continuous chain and replace by -longest continuous chain and replace by -ylyl..

3: Identifica los sustituyentes en la cadena 3: Identifica los sustituyentes en la cadena continua más larga.continua más larga.

4: La cadena siempre se numera comenzando en 4: La cadena siempre se numera comenzando en el punto de union.el punto de union.

Nombre IUPAC : 1-MetiletiloNombre IUPAC : 1-Metiletilo

Nombre común : IsopropiloNombre común : Isopropilo


HH HH

HH

CC

HH

HH

ooHH



HH HH

HH HH

CC

HH

HH

oror

Classification: Primary alkyl groupClassification: Primary alkyl group

Alkyl groups are classified according to theAlkyl groups are classified according to thedegree of substitution at the carbon that bears thedegree of substitution at the carbon that bears thepoint of attachment. A carbon that is directlypoint of attachment. A carbon that is directlyattached to one other carbon is a primary carbon.attached to one other carbon is a primary carbon.

The CThe C33HH77 Alkyl Groups Alkyl Groups

Classification: Secondary alkyl groupClassification: Secondary alkyl group

Alkyl groups are classified according to theAlkyl groups are classified according to thedegree of substitution at the carbon that bears thedegree of substitution at the carbon that bears thepoint of attachment. A carbon that is directlypoint of attachment. A carbon that is directlyattached to two other carbons is a secondary carbon.attached to two other carbons is a secondary carbon.


HH HH

HH

CC

HH

HH

ororHH


IUPAC name: ButylIUPAC name: Butyl

Common name: Common name: nn-Butyl-Butyl


CHCH33CHCH22CHCH22CHCH22CC CCHH

HH HH

HH HH

CC CC

HH HH

HH HH

oror


IUPAC name: 1-MethylpropylIUPAC name: 1-Methylpropyl

Common name: Common name: secsec-Butyl-Butyl

Classification: Secondary alkyl groupClassification: Secondary alkyl group

CHCH33CHCHCHCH22CHCH33CC CCHH

HH HH

HH

HHCC CC

HH HH

HH HH

oror11 22 33


IUPAC name: 2-MethylpropylIUPAC name: 2-Methylpropyl

Common name: IsobutylCommon name: Isobutyl


112233CC

HH

CHCH22

CHCH33

CHCH33


IUPAC name: 1,1-DimethylethylIUPAC name: 1,1-Dimethylethyl

Common name: Common name: terttert-Butyl-Butyl

Classification: Tertiary alkyl groupClassification: Tertiary alkyl group

11 22CC CHCH33

CHCH33

CHCH33


Nombres IUPAC de AlcanosNombres IUPAC de AlcanosAltamente RamificadosAltamente Ramificados

Branched alkanesBranched alkanes OctaneOctane

4-Ethyloctane4-Ethyloctane

Branched alkanesBranched alkanes

4-Ethyl-3-methyloctane4-Ethyl-3-methyloctane

List substituents in alphabetical order.List substituents in alphabetical order.


4-Ethyl-3,5-dimethyloctane4-Ethyl-3,5-dimethyloctane

List substituents in alphabetical order.List substituents in alphabetical order.But don't alphabetize di-, tri-, tetra-, etc.But don't alphabetize di-, tri-, tetra-, etc.


First Point of Difference RuleFirst Point of Difference Rule

The chain is numbered in the direction that The chain is numbered in the direction that gives the lower locant to the substituent at the gives the lower locant to the substituent at the first point of difference in the names.first point of difference in the names.

Don't add locants!Don't add locants!

2,2,6,6,7-Pentamethyloctane?2,2,6,6,7-Pentamethyloctane?


What is correct name?What is correct name?

1122 33

4455

6677

88

88

77 6655

4433

2211

First Point of Difference RuleFirst Point of Difference Rule

The chain is numbered in the direction that The chain is numbered in the direction that gives the lower locant to the substituent at the gives the lower locant to the substituent at the first point of difference in the names.first point of difference in the names.

Don't add locants!Don't add locants!


What is correct name?What is correct name?

88

77 6655

4433

2211

CCnnHH22nn

Nomenclatura de Nomenclatura de CicloalcanosCicloalcanos

CycloalkanesCycloalkanes

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

Count the number of carbons in the ring, and Count the number of carbons in the ring, and add the prefix add the prefix cyclocyclo to the IUPAC name of the to the IUPAC name of the unbranched alkane that has that number of unbranched alkane that has that number of carbons.carbons.

CyclopentaneCyclopentane CyclohexaneCyclohexane

EthylcyclopentaneEthylcyclopentane


CHCH22CHCH33

Name any alkyl groups on the ring in the usual Name any alkyl groups on the ring in the usual way.way.

Name any alkyl groups on the ring in the usual Name any alkyl groups on the ring in the usual way.way.

List substituents in alphabetical order and countList substituents in alphabetical order and countin the direction that gives the lowest numericalin the direction that gives the lowest numericallocant at the first point of difference.locant at the first point of difference.

3-Ethyl-1,1-dimethylcyclohexane3-Ethyl-1,1-dimethylcyclohexane

CHCH22CHCH33

HH33CC CHCH33


Nomenclatura de AlquenosNomenclatura de Alquenos

AlkenesAlkenes

Alkenes are hydrocarbons that contain a Alkenes are hydrocarbons that contain a carbon-carbon double bondcarbon-carbon double bond

also called "olefins"also called "olefins"

characterized by molecular formula Ccharacterized by molecular formula CnnHH2n2n

said to be "unsaturated"said to be "unsaturated"

HH22CC CHCH22 HH22CC CHCHCHCH33

EtheneEtheneoror

EthyleneEthylene(both are acceptable(both are acceptable

IUPAC names)IUPAC names)

PropenePropene

(Propylene is(Propylene issometimes used sometimes used

but is not an acceptablebut is not an acceptableIUPAC name)IUPAC name)

Alkene NomenclatureAlkene Nomenclature

1) Find the longest continuous chain that 1) Find the longest continuous chain that includes the double bond.includes the double bond.

2) Replace the -2) Replace the -aneane ending of the unbranched ending of the unbranched alkane having the same number of carbons alkane having the same number of carbons by -by -eneene..

3) Number the chain in the direction that gives 3) Number the chain in the direction that gives the lowest number to the doubly bonded the lowest number to the doubly bonded carbon.carbon.

HH22CC CHCHCHCH22CHCH33 1-Butene1-Butene


4) If a substituent is present, identify its position 4) If a substituent is present, identify its position by number. The double bond takes by number. The double bond takes precedence over alkyl groups and halogens precedence over alkyl groups and halogens when the chain is numbered.when the chain is numbered.

The compound shown above isThe compound shown above is4-bromo-3-methyl-1-butene.4-bromo-3-methyl-1-butene.

HH22CC CHCHCHCHCHCH22BrBr

CHCH33


4) If a substituent is present, identify its position 4) If a substituent is present, identify its position by number. by number. Hydroxyl groups take Hydroxyl groups take precedence over the double bond when the precedence over the double bond when the chain is numbered.chain is numbered.

The compound shown above isThe compound shown above is2-methyl-3-buten-1-ol.2-methyl-3-buten-1-ol.

HH22CC CHCHCHCHCHCH22OHOH

CHCH33


methylenemethylene

vinylvinyl

allylallyl

isopropenylisopropenyl

CHCHHH22CC

HH22CC CHCHCHCH22

HH22CC CCHCCH33

HH22CC

Alkenyl GroupsAlkenyl Groups

Cycloalkene NomenclatureCycloalkene Nomenclature

1) Replace the -1) Replace the -aneane ending of the cycloalkane ending of the cycloalkane having the same number of carbons by -having the same number of carbons by -eneene..

CyclohexeneCyclohexene

1) Replace the -1) Replace the -aneane ending of the cycloalkane ending of the cycloalkane having the same number of carbons by -having the same number of carbons by -eneene..

2) Number 2) Number throughthrough the double bond in the the double bond in thedirection that gives the lower number to the direction that gives the lower number to the first-appearing substituent.first-appearing substituent.

6-Ethyl-1-methylcyclohexene6-Ethyl-1-methylcyclohexeneCHCH33

CHCH22CHCH33

Cycloalkene NomenclatureCycloalkene Nomenclature

11

2233

44

55 66

AlquinosAlquinos

NomenclatureNomenclature

HCHC CHCHAcetylene and ethyne are both acceptableAcetylene and ethyne are both acceptableIUPAC names forIUPAC names for

Higher alkynes are named in much the sameHigher alkynes are named in much the sameway as alkenes except using an -way as alkenes except using an -yneyne suffix suffixinstead of -instead of -eneene..

HCHC CCHCCH33

PropynePropyne

HCHC CCHCCH22CHCH33

1-Butyne1-Butyne

(CH(CH33))33CCCC CCHCCH33

4,4-Dimethyl-2-pentyne4,4-Dimethyl-2-pentyne


Functional GroupsFunctional Groups

a structural unit in a molecule responsible for itsa structural unit in a molecule responsible for itscharacteristic behavior under a particular set ofcharacteristic behavior under a particular set ofreaction conditionsreaction conditions

Functional GroupFunctional Group

AlcoholAlcohol ROHROH

Alkyl halideAlkyl halide RRXX ( (XX = F, Cl, Br, I) = F, Cl, Br, I)

AmineAmine primary amine: Rprimary amine: RNHNH22

secondary amine: Rsecondary amine: R22NHNH

tertiary amine: Rtertiary amine: R33NN

Families of organic compoundsFamilies of organic compoundsand their functional groupsand their functional groups

EtherEther RROOR'R'

NitrileNitrile RRCNCN

NitroalkaneNitroalkane RRNONO22

SulfideSulfide RSR'RSR'

ThiolThiol RSHRSH

EpoxideEpoxide CC CC

OO

Families of organic compoundsFamilies of organic compoundsand their functional groupsand their functional groups

OO

CC

Carbonyl groupCarbonyl group

OO

CC

Acyl groupAcyl group

RR

Many classes of organic compounds contain Many classes of organic compounds contain a carbonyl groupa carbonyl group

OO

CC


OO

CC

AldehydeAldehyde

RR HH


OO

CC


OO

CC

KetoneKetone

RR R'R'


OO

CC


OO

CC

Carboxylic acidCarboxylic acid

RR OHOH


OO

CC


OO

CC

EsterEster

RR OR'OR'


OO

CC


OO

CC

AmideAmide

RR NHNH22


IUPAC NomenclatureIUPAC Nomenclature

of Alkyl Halidesof Alkyl Halides

The two that are most widely used are:The two that are most widely used are:functional class nomenclaturefunctional class nomenclaturesubstitutive nomenclaturesubstitutive nomenclature

Both types can be applied to alcohols andBoth types can be applied to alcohols andalkyl halides.alkyl halides.


There are several kinds of IUPAC nomenclature.There are several kinds of IUPAC nomenclature.

Name the alkyl group and the halogen asName the alkyl group and the halogen asseparate words (separate words (alkylalkyl + + halidehalide))

Functional Class Nomenclature of Alkyl HalidesFunctional Class Nomenclature of Alkyl Halides

CHCH33FF CHCH33CHCH22CHCH22CHCH22CHCH22ClCl

CHCH33CHCH22CHCHCHCH22CHCH22CHCH33

BrBr

HH

II

Name the alkyl group and the halogen asName the alkyl group and the halogen asseparate words (separate words (alkylalkyl + + halidehalide))

Functional Class Nomenclature of Alkyl HalidesFunctional Class Nomenclature of Alkyl Halides

CHCH33FF CHCH33CHCH22CHCH22CHCH22CHCH22ClCl

CHCH33CHCH22CHCHCHCH22CHCH22CHCH33

BrBr

Methyl fluorideMethyl fluoride Pentyl chloridePentyl chloride

1-Ethylbutyl bromide1-Ethylbutyl bromide Cyclohexyl iodideCyclohexyl iodide

HH

II

Name as halo-substituted alkanes.Name as halo-substituted alkanes.

Number the longest chain containing theNumber the longest chain containing thehalogen in the direction that gives the lowesthalogen in the direction that gives the lowestnumber to the substituted carbon.number to the substituted carbon.

Substitutive Nomenclature of Alkyl HalidesSubstitutive Nomenclature of Alkyl Halides

CHCH33CHCH22CHCH22CHCH22CHCH22FF CHCH33CHCHCHCH22CHCH22CHCH33

BrBr

CHCH33CHCH22CHCHCHCH22CHCH33

II

Name as halo-substituted alkanes.Name as halo-substituted alkanes.

Number the longest chain containing theNumber the longest chain containing thehalogen in the direction that gives the lowesthalogen in the direction that gives the lowestnumber to the substituted carbon.number to the substituted carbon.


CHCH33CHCH22CHCH22CHCH22CHCH22FF CHCH33CHCHCHCH22CHCH22CHCH33

BrBr1-Fluoropentane1-Fluoropentane

3-Iodopentane3-Iodopentane

2-Bromopentane2-BromopentaneCHCH33CHCH22CHCHCHCH22CHCH33

II


Halogen and alkyl groupsHalogen and alkyl groupsare of equal rank when are of equal rank when it comes to numberingit comes to numberingthe chain.the chain.

Number the chain in theNumber the chain in thedirection that gives the direction that gives the lowest number to thelowest number to thegroup (halogen or alkyl)group (halogen or alkyl)that appears first.that appears first.

CHCH33

ClCl ClCl

CHCH33


5-Chloro-2-methylheptane5-Chloro-2-methylheptane

2-Chloro-5-methylheptane2-Chloro-5-methylheptane

CHCH33

ClCl ClCl

CHCH33


of Alcoholsof Alcohols

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

Functional Class Nomenclature of AlcoholsFunctional Class Nomenclature of Alcohols

CHCH33CHCH22OHOH

CHCH33CHCHCHCH22CHCH22CHCH22CHCH33

OHOH

CHCH33CCHCCH22CHCH22CHCH33

OHOH

CHCH33

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

Functional Class Nomenclature of AlcoholsFunctional Class Nomenclature of Alcohols

CHCH33CHCH22OHOH


OHOH


OHOH

CHCH33

Ethyl alcoholEthyl alcohol

1-Methylpentyl alcohol1-Methylpentyl alcohol

1,1-Dimethylbutyl1,1-Dimethylbutylalcoholalcohol

Name as "alkanols." Replace -e ending of alkaneName as "alkanols." Replace -e ending of alkanename by -ol.name by -ol.

Number chain in direction that gives lowest numberNumber chain in direction that gives lowest numberto the carbon that bears the —OH group.to the carbon that bears the —OH group.

Substitutive Nomenclature of AlcoholsSubstitutive Nomenclature of Alcohols

CHCH33CHCH22OHOH


OHOH


OHOH

CHCH33

Name as "alkanols." Replace -e ending of alkaneName as "alkanols." Replace -e ending of alkanename by -ol.name by -ol.

Number chain in direction that gives lowest numberNumber chain in direction that gives lowest numberto the carbon that bears the —OH group.to the carbon that bears the —OH group.


CHCH33CHCH22OHOH


OHOH


OHOH

CHCH33

EthanolEthanol

2-Hexanol2-Hexanol

2-Methyl-2-pentanol2-Methyl-2-pentanol

OHOH

CHCH33


Hydroxyl groups outrank Hydroxyl groups outrank alkyl groups when alkyl groups when it comes to numberingit comes to numberingthe chain.the chain.

Number the chain in theNumber the chain in thedirection that gives the direction that gives the lowest number to thelowest number to thecarbon that bears thecarbon that bears theOH groupOH group

CHCH33

OHOH


6-Methyl-3-heptanol6-Methyl-3-heptanol

5-Methyl-2-heptanol5-Methyl-2-heptanol

OHOH

CHCH33

CHCH33

OHOH

Classes of AlcoholsClasses of Alcohols

and Alkyl Halidesand Alkyl Halides

Alcohols and alkyl halides are classified asAlcohols and alkyl halides are classified asprimaryprimarysecondarysecondarytertiarytertiary

according to their "degree of substitution."according to their "degree of substitution."

Degree of substitution is determined by countingDegree of substitution is determined by countingthe number of carbon atoms directly attached tothe number of carbon atoms directly attached tothe carbon that bears the halogen or hydroxyl group.the carbon that bears the halogen or hydroxyl group.

ClassificationClassification

CHCH33CHCH22CHCH22CHCH22CCHH22FF

CHCH33CCHCHHCH22CHCH22CHCH33

BrBr

primary alkyl halideprimary alkyl halide

secondary alkyl halidesecondary alkyl halide

ClassificationClassification

CHCH33CCCHCH22CHCH22CHCH33

OHOH

CHCH33

tertiary alcoholtertiary alcohol

HH

OHOH

secondary alcoholsecondary alcohol

Ethers, Epoxides, and Sulfides

Nomenclature of Ethers, Epoxides, and Sulfides

name as alkoxy derivatives of alkanesname as alkoxy derivatives of alkanes

CHCH33OOCHCH2 2 CHCH33

methoxymethoxyethaneethane

CHCH33CHCH22OOCHCH2 2 CHCH33

ethoxyethoxyethaneethane

CHCH33CHCH22OOCHCH22CHCH22CHCH22ClCl

1-chloro-3-1-chloro-3-ethoxyethoxypropanepropane

Substitutive IUPAC Names of EthersSubstitutive IUPAC Names of Ethers

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

CHCH33OOCHCH2 2 CHCH33

ethylethyl methylmethyl ether ether

CHCH33CHCH22OOCHCH2 2 CHCH33

didiethylethyl ether ether

CHCH33CHCH22OOCHCH22CHCH22CHCH22ClCl

3-chloropropyl3-chloropropyl ethylethyl ether ether

Functional Class IUPAC Names of EthersFunctional Class IUPAC Names of Ethers

name as alkylthio derivatives of alkanesname as alkylthio derivatives of alkanes

CHCH33SSCHCH2 2 CHCH33

methylthiomethylthioethaneethane

CHCH33CHCH22SSCHCH2 2 CHCH33

ethylthioethylthioethaneethane

(methylthio)cyclopentane(methylthio)cyclopentane

Substitutive IUPAC Names of SulfidesSubstitutive IUPAC Names of Sulfides

SCHSCH33

cyclopentyl cyclopentyl methylmethyl sulfide sulfide

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

CHCH33SSCHCH2 2 CHCH33

ethylethyl methyl sulfide methyl sulfide

CHCH33CHCH22SSCHCH2 2 CHCH33

didiethylethyl sulfide sulfide

Functional Class IUPAC Names of SulfidesFunctional Class IUPAC Names of Sulfides

SSCHCH33

OxiraneOxirane(Ethylene oxide)(Ethylene oxide)

OxetaneOxetane OxolaneOxolane(tetrahydrofuran)(tetrahydrofuran)

OxaneOxane(tetrahydropyran)(tetrahydropyran)

1,4-Dioxane1,4-Dioxane

Names of Cyclic EthersNames of Cyclic Ethers OO OO OO

OO

OO

OO

ThiiraneThiirane ThietaneThietane ThiolaneThiolane

ThianeThiane

Names of Cyclic SulfidesNames of Cyclic Sulfides SS SS SS

SS

AminesAmines

Amine NomenclatureAmine Nomenclature

AlkylamineAlkylamine

N attached to alkyl groupN attached to alkyl group

ArylamineArylamine

N attached to aryl groupN attached to aryl group

Primary, secondary, or tertiaryPrimary, secondary, or tertiary

determined by number of carbon atoms determined by number of carbon atoms directly attached to nitrogendirectly attached to nitrogen

Classification of AminesClassification of Amines

Two IUPAC stylesTwo IUPAC styles

1)1) analogous to alcohols: replace -analogous to alcohols: replace -e e ending by -ending by -anamineanamine

2)2) name alkyl group and attach -name alkyl group and attach -amineamineas a suffixas a suffix

Nomenclature of Primary Alkylamines (RNHNomenclature of Primary Alkylamines (RNH22))

Examples: some primary alkylaminesExamples: some primary alkylamines

CHCH33CHCHCHCH22CHCH22CHCH33

NNHH22

(RNH(RNH22: one carbon directly attached to N): one carbon directly attached to N)

CHCH33CHCH22NNHH22 NNHH22

ethylamineethylamine or or ethanamineethanamine

cyclohexylaminecyclohexylamine or orcyclohexanaminecyclohexanamine

1-methylbutylamine 1-methylbutylamine oror2-pentanamine2-pentanamine

Name as derivatives of aniline.Name as derivatives of aniline.

Nomenclature of Primary Arylamines (ArNHNomenclature of Primary Arylamines (ArNH22))

pp-fluoroaniline-fluoroaniline 5-bromo-2-ethylaniline5-bromo-2-ethylaniline

NNHH22FF

NNHH22

BrBr CHCH22CHCH33

Amino groups as substituentsAmino groups as substituents

pp-aminobenzaldehyde-aminobenzaldehyde

amino groups rank below OH groups and higher amino groups rank below OH groups and higher oxidation states of carbonoxidation states of carbon

in such cases name the amino group as a in such cases name the amino group as a substituentsubstituent

NNHH22HHCC

OO

HHOOCHCH22CHCH22NNHH22

2-aminoethanol2-aminoethanol

Name as Name as NN-substituted derivatives of parent -substituted derivatives of parent primary amine.primary amine.

(N is a locant-it is not alphabetized, but(N is a locant-it is not alphabetized, butis treated the same way as a numericalis treated the same way as a numericallocant)locant)

Parent amine is one with longest carbonParent amine is one with longest carbonchain.chain.

Secondary and Tertiary AminesSecondary and Tertiary Amines

ExamplesExamples

CHCH33NNHCHHCH22CHCH33 NN-methylethylamine-methylethylamine NNHCHHCH22CHCH33

NONO22

ClCl

4-chloro-4-chloro-NN-ethyl-3-nitroaniline-ethyl-3-nitroaniline

CHCH33

NN

CHCH33

NN,,NN-dimethylcycloheptylamine-dimethylcycloheptylamine

A nitrogen with four substituents is positivelyA nitrogen with four substituents is positivelycharged and is named as a derivative of charged and is named as a derivative of ammonium ammonium ion (NHion (NH44

++).).

Ammonium SaltsAmmonium Salts

CHCH33NHNH33

++ClCl

––

methylammoniummethylammonium

chloridechloride

NN

CHCH33

HH

CHCH22CHCH33

++CFCF33COCO22

––

NN-ethyl--ethyl-NN-methylcyclopentylammonium-methylcyclopentylammonium

trifluoroacetatetrifluoroacetate

When all four atoms attached to N are carbon,When all four atoms attached to N are carbon,the ion is called a the ion is called a quaternary ammonium quaternary ammonium ion andion andsalts that contain it are called salts that contain it are called quaternaryquaternary ammoniumammonium salts. salts.

Ammonium SaltsAmmonium Salts

++

CHCH22 NN

CHCH33

CHCH33

CHCH33 II––

benzyltrimethylammonium iodidebenzyltrimethylammonium iodide

IUPAC Nomenclature of AldehydesIUPAC Nomenclature of Aldehydes HH

OO OO

HH

OO HCCHCHHCCHCH

OOBase the name on the Base the name on the chain that contains chain that contains the carbonyl group the carbonyl group and replace the and replace the -e-e ending of the ending of the hydrocarbon by hydrocarbon by -al-al..

4,4-dimethylpent4,4-dimethylpentananalal 5-hex5-hexenenalal

IUPAC Nomenclature of AldehydesIUPAC Nomenclature of Aldehydes HH

OO OO

HH

OO HCCHCHHCCHCH

OO

2-phenylprop2-phenylpropaneanedialdial(keep the (keep the -e -e endingendingbefore before -dial-dial))

when named as when named as a substituenta substituent

formyl groupformyl group carbaldehyde orcarbaldehyde orcarboxaldehydecarboxaldehyde

when named when named as a suffixas a suffix

CC HH

OO

IUPAC Nomenclature of Aldehydes IUPAC Nomenclature of Aldehydes

CHCH33CHCH22CCHCCH22CHCH22CHCH33

OO

CHCH33CHCHCHCH22CCHCCH33

OO

CHCH33 HH33CC OO

Base the name on the chain Base the name on the chain that contains the carbonyl that contains the carbonyl group and replace group and replace -e-e by by -one-one. . Number the chain in the Number the chain in the direction that gives the lowest direction that gives the lowest number to the carbonyl number to the carbonyl carbon.carbon.

Substitutive IUPAC Nomenclature of KetonesSubstitutive IUPAC Nomenclature of Ketones

Substitutive IUPAC Nomenclature of KetonesSubstitutive IUPAC Nomenclature of Ketones

CHCH33CHCH22CCHCCH22CHCH22CHCH33

OO

CHCH33CHCHCHCH22CCHCCH33

OO

CHCH33 HH33CC OO

3-3-hexanhexanoneone

4-methyl4-methyl-2--2-pentanpentanoneone

4-methylcyclohexan4-methylcyclohexanoneone

Functional Class IUPAC Nomenclature of KetonesFunctional Class IUPAC Nomenclature of Ketones

CHCH33CHCH22CCCHCH22CHCH22CHCH33

OO OO

CHCH22CCCHCH22CHCH33

CHCH CHCH22

OO

HH22CC CHCCHC

List the groups List the groups attached to the attached to the carbonyl separately in carbonyl separately in alphabetical order, and alphabetical order, and add the word add the word ketoneketone..

CHCH33CHCH22CCCHCH22CHCH22CHCH33

OO

ethylethyl propylpropyl ketone ketone benzylbenzyl ethylethyl ketone ketone

divinyl ketonedivinyl ketone

OO

CHCH22CCCHCH22CHCH33

CHCH CHCH22

OO

HH22CC CHCCHC

Functional Class IUPAC Nomenclature of KetonesFunctional Class IUPAC Nomenclature of Ketones

Carboxylic AcidsCarboxylic Acids

Carboxylic Acid Carboxylic Acid NomenclatureNomenclature

Systematic NameSystematic NameOO

HCOHHCOH

OO

CHCH33COHCOH

OO

CHCH33(CH(CH22))1616COHCOH

methanoic acidmethanoic acid

ethanoic acidethanoic acid

octadecanoic acidoctadecanoic acid

systematic IUPAC names replace "-e" systematic IUPAC names replace "-e" ending of alkane with "oic acid"ending of alkane with "oic acid"

Systematic NameSystematic Name Common NameCommon NameOO

HCOHHCOH methanoic acidmethanoic acid formic acidformic acid

OO

CHCH33COHCOH ethanoic acidethanoic acid acetic acidacetic acid

OO

CHCH33(CH(CH22))1616COHCOH octadecanoic acidoctadecanoic acid stearic acidstearic acid

common names are based on natural origin common names are based on natural origin rather than structurerather than structure

Systematic NameSystematic Name Common NameCommon Name

2-hydroxypropanoic2-hydroxypropanoicacidacid

lactic acidlactic acid

((ZZ)-9-octadecenoic)-9-octadecenoicacidacid

oleic acidoleic acid

OO

CHCH33CHCOHCHCOH

OHOH OO

(CH(CH22))77COHCOH

CC CC

HH HH

CHCH33(CH(CH22))77

Nomenclature of Carboxylic Acid DerivativesNomenclature of Carboxylic Acid Derivatives

Acyl HalidesAcyl Halides

RCRC

OO

XX

name the acyl group and add the word name the acyl group and add the word chloridechloride, , fluoridefluoride, , bromidebromide, or , or iodideiodide

as appropriateas appropriate

acyl chlorides are, by far, the most frequently encountered of the acyl halidesacyl chlorides are, by far, the most frequently encountered of the acyl halides

Acyl HalidesAcyl Halides

CHCH33CCClCl

OO

acetyl acetyl chloridechloride

3-butenoyl 3-butenoyl chloridechloride

OO

HH22CC CHCHCHCH22CCClCl OO

CCBrBrFF pp-fluorobenzoyl -fluorobenzoyl bromidebromide

Acid AnhydridesAcid Anhydrides

when both acyl groups are the same, name the when both acyl groups are the same, name the

acid and add the word acid and add the word anhydrideanhydride

when the groups are different, list the names of the when the groups are different, list the names of the

corresponding acids in alphabetical order and add corresponding acids in alphabetical order and add

the word the word anhydrideanhydride

RCRCOOCR'CR'

OO OO

Acid AnhydridesAcid Anhydrides

acetic anhydrideacetic anhydride

benzoic anhydridebenzoic anhydride

benzoicbenzoic heptanoicheptanoic anhydride anhydride

CHCH33CCOOCCHCCH33

OO OO

CC66HH55CCOOCCCC66HH55

OO OO

CC66HH55CCOOC(CHC(CH22))55CHCH33

OO OO

EstersEsters

name as name as alkylalkyl alkanoatesalkanoates

cite the alkyl group attached to oxygen first (R')cite the alkyl group attached to oxygen first (R')

name the acyl group second; substitute the suffixname the acyl group second; substitute the suffix

-ate-ate for the for the -ic -ic ending of the corresponding acidending of the corresponding acid

RCRCOOR'R'

OO

EstersEsters

CHCH33CCOOCHCH22CHCH33

OO

ethylethyl acetate acetate

methylmethyl propanoate propanoate

2-chloroethyl2-chloroethyl benzoate benzoate

OO

CHCH33CHCH22CCOOCHCH33

CCOOCHCH22CHCH22ClCl

OO

Amides having an NHAmides having an NH22 group group

identify the corresponding carboxylic acididentify the corresponding carboxylic acid

replace the replace the -ic acid -ic acid or or -oic acid -oic acid ending by -amideending by -amide

RCRCNNHH22

OO

Amides having an NHAmides having an NH22 group group

CHCH33CCNNHH22

OO

acetacetamideamide

3-methylbutan3-methylbutanamideamide

OO

(CH(CH33))22CHCHCHCH22CCNNHH22

CCNNHH22

OO benzbenzamideamide

Amides having substituents on NAmides having substituents on N

name the amide as beforename the amide as before

precede the name of the amide with the name of precede the name of the amide with the name of

the appropriate group or groupsthe appropriate group or groups

precede the names of the groups by the letter precede the names of the groups by the letter N- N-

(standing for nitrogen and used as a locant)(standing for nitrogen and used as a locant)

RCRCNNHHR'R'

OO

andand RCRCNNR'R'22

OO

Amides having substituents on NAmides having substituents on N

CHCH33CCNNHHCHCH33

OO

NN--methylmethylacetamideacetamide

NN--isopropylisopropyl--NN--methylmethylbutanamidebutanamide

CCNN(CH(CH22CHCH33))22

OO NN,,NN--diethyldiethylbenzamidebenzamide

OO

CHCH33CHCH22CHCH22CCNNCH(CHCH(CH33))22

CHCH33

NitrilesNitriles

add the suffix add the suffix -nitrile -nitrile to the name of the parent to the name of the parent

hydrocarbon chain (including the triply bonded hydrocarbon chain (including the triply bonded

carbon of CN)carbon of CN)

or: replace the or: replace the -ic acid -ic acid or or -oic acid -oic acid name of the name of the

corresponding carboxylic acid by corresponding carboxylic acid by -onitrile-onitrile

or: name as an or: name as an alkyl cyanide alkyl cyanide (functional class (functional class

name)name)

RCRC NN

NitrilesNitriles

CHCH33CC NNethanenitrileethanenitrileor: acetonitrileor: acetonitrileor: methyl cyanideor: methyl cyanide

CC66HH55CC NN benzonitrilebenzonitrile

NNCC

CHCH33CHCHCHCH33 2-methylpropanenitrile2-methylpropanenitrileor: isopropyl cyanideor: isopropyl cyanide

nomenclatura

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