IUPAC Nomenclature of Unbranched Alkanes. Retained: methaneCH 4 ethaneCH 3 CH 3 propaneCH 3 CH 2 CH 3 butaneCH 3 CH 2 CH 2 CH 3 IUPAC Names of Unbranched

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Text of IUPAC Nomenclature of Unbranched Alkanes. Retained: methaneCH 4 ethaneCH 3 CH 3 propaneCH 3 CH 2 CH...

  • IUPAC Nomenclature ofUnbranched Alkanes

  • IUPAC Names of Unbranched AlkanesRetained:methaneCH4ethaneCH3CH3propaneCH3CH2CH3butaneCH3CH2CH2CH3

  • IUPAC Names of Unbranched AlkanesNote: n-prefix is not part of IUPAC name of any alkane.For example: n-butane is "common name" for CH3CH2CH2CH3; butane is "IUPAC name."Others:Latin or Greek prefix for number of carbons + ane suffix

  • IUPAC Names of Unbranched AlkanesNumber of carbons NameStructure5pentaneCH3(CH2)3CH36hexaneCH3(CH2)4CH37heptaneCH3(CH2)5CH38octaneCH3(CH2)6CH39nonaneCH3(CH2)7CH310decaneCH3(CH2)8CH3

  • IUPAC Names of Unbranched AlkanesNumber of carbons NameStructure11undecaneCH3(CH2)9CH312dodecaneCH3(CH2)10CH313tridecaneCH3(CH2)11CH314tetradecaneCH3(CH2)12CH315pentadecaneCH3(CH2)7CH316hexadecaneCH3(CH2)8CH3

  • IUPAC Names of Unbranched AlkanesNumber of carbons NameStructure17heptadecaneCH3(CH2)15CH318octadecaneCH3(CH2)16CH319nonadecaneCH3(CH2)17CH320icosaneCH3(CH2)18CH325pentacosaneCH3(CH2)22CH330triacontaneCH3(CH2)28CH3

  • Applying the IUPAC Rules:The Names of the C6H14 Isomers

  • The C6H14 IsomersCH3CH2CH2CH2CH2CH3(CH3)2CHCH2CH2CH3(CH3CH2)2CHCH3(CH3)2CHCH(CH3)2(CH3)3CCH2CH3

  • The C6H14 IsomersThe IUPAC name of the unbranched alkane with a chain of 6 carbons is hexane.CH3CH2CH2CH2CH2CH3Hexane

  • IUPAC Nomenclature of Branched

    Step 1) Find the longest continuous carbon chain and use the IUPAC name of the unbranched alkane as the basis.Step 2) Add name of substituent as a prefix.Step 3) Number the chain from the end nearest the substituent, and identify the carbon to which the substituent is attached by number.

  • The C6H14 Isomers(CH3)2CHCH2CH2CH3(CH3CH2)2CHCH32-Methylpentane3-Methylpentane

  • The C6H14 IsomersUse replicating prefixes (di-, tri-, tetra-, etc.) according to the number of identical substituents attached to the main chain.(CH3)2CHCH(CH3)2(CH3)3CCH2CH32,3-Dimethylbutane2,2-Dimethylbutane

  • Alkyl Groups

  • Methyl and Ethyl GroupsMethylEthyloror

  • Unbranched Alkyl GroupsIf potential point of attachment is at the end of the chain, take the IUPAC name of the corresponding unbranched alkane and replace the -ane ending by -yl.

  • Unbranched Alkyl GroupsIf potential point of attachment is at the end of the chain, take the IUPAC name of the corresponding unbranched alkane and replace the -ane ending by -yl.Butylor

  • Unbranched Alkyl GroupsHexylHeptylOctadecyl

  • The C3H7 Alkyl GroupsCH3CH2CH2CCHHHHHCHHorandCH3CHCH3CCHHHHHCHHor

  • The C3H7 Alkyl GroupsIUPAC name: PropylCommon name: n-PropylCH3CH2CH2CCHHHHHCHHor

  • Step 1:Identify longest continuous chain starting at point of attachment.Step 2: Drop -ane ending from name of unbranched alkane having same number of carbons as longest continuous chain and replace by -yl.Step 3:Identify substituents on longest continuous chain.Step 4:Chain is always numbered starting at point of attachment.Naming Alkyl Groups (Table 2.8)

  • The C3H7 Alkyl GroupsIUPAC name: 1-MethylethylCommon name: Isopropyl

  • The C3H7 Alkyl GroupsClassification: Primary alkyl groupAlkyl 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 C3H7 Alkyl GroupsClassification: Secondary alkyl groupAlkyl 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 C4H9 Alkyl GroupsIUPAC name: ButylCommon name: n-ButylClassification: Primary alkyl group

  • The C4H9 Alkyl GroupsIUPAC name: 1-MethylpropylCommon name: sec-ButylClassification: Secondary alkyl groupCH3CHCH2CH3CCHHHHHCCHHHHor

  • The C4H9 Alkyl GroupsIUPAC name: 2-MethylpropylCommon name: IsobutylClassification: Primary alkyl group

  • The C4H9 Alkyl GroupsIUPAC name: 1,1-DimethylethylCommon name: tert-ButylClassification: Tertiary alkyl group12CCH3CH3CH3

  • IUPAC Names of HighlyBranched Alkanes

  • Branched alkanesOctane

  • Branched alkanes4-Ethyloctane

  • Branched alkanes4-Ethyl-3-methyloctaneList substituents in alphabetical order.

  • Branched alkanes4-Ethyl-3,5-dimethyloctaneList substituents in alphabetical order.But don't alphabetize di-, tri-, tetra-, etc.

  • First Point of Difference RuleThe 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?1234567887654321

  • First Point of Difference RuleThe 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?87654321

  • Cycloalkane NomenclatureCnH2n

  • CycloalkanesCycloalkanes 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.CyclopentaneCyclohexane

  • CycloalkanesName any alkyl groups on the ring in the usual way.Ethylcyclopentane

  • CycloalkanesName 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.3-Ethyl-1,1-dimethylcyclohexane

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