An Introduction to Organic Compounds: Chapter 2Contents of Chapter 2Counting to Ten in OrganicAlkanesPrimary, Secondary, TertiaryNomenclature of Alkyl SubstituentsSlide 7Slide 8IUPAC Systematic Nomenclature - AlkanesSlide 10Slide 11Slide 12Slide 13Slide 14Nomenclature of CycloalkanesSlide 16Slide 17Slide 18Nomenclature of Alkyl HalidesSlide 20Nomenclature of EthersSlide 22Nomenclature of AlcoholsSlide 24IUPAC Nomenclature of AlcoholsSlide 26Slide 27Nomenclature of AminesSlide 29IUPAC Nomenclature of AminesProperties of Alkyl Halides, Alcohols, Ethers, & AminesInduced Dipole-Induced Dipole InteractionsHydrogen Bonding: Strong Dipole-Dipole InteractionsDipole-dipole InteractionsComparative Boiling PointsSolubilityNewman ProjectionsConformations of Alkanes: Rotation About C-C Single BondsChair Conformation of CyclohexaneDrawing Cyclohexane in the Chair ConformationInterconversion of Cyclohexane ConformationsMonosubstituted CyclohexanesConformations of 1,4-Disubstituted CyclohexanesSlide 44Slide 45Conformations of cis-1,3-Disubstituted CyclohexanesConformations of trans-1,3-Disubstituted CyclohexanesChapter 2 1An Introduction to Organic An Introduction to Organic Compounds:Compounds:Chapter 2Chapter 2Nomenclature, Physical Properties, and Nomenclature, Physical Properties, and Representation of StructureRepresentation of StructureChapter 2 2Contents of Chapter 2NomenclatureStructures of Alkyl Halides, Alcohols, Ethers, and AminesPhysical PropertiesConformations of AlkanesCycloalkanesChapter 2 3Counting to Ten in Organic01 = meth Mother02 = eth Enjoys03 = prop Peanut04 = but BUTter05 = pent PENTagon06 = hex HEXagon or HEX nut07 = hept HEPTember (Roman sept is Greek hept)08 = oct OCTober09 = non NONember (Roman nov is Greek non)10 = dec DECemberChapter 2 4AlkanesChapter 2 5Primary, Secondary, TertiaryA primary carbon has one other C directly bonded to it.A secondary carbon is directly bonded to two other C’s.A tertiary carbon is directly bonded to three other C’s.Multivalent atoms are 1º, 2º, or 3º by bonding to C’s.Univalent atom or group not really 1º, 2º, or 3º on its own - ID depends on type of carbon it is bonded to.Chapter 2 6Nomenclature of Alkyl SubstituentsThere are four alkyl groups that contain four carbonsChapter 2 7Nomenclature of Alkyl SubstituentsThe prefix sec- occurs only in sec-butylChapter 2 8Nomenclature of Alkyl SubstituentsThe prefix tert- can be used with butyl or pentyl (also known as amyl) but not with hexylChapter 2 9IUPAC Systematic Nomenclature - Alkanes•Determine longest continuous chain (i.e. parent hydrocarbon)•Cite the name of substituent before the name of the parent hydrocarbon along with the number of the carbon to which it is attachedChapter 2 10IUPAC Systematic Nomenclature - Alkanes•Number in the direction that gives the lower number for the lowest-numbered substituent. Substituents are listed in alphabetical order – neglecting prefixes such as di- tri- tert- etc.Chapter 2 11IUPAC Systematic Nomenclature - Alkanes•When both directions yield the same lower number for the lowest numbered substituent, select the direction that yields the lower number for the next lowest numbered substituentChapter 2 12IUPAC Systematic Nomenclature - Alkanes•If same substituent numbers are obtained in either direction, number in direction giving lowest number to the first named substituentChapter 2 13IUPAC Systematic Nomenclature - Alkanes•If compound has two or more chains of the same length, parent hydrocarbon is chain with greatest number of substituentsChapter 2 14IUPAC Systematic Nomenclature - Alkanes•Names such as sec-butyl and tert-butyl are acceptable, but systematic substituent names are preferable•Numbering of the substituent begins with the carbon attached to the parent hydrocarbon•This number together with the substituent name is placed inside parenthesesChapter 2 15Nomenclature of CycloalkanesCycloalkanes generally are shown as skeletal structuresChapter 2 16Nomenclature of Cycloalkanes•Ring is the parent hydrocarbon unless the alkyl substituent has more carbons; in that case the substituent becomes the parent hydrocarbon•If only one substituent, no need to give it a numberChapter 2 17Nomenclature of Cycloalkanes•If the ring has 2 substituents, list in alphabetical order and give number 1 to first named groupChapter 2 18Nomenclature of Cycloalkanes•If there is more than one substituent, list in alphabetical order; one substituent is given the position number 1; number either clockwise or counterclockwise - lowest numbersChapter 2 19Nomenclature of Alkyl HalidesCommon name - Name the alkyl group first, followed by the name of the halogen expressed as an -ide nameChapter 2 20Nomenclature of Alkyl HalidesIUPAC name - The halogen is treated as a substituentChapter 2 21Nomenclature of EthersCommon name - Name(s) of alkyl group(s) listed first followed by the word “ether”Chapter 2 22Nomenclature of EthersIUPAC name - The smaller alkyl group is converted to an “alkoxy” name and used as a substituentChapter 2 23Nomenclature of AlcoholsCommon name - Name of the Alkyl group followed by the word “alcohol”Chapter 2 24Nomenclature of AlcoholsIUPAC name - The OH group is a site of reactivity (a functional group)Functional group is denoted by the suffix, “ol”CH3OH CH3CH2OHmethanol ethanolChapter 2 25IUPAC Nomenclature of Alcohols•Parent Hydrocarbon is the longest continuous chain that contains the OH•Number the chain in direction that gives functional group the lowest number•If both a substituent and a functional group are present, the functional group gets the lower numberChapter 2 26IUPAC Nomenclature of Alcohols•If the functional group gets the same number when counted from both directions, use direction which gives the substituent the lower number•If there is more than one substituent, cite substituents in alphabetical orderChapter 2 27IUPAC Nomenclature of AlcoholsSystem is summarized as [Substituent] [Parent Hydrocarbon] [Functional Group]Chapter 2 28Nomenclature of AminesCommon name - Name of the Alkyl group(s) (in alphabetical order) followed by the syllable “amine”The whole name is a single wordmethylamine methylpropylamineChapter 2 29Nomenclature of AminesIUPAC name - The NH2 group is a site of reactivity (a functional group)Functional group is denoted