Chapter 2. Skeletal Structures

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1 Chapter 2 Basic nomenclature/definition of alkanes Nomenclature of alkyl groups Nomenclature of more complicated alkanes Nomenclature & structure of alkane derivatives: Alkyl halides Ethers Alcohols Amines Physical properties of alkanes & derivatives Conformations of alkanes Conformations of cycloalkanes Basic nomenclature/definition of alkanes Alkanes are hydrocarbons containing only single bonds General formula: C n H 2n+2 Skeletal Structures = H 3 C H 2 C = propane = H 3 C H 2 C H 2 C C H 2 H 2 C C H 2 C H 2 = octane

2 Constitutional isomers have the same molecular formula, but their atoms are linked differently Nomenclature of Alkyl Groups (or substituents )

3 A compound can have more than one name, but a name must specify only one compound A C 7 H 16 compound can be any one of the following: Nomenclature of more complicated alkanes 1. Determine the number of carbons in the parent hydrocarbon CH 2CH 2CH 2CHCH 2CH CH 2CH 2CH 2CHCH 2 CH 2CH CH 2CH 2CHCH 2CH 2 CH 2CH 2CH Number the chain so that the substituent gets the lowest possible number CHCH 2CH 2 2-methylpentane CH 2CH 2CHCH 2CH 2CH 2 CH 4-isopropyloctane CHCH 2CH 2 common name: isohexane systematic name: 2-methylpentane 3. Number the substituents to yield the lowest possible numbers in the name of the compound CH 2CHCH 2CHCH 2CH 2 CH 2 5-ehtyl-3-methyloctane 4-ethyl-6-methyloctane because 3<4 (substituents are listed in alphabetical order) CH 2CHCH 2CH 2,4-dimethylhexane CH 2CH 2C CCH 2 3,3,4,4-tetramethylheptane CH 2 CH 2CHCH 2CH 2CHCHCH 2CH 2 CH 2 CH 2 3,3,6-triethyl-7-methyldecane

4 4. When both directions lead to the same lowest number for one of the substituents, the direction is chosen that gives the lowest possible number to one of the remaining substituents CHCH 2CH 2,2,4-trimethylpentane 2,4,4-trimethylpentane because 2<4 CH 2CHCHCH 2CHCH 2 CH 2 6-ethyl-3,4-dimethyloctane 3-ethyl-5,6-dimethyloctane because 4<5 5. If the same number is obtained in both directions, the first group (alphaetically) receives the lowest number Cl CH 2CH Br 2-bromo-3-chlorobutane 3-bromo-2-chlorobutane CH 2 CH 2CHCH 2CHCH 2 3-ethyl-5-methylheptane 5-ethyl-3-methylheptane 6. In the case of two chains with the same number of carbons, the parent hydrocarbon is the one with the most substituents CH 2CHCH 2CH 2 2 CH 1 3-ethyl-2-methylhexane (two substituents) CH 2CHCH 2CH 2 CH 3-isopropylhexane (one substituent) 7. Certain common nomenclatures are used in the IUPAC system CH 2CH 2CH 2CHCH 2CH 2 CH 4-isopropyloctane or 4-(1-methylethyl)octane CH 2CH 2CH 2CHCH 2CH 2CH 2CH 2 CH 2CH 5-isobutyldecane or 5-(2-methylpropyl)decane Different Kinds of Carbons and Hydrogens

5 Nomenclature of Cycloalkanes 1. No number is needed for a single substituent on a ring CH 2 CH 2CH 2CH 2CH 2 methylcyclopentane ethylcyclohexane 1-cyclobutylpentane 2. Name the two substituents in alphabetical order H 3C CH 2CH 2 1-methyl-2-propylcyclopentane H 3CH 2C 1-ethyl-3-methylcyclopentane 1,3-dimethylcyclohexane 3. If there are more than two substituents, go for the lowest numbers CH 2CH 2 H 3C CH 2 4-ethyl-2-methyl-1-propylcyclohexane 1-ethyl-3-methyl-4-propylcyclohexane because2<3 5-ethyl-1-methyl-2-propylcyclohexane because 4<5 1,1,2-trimethylcyclopentane 1,2,2-trimethylcyclopentane because1<2 1,1,5-trimethylcyclopentane because 2<5 Nomenclature of Alkyl Halides CHI CH 2CHB r Cl CH 2F chloromethane fluoroethane 2-iodopropane 2-bromobutane In the IUPAC system, alkyl halides are named as substituted alkanes CH 2CHCH 2CH 2CH 2 Br 2-bromo-5-methylheptane Br CH 2CHCH 2CH 2CH 2Cl 1-chloro-5,5-dimethylhexane I CH 2 1-ethyl-2-iodocyclopentane Cl 4-bromo-2-chloro-1-methylcyclohexane

6 Different Kinds of Alkyl Halides Nomenclature of Ethers CH OCH 2 CH 2CHOC 3CH 2OCH 2 ethyl methyl ether diethyl ether tert-butyl isobutyl ether Small ethers are usually named by their common names, given above The IUPAC names for these ethers are Methoxyethane ethoxyethane 1-tert-butoxy-2-methylpropane As substituents: O methoxy CH 2O ethoxy CH 2O isopropoxy CH 2CHO sec-butoxy CH 2O tert-butoxy Nomenclature of Alcohols In an alcohol, the OH is a functional group A functional group is the center of reactivity in a molecule 1. Determine the parent hydrocarbon containing the functional group CHCH 2 OH 2-butanol or butan-2-ol CH 2CH 2CHCH 2OH CH 2 2-ethyl-1-pentanol or 2-ethylpentan-1-ol CH 2CH 2CH 2OCH 2CH 2CH 2OH 3-butoxy-1-propanol or 3-butoxypropan-1-ol

7 2. The functional group suffix should get the lowest number possible HO C H 2CH 2 1-propanol CH 2CH OH 2-butanol CCH 2CH OH 4,4-dimethyl-2-pentanol 3. When there is both a functional group suffix and a substituent, the functional group suffix gets the lowest number and the substituent gets the lowest possible number after that CHCHCH 2 Cl OH 2-chloro-3-pentanol 4-chloro-3-pentanol CH 2CH 2CHCH 2CH OH 2-methyl-4-heptanol 6-methyl-4-heptanol OH 3-methylcyclohexanol 5-methylcyclohexanol 4. If there is more than one substituent, the substituents are cited in alphabetical order CH 2 CH 2 CHCH 2CHCH 2CH Br OH 6-bromo-4-ethyl-2-heptanol H 3C OH 2-ethyl-5-methylcyclohexanol HO 3,4-dimethylcyclopentanol CH 2CH 2CH 2NH 2 1-butanamine or butan-1-amine Nomenclature of Amines CH 2CHCHCH 2 NHCH 2 N-ethyl-3-hexamine or N-ethylhexan-3-amine CH 2CH 2NCH 2 N-ethyl-N-methyl-1-propanamine or N-ethyl-N-methylpropan-1-amine The substituents are listed in alphabetical order and a number or an N is assigned to each one 4 3 CHCH 2CH 2N Cl 2 3-chloro-N-methyl-1-butanamine 1 CH 2 NHCH 2CH CH 2CHCHCH NHCH 2 N-ethyl-5-methyl-3-hexanamine Br CHCHCH N H 3C 4-bromo-N,N-dimethyl-2-pentanamine 2-ethyl-N-propylcyclohexanamine

8 Naming Quaternary Ammonium Salts H 3C N + - HO tetramethylammonium hydroxide CH 2CH N Cl ethyldimethylpropylammonium chloride Structures of Alkyl Halides Structures of Alcohols and Ethers

9 Structures of Amines Physical properties are determined by attractive forces: van der Waals forces Dipole dipole interactions Hydrogen bonds The greater the attractive forces between molecules, the higher is the boiling point of the compound van der Waals Forces The boiling point of a compound increases with the increase in van der Waals force

10 Dipole Dipole Interaction Dipole dipole interactions are stronger than van der Waals force but weaker than ionic or covalent bonds A hydrogen bond is a special kind of dipole dipole interaction Across: similar MW, different functional group Down: Same functional group, increasing MW

11 Why do alkyl fluorides have lower boiling points than analogous alkyl iodides? Intermolecular forces also determine solubilities: like dissolves like Polar compound dissolves in polar solvent Nonpolar compound dissolves in nonpolar solvent Conformations of Alkanes: Rotation about Carbon Carbon Bonds

12 Different Conformations of Ethane A staggered conformer is more stable than an eclipsed conformer Torsional strain: repulsion between pairs of bonding electrons Conformations of n-butane Steric strain: repulsion between the electron clouds of atoms or groups Note: the lettering here is wrong! Conformation of Cycloalkanes: Ring Strain Angle strain results when bond angles deviate from the ideal bond angle

13 Angle strain 3 kinds of strain exist: Torsional strain Steric strain The chair conformation of cyclohexane is free of strain Ring Flipping in Cyclohexane

14 Drawing Cyclohexane The Conformations of Cyclohexane and Their Energies Conformations of Monosubstituted Cyclohexanes

15 Steric Strain of 1,3-Diaxial Interaction in Methylcyclohexane The larger the substituent on a cyclohexane ring, the more the equatorial substituted conformer will be favored K eq = [equatorial conformer]/[axial conformer] Conformations of Disubstituted Cyclohexanes The Chair Conformers of cis-1,4-dimethylcyclohexane H H H ring-flip H 3 C H cis-1,4-dimethylcyclohexane

16 The Chair Conformers of trans-1,4- Dimethylcyclohexane H H 3 C ring-flip H H H trans-1,4-dimethylcyclohexane 1-tert-Butyl-3-Methylcyclohexane

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