Organic Chemistry, 5th ed. Marc Loudon. Chapter 2 Alkanes. Eric J. Kantorows ki California Polytechnic State University San Luis Obispo, CA

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1 Organic Chemistry, 5th ed. Marc Loudon Chapter 2 Alkanes Eric J. Kantorows ki California Polytechnic State University San Luis Obispo, CA

2 Chapter 2 Overview 2.1 Hydrocarbons 2.2 Unbranched Alkanes 2.3 Conformations of Alkanes 2.4 Constitutional Isomers and Nomenclature 2.5 Cycloalkanes and Skeletal Structures 2.6 Physical Properties of Alkanes 2.7 Combustion 2.8 Occurrence and Use of Alkanes 2.9 Functional Groups, Compound Classes, and the R Notation 2

3 Hydrocarbons Compounds that contain only carbon and hydrogen Two classes: Aliphatic and aromatic 2.1 Hydrocarbons 3

4 Unbranched Alkanes Referred to as normal or n-alkanes Possess a linear carbon chain Lewis structure: Condensed formulas: 2.2 Unbranched Alkanes 4

5 Nomenclature of n-alkanes 2.2 Unbranched Alkanes 5

6 Conformational Isomers Rotation about a single bond leads to a series of conformers A Newman projection is a visual tool to inspect conformers as viewed down a bond 2.3 Conformations of Alkanes 6

7 Newman Projections 2.3 Conformations of Alkanes 7

8 Staggered and Eclipsed Conformers Two energetic extremes are found for ethane Other dihedral angles are possible 2.3 Conformations of Alkanes 8

9 Energy vs Dihedral Angle 2.3 Conformations of Alkanes 9

10 Butane 2.3 Conformations of Alkanes 10

11 Conformations of Butane Additional conformers are possible for butane 2.3 Conformations of Alkanes 11

12 Energy vs Dihedral Angle 2.3 Conformations of Alkanes 12

13 Space-Filling Models of Butane Conformers van der Waals repulsion creates a torsional strain encouraging rotation towards a more stable conformer The most stable conformer dominates 2.3 Conformations of Alkanes 13

14 Conformational Analysis Staggered conformers are preferred van der Waals repulsion influences conformer populations Rotation about single bonds is rapid except at very low temperatures 2.3 Conformations of Alkanes 14

15 Isomers Different compounds with the same molecular formula Isomers that differ in atom connectivity are constitutional isomers or structural isomers 2.4 Constitutional Isomers and Nomenclature 15

16 Organic Nomenclature Standardized by International Union of Pure and Applied Chemistry (IUPAC) The current system is called substitutive nomenclature Rules for alkane nomenclature extend to most other compound classes Apply the following 10 rules in order 2.4 Constitutional Isomers and Nomenclature 16

17 Substitutive Nomenclature of Alkanes 1. Unbranched alkanes are named according to number of carbons 2. If branched, determine the principle chain 2.4 Constitutional Isomers and Nomenclature 17

18 Substitutive Nomenclature of Alkanes 3. If two chains are equal in length, select the one with the most substituents 4. Number the principle chain, giving the lower number to the first branching point 2.4 Constitutional Isomers and Nomenclature 18

19 Substitutive Nomenclature of Alkanes 5. Name each branch and identify its location on the principle chain Branching groups are called substituents Those derived from alkanes are alkyl groups 2.4 Constitutional Isomers and Nomenclature 19

20 Substitutive Nomenclature of Alkanes Some short branched-chain alkyl groups: 2.4 Constitutional Isomers and Nomenclature 20

21 Substitutive Nomenclature of Alkanes 6. Construct the name with number, substituent, and principle chain (note the hyphen) This is a constitutional isomer of heptane It has 7 carbons, but is named as a derivative of hexane 2.4 Constitutional Isomers and Nomenclature 21

22 Substitutive Nomenclature of Alkanes 7. For multiple groups, each gets its own number Include prefixes di-, tri-, tetra- 2.4 Constitutional Isomers and Nomenclature 22

23 Substitutive Nomenclature of Alkanes 8. For multiple substituents, select the numbering scheme that gives the smaller number at first point of difference 2.4 Constitutional Isomers and Nomenclature 23

24 Substitutive Nomenclature of Alkanes 9. Cite substituents in alphabetical order regardless of location Di-, tri-, tetra-, and hyphenated prefixes tertand sec- are ignored Iso-, neo-, cyclo- are not ignored 2.4 Constitutional Isomers and Nomenclature 24

25 Substitutive Nomenclature of Alkanes 10. If the numbering of different groups is not resolved, the first-cited group gets the lowest number 2.4 Constitutional Isomers and Nomenclature 25

26 Highly Condensed Structures Highly condensed structures are commonly used 2.4 Constitutional Isomers and Nomenclature 26

27 Classification of Carbon Substitution Primary carbon: Bonded to 1 other carbon Secondary carbon: Bonded to 2 other carbons Tertiary carbon: Bonded to 3 other carbons Quaternary carbon: Bonded to 4 other carbons 2.4 Constitutional Isomers and Nomenclature 27

28 Classification of Carbon Substitution Similarly, hydrogens may also be classified as primary, secondary, tertiary, or quaternary 2.4 Constitutional Isomers and Nomenclature 28

29 Cycloalkanes Alkanes with closed loops or rings Add the prefix cyclo Note that cyclohexane has 2 less hydrogens than hexane 2.5 Cycloalkanes and Skeletal Structures 29

30 Skeletal Structures An important (and time-saving!) structuredrawing convention Each vertex represents a carbon Enough hydrogens are understood to be present to complete carbon s tetravalency 2.5 Cycloalkanes and Skeletal Structures 30

31 Skeletal Structures Also useful for open-chain alkanes The terminus of a line is a CH Cycloalkanes and Skeletal Structures 31

32 Nomenclature of Cyloalkanes The same nomenclature rules are followed Do not forget the cyclo part of the name 2.5 Cycloalkanes and Skeletal Structures 32

33 Cycloalkanes as a Substituent If the noncyclic carbon chain contains more carbons than the ring 2.5 Cycloalkanes and Skeletal Structures 33

34 Boiling Points Boiling point: Temperature at which vapor pressure of substance = atmospheric pressure B.p. of unbranched alkanes increases by C per carbon Homologous series: differs by CH 2 groups 2.6 Physical Properties of Alkanes 34

35 Intermolecular Interactions for Alkanes Electron clouds can be temporarily distorted 2.6 Physical Properties of Alkanes 35

36 Intermolecular Interactions for Alkanes Induced dipole van der Waals attraction (or a dispersion interaction) Greater intermolecular forces = higher b.p. 2.6 Physical Properties of Alkanes 36

37 Molecular Shape and Boiling Point Greater branching = lower b.p. Molecules that are spherical have less surface area 2.6 Physical Properties of Alkanes 37

38 Melting Points Melting point: Temperature at which a substance transforms from solid to liquid A narrow m.p. is an indicator of purity Branching interferes with crystal packing leading to lower m.p. values Symmetric molecules tend to have unusually high m.p.s 2.6 Physical Properties of Alkanes 38

39 Melting Points M.p. increases with number of carbons 2.6 Physical Properties of Alkanes 39

40 Other Physical Properties Dipole moment: A measure of polarity Solubility: Important for determining which solvents can be used (e.g., for reactions) Density: Determines whether a compound will be the upper of lower layer if mixed with an immiscible liquid (e.g., alkane + water) 2.6 Physical Properties of Alkanes 40

41 Combustion Alkanes are the least reactive organic compounds Alkanes react rapidly with O 2 in combustion A commercially important reaction with increasingly significant global impact Analytically useful for determining molecular formula 2.7 Combustion 41

42 The Petroleum Feedstock Most alkanes come from petroleum Composed mostly of alkanes and aromatic hydrocarbons Purified via fractional distillation 2.8 Occurrence and Use of Alkanes 42

43 Industrial Fractionation of Petroleum 2.8 Occurrence and Use of Alkanes 43

44 Functional Groups A functional group is a characteristically bonded group of atoms Each functional group exhibits its own particular chemical reactivity Alkanes may be viewed as the blank template upon which functional groups are placed 2.9 Functional Groups, Compound Classes, and the R Notation 44

45 Compound Classes Compounds with the same functional group comprise a compound class Some compounds may contain more than one functional group 2.9 Functional Groups, Compound Classes, and the R Notation 45

46 The R and Ph Notation A convenient way to represent a generic structure or portion of a molecule R Notation: R represents all alkyl groups The phenyl group may be represented by Ph- 2.9 Functional Groups, Compound Classes, and the R Notation 46

47 The Ar Notation Use Ar- for more highly substituted rings 2.9 Functional Groups, Compound Classes, and the R Notation 47

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