Chapter 4 Alkanes and Cycloalkanes.! Structure, Nomenclature and Conformations
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1 hapter 4 Alkanes and ycloalkanes Structure, Nomenclature and onformations
2 arbon Bonding
3 Structural Representation of Simple Alkanes Name Kekule structure ondensed structure Model methane ethane propane butane Simple alkanes have the general formula n2n+2.
4 ydrocarbons The Simplest lass of Organic ompounds. ydrocarbons are further subclassified SATURATED UNSATURATED ALIPATI AROMATI
5 Nomenclature
6 Formulas and Properties of Normal Alkanes n Molecular ondensed Name Melting Boiling Formula Structural Formula point ( point ( 1 4 methane ethane propane butane pentane hexane heptane octane nonane decane
7 1º, 2º, 3º, and 4º arbons A carbon atom is classified as primary (1º), secondary (2º), tertiary (3º), or quaternary (4º) depending upon whether or not it is directly bonded to a total of one, two, three, or four other carbon atoms, respectively. 1 º 2 º 3 º 4 º
8 1º, 2º, 3º, and 4º arbons - Examples Indicate the number of primary, secondary, tertiary, and quaternary carbons in the following molecules: 1º: 5 2º: 2 3º: 1 4º: 1 1º: 2 2º: 2 3º: 2 4º: 0
9 ydrocarbon Nomenclature Why is the IUPA system Necessary? onsider the following carbon hydrides Each formula represents a unique compound. When structural formulas are considered, however, 37 has only 1 isomer. 410 has 2 isomers. 512 has 3 isomers. 614 has 5 isomers has 75 isomers has 4 x 10 9 isomers.
10 ydrocarbon Nomenclature Basis of the IUPA System of naming-the Root Name 1. The root name of a compound is derived from the longest continuous chain of carbon atoms or the longest continuous chain of carbon atoms containing a given special structural feature. a. ommon stems are used to indicate the length of carbon chains. meth-, eth-, pro-, but-, pent-, hex-, hept-, oct-, non-, dec- b. ommon suffixes indicate the class of compounds. Alkane Alkene Alkyne
11 ydrocarbon Nomenclature 2. If the carbon chain contains unsaturation (double or triple bonds), the carbon chain is numbered so as to give double or triple bond(s) the lowest number(s) Butene 2-Butene Butene 1-Butene
12 ydrocarbon Nomenclature Substituents may be attached to a carbon chain 1. Substituents which are not pieces of alkanes: F- Fluoro- -NO2 Nitro l- hloro- -N2 Amino Br- Bromo- -O ydroxy I- Iodo-
13 ydrocarbon Nomenclature 2. Substituents which are pieces of alkanes - Alkyl groups Names are derived from the parent alkanes. Parent alkane Methane When attached to another chain Parent hain Methyl- BASE NAME Parent hain Ethane Ethyl- BASE NAME
14 ydrocarbon Nomenclature 2. Substituents which are pieces of alkanes - Alkyl groups Parent alkane When attached to another chain Propane Parent hain Propyl- BASE NAME Also called a methyl ethyl group Parent hain Isopropyl- BASE NAME
15 ydrocarbon Nomenclature -Alkyl Groups Parent hain butyl- BASE NAME Parent hain s-butyl- BASE NAME butane Also called a 1-methyl propyl group
16 ydrocarbon Nomenclature -Alkyl Groups 2-methylpropane ( isobutane ) Parent hain Parent hain isobutyl- BASE NAME Also called a 2-methyl propyl group t-butyl- BASE NAME Also called a dimethyl ethyl group
17 ydrocarbon Nomenclature -Alkyl Groups Name Formula Line structure methyl- ethyl- ( propyl- 37- isopropyln-butyl- s-butyl- isobutyl- t-butyl- ( (
18 ydrocarbon Nomenclature -Final Step Position of Attachment ( Locant ) of Substituents is Indicated 1. For carbon chains with double or triple bonds (alkenes and alkynes), the numbering system for the base carbon chain has already been established and does not change. 2. For saturated carbon chains (alkanes) the numbering system for the base carbon chain is determined by the positions of the substituents. Substituent names (in alphabetical order) and numbers are added (prefixed) to the base name of the compound.
19 ydrocarbon Nomenclature Putting it Together for a Simple Alkane Position of alkyl groups Family 4-isopropyl-3-methyl heptane Base name Alkyl groups Longest chain
20 ydrocarbon Nomenclature A more complicated example l l 2 l l l 2 l l 3 l 2 2 l 1,3,5-trichloro-5-isobutyl-3,9-dimethyl decane 1,3,5-trichloro-3,9-dimethyl-5-(2-methylpropyl) decane
21 Name the following compound isopropylpentane 3-ethyl-2-methylpentane
22 ydrocarbon Nomenclature -Other arbon Groups Main chain Main chain Main chain Main chain Main chain cyclopropyl - cyclobutyl - cyclopentyl - cyclohexyl - phenyl -
23 ydrocarbon Nomenclature -yclic Alkanes 1. Structures are usually abbreviated 2. Planar representations do not represent 3-D shape.
24 ydrocarbon Nomenclature -yclic Alkanes 3. yclic structures are numbered and named to give the lowest numbers to substituents ,2-dimethylcyclopentane ,2,4-trimethylcyclohexane
25 Nomenclature of Bicyclic ompounds bicyclo [4.4.0] decane bicyclo [3.3.2] decane bicyclo [6.2.0] decane spiro [4,5] decane
26 cubane basketane housane churchane
27 Question: Are pentane and cyclopentane isomers???
28 Isomerism Two ompounds Are the connectivities of the atoms the same? Yes Are the compounds superimposable? Yes Are the chemical formulas the same? Yes No No No The compounds are not isomers. The compounds are constitutional isomers. The compounds are stereoisomers. The compounds are identical. Are the compounds mirror images? Yes No The compounds are enantiomers. The compounds are diastereomers.
29 Isomerism What is the relationship between these two molecules? 2,3-dimethylpentane 2,3-dimethylhexane
30 Isomerism What is the relationship between these two molecules? and 2,4-dimethylpentane 2,2-dimethylpentane
31 Isomerism What is the relationship between these two molecules? 2,3-dimethylpentane 2,3-dimethylpentane
32 ombustion of ydrocarbons
33 ombustion of ydrocarbons + O2 O O2 O2 + 2 O O2 2 O2 + 2 O O2 3 O O O2 4 O O O2 8 O O
34 ombustion of ydrocarbons n2n+2 + (n-alkane) (3n+1) 2 O2 no2 + (n+1) 2O + Δcomb (kj/mol) n Δ Δ
35 ombustion of ydrocarbons least stable O 2 8 O O º = kj/mol O 2 8 O O º = kj/mol most stable O 2 8 O O º = kj/mol 818
36 Sources of ydrocarbons
37 Boiling Points for Straight-hain Alkanes
38 Physical Properties of Alkanes The Basis for Fractional Distillation ot crude oil is fed in at t h e f o o t o f t h e fractionating column and mixed with steam. Various constituents, or fractions, of the crude oil separate at various points of the column.
39 Physical Properties of Alkanes The Basis for Fractional Distillation # s
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