1 Nomenclature SORAAI SAELIM SORAAI SAE-LIM
2 Nomenclature of Alkanes 1. Common name 2. IUPAC name (International Union of Pure and Applied Chemistry)
Shapes of Alkanes 3
Number of Carbon atoms Meth C=1 Eth C=2 Prop C=3 Buta C=4 Pent C=5 Hexa C=6 Hept C=7 Oct C=8 Non C=9 Dec C=10 4
5 C = 1 Meth C = 2 Eth C = 3 Prop C = 4 But C = 5 Penta C = 6 Hex C = 7 Hept C = 8 Oct C = 9 Non C = 10 Dec C = 11 Undec C = 12 Dodec C = 13 Tridec C = 14 Tetradec C = 15 Pentadec C = 16 Hexadec C = 17 Heptadec C = 18 Octadec C = 19 Nonadec C = 20 Icos C = 21 Henicos C = 22 Docos C = 23 Tricos C = 24 Tetracos C = 25 Pentacos C = 26 Hexacos C = 27 Heptacos C = 28 Octacos C = 29 Nonacos C = 30 Triacont C = 31 Hentriacont C = 32 Dotriacont C = 33 Tritriacont C = 40 Tetracont C = 50 Pentacont C = 60 Hexacont C = 70 Heptacont C = 80 Octacont C = 90 Nonacont C = 100 Hect C = 132 Dotriacontahect Number of Carbons
6 Rule of IUPAC name (International Union of Pure and Applied Chemistry) 1. The Main Chain Find the longest continuous chain of carbon atoms, and use the same of this chain as the base name of the compound. 2 H 3 C Substituent group 2-2 - 2-2 - main Chain
7 Substituent group alkyl groups. Structure - - 2 - - 2-2 - - 2-2 - 2 - - 2-2 - 2-2 - Name methyl ethyl propyl butyl pentyl
8 The Comparison name of alkyl groups and alkane. Structure of alkyl groups Name Structure of alkane Name - methyl -H methane - 2 - ethyl - 2 -H ethane - 2-2 - propyl - 2-2 -H propane - 2-2 - 2 - butyl - 2-2 - 2 -H butane - 2-2 - 2-2 - pentyl - 2-2 - 2-2 -H pentane These alkyl groups have names that end in yl.
9 Phalkyl. Substituent groups Structure Name Abbreviation - Methyl Me- - 2 - Ethyl Et- - 2-2 - Propyl Pr- Phenyl - 2-2 - 2 - Butyl Bu-
10 Ex. 1 Main Chain IUPAC Name octane H 3 C 2 C 2 2 2 2 Substituent group 4-ethyl- 2 4-methyl- 4- ethyl- 4-methyl octane
Case I IUPAC Name 11 2 2 WRONG Ex. 2 Case II Seven-carbon chain, but only three substituents 2 CORRECT 2 Seven-carbon chain, four substituents
Organizing Multiple Groups 12 When two or more of the same alkyl substituent are present, use the prefixes di- means 2 tri- means 3 tetra- means 4 penta- means 5 hexa- means 6 Methyl-substituent groups 2 4- substituent groups Prefix = tetra-
13 Ex. 3 IUPAC Name Numbering the Main Chain 2 2
14 incorrect IUPAC Name correct 4 3 1 2 5 6 2 2 4 5 2 7 2 6 3 2 7 1 3 5-ethyl- 3, 4, 6-tri-methyl- 2, 4, 5-tri-methyl- 3-ethyl-
15 Ex. 4 Numbering the Main Chain IUPAC Name 2 3 1 2 2 incorrect H 3 C C H 3 C 4 C 5 6 7
2 Br H 3 C 2-2 - 2-2 - Ex.5 Case I 16 H 3 C 2 Br 2-2 - 2-2 - IUPAC Name Case II H 3 C 2 Br 2-2 - 2-2 -
17 Halogen substituent groups Substituent groups Br Cl F I Name Bromo Chloro fluoro Iodo
18 Ex.6 IUPAC Name Ex.7 IUPAC Name 2 2 2 2 Br 2 2 Cl 2 2 Ph
19 Ex.8 Ex.9 Pr Br Br Br
20 Ex.10 Cyclo Ex.11
21 SORAAI SAELIM EX12: Draw the structure and give the molecular formula for each of the following compounds. 1. 3-ethyl octane 2. 2,3-di-methyl-4-propyl nonane
22 Ex.13 1 2 4-(1 -methyl ethyl)
23 - methyl group - 2 - ethyl group Some common alkyl groups - 2-2 - propyl group or n-propyl group - 2-2 - 2 - butyl group or n-butyl group H 3 C H 3 C 2 H 3 C isopropyl group H 3 C isobutyl group Characteristic of iso groups
24 H 3 C H 3 C The names of the secondary-butyl (sec-butyl) and tertiary-butyl (tert-butyl or t- butyl) groups are based on the degree of alkyl substitution of the carbon atom attached to the main chain. H R R R C R C R C H H R a primary carbon a secondary carbon a tertiary carbon
25 TEST_1 SORAAI SAELIM
26 Ex.14 SORAAI SAELIM Ex.15 Br Cl
27 SORAAI SAELIM Ex.16 Ex.17 OH F
28 Rule of IUPAC name (Cont.) SORAAI SAELIM 1.Select the longest chain containing the functional group 2.Change the suffix name of the corresponding parent alkane from -ane to. 2.1 Alcohol (R-OH) : cut -e and add ol 2.2 Aldehyde (R-O) : cut -e and add al 2.3 Ketone (R-CO-R) : cut -e and add one 2.4 Carboxylic acid (R-COOH) : cut -e and add oic acid 2.5 Amine (R-NH2) : cut -e and add amine 2.6 Amide (R-CO-NH2) : cut -e and add amide
29 Ex.18 Br O Ex.19 SORAAI SAELIM OH
30 Rule of IUPAC name (Cont.) 1 2 3
31 Ex.20 Ex.21 Ex.22
32 Rule of IUPAC name (Cont.) 1 2 3
33 Test_2 NH 2 O H
34 Isomers Same formula Different structure Different molecule with different properties must have a different name! Isomers are different compounds with the same molecular formula.
35 Isomers are different compounds with the same molecular formula. Constitutional isomers Constitutional isomers (Structural isomers) are isomers that differ in the order in which atoms are boned together. Structural isomers Positional Isomerism Skeletal Isomerism or Chain Isomerism Functional Isomerism
36 SORAAI SAELIM Isomers Constitutional isomers Stereo isomers Enantiomers Diastereomers
37 Skeletal Isomerism (Chain Isomerism) or Positional Isomerism Isomer of C 4 H 10
38 Isomer C5H12 C6H14
C7H16 39
40 Number of alkane isomers Molecular Formula Possible Number of constitutional Isomers Molecular Formula Possible Number of constitutional Isomers C 4 H 10 2 C 15 H 32 4,347 C 5 H 12 3 C 20 H 42 366,319 C 6 H 14 5 C 30 H 62 4,111,846,763 C 7 H 16 9 C 40 H 82 62,481,801,147,341 C 8 H 18 18 C 9 H 20 35 C 10 H 22 75
41 Cis trans Cis trans Cis : Having similar group on the same side of a double bond or a ring. trans : Having similar group on opposite side of a double bond or a ring. Z : Having the higher-priority groups on the same side of a double bond or a ring. E : Having the higher-priority groups on opposite side of a double bond or a ring.
42 Sigma Bonds and Bond Rotation The staggered conformation The eclipsed conformation
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46 SORAAI SAELIM Conformations of cyclohexane The chair conformation The boat conformation
47 SORAAI SAELIM Substituted Cyclohexanes: Axial and Equatorial Hydrogen Atoms
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49 SORAAI SAELIM Disubstitued Cycloalkanes Can exist as pairs of cis-trans stereoisomers Cis: groups on same side of ring Trans: groups on opposite side of ring
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51 SORAAI SAELIM Bicyclic and Polycyclic Alkanes
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