chapter2 - Organic Chemistry William H Brown Christopher S...

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2- 2-1 Organic Organic Chemistry Chemistry William H. Brown William H. Brown Christopher S. Foote Christopher S. Foote Brent L. Iverson Brent L. Iverson
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2- 2-2 Alkanes Alkanes and and Cycloalkanes Cycloalkanes Chapter 2 Chapter 2
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2- 2-3 Structure Structure Hydrocarbon: Hydrocarbon: a compound composed only of carbon and hydrogen Saturated hydrocarbon: Saturated hydrocarbon: a hydrocarbon containing only single bonds Alkane: Alkane: a saturated hydrocarbon whose carbons are arranged in an open chain Aliphatic hydrocarbon: Aliphatic hydrocarbon: another name for an alkane
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2- 2-4 Hydrocarbons Hydrocarbons H-C C-H H-C-C-H H H H H H C C H H H Hydrocarbons Alkanes (Chapter 2) Alkenes (Chapters 5-6) Alkynes (Chapter 7) Arenes (Chapter 21-22) Only carbon- carbon single  bonds One or more  carbon-carbon double bonds One or more carbon-carbon triple bonds One or more benzenelike rings Class Example Carbon- carbon bonding Name Ethane Ethene Acetylene Benzene Saturated Unsaturated
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2- 2-5 Structure Structure Shape tetrahedral about carbon all bond angles are approximately 109.5°
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2- 2-6 Drawing Alkanes Drawing Alkanes Line-angle formulas an abbreviated way to draw structural formulas each vertex and line ending represents a carbon CH 3 CH 2 CH 2 CH 3 CH 3 CH 2 CH 3 CH 3 CH 2 CH 2 CH 2 CH 3 Pentane Butane Propane Structural formula Line-angle  formula Ball-and- stick model
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2- 2-7 Constitutional Isomerism Constitutional Isomerism Constitutional isomers: Constitutional isomers: compounds with the same molecular formula but a different connectivity of their atoms example: C 4 H 10 CH 3 CH 2 CH 2 CH 3 Butane (bp -0.5 ° C) CH 3 CH 3 CHCH 3 2-Methylpropane (bp -11.6 ° C)
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2- 2-8 Constitutional Isomerism Constitutional Isomerism do these formulas represent constitutional isomers? find the longest carbon chain number each chain from the end nearest the first branch compare chain lengths as well the identity and location of branches CH 3 CHCH 2 CH CH 3 CH 3 CH 3 CH 3 CH 2 CHCHCH 3 CH 3 CH 3 and (each is C 7 H 16 ) CH 3 CH 2 CHCHCH 3 CH 3 CH 3 CH 3 CHCH 2 CH CH 3 CH 3 CH 3 4 4 5 4 3 1 and 5 1 1 2 2 3 3 5 2 5 4 3 2 1
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2- 2-9 Constitutional Isomerism Constitutional Isomerism World population World population is about is about 6,000,000,000 6,000,000,000 4,111,846,763 4,347 75 3 1 Constitutional  Isomers Molecular Formula CH 4 C 5 H 1 2 C 1 0 H 2 2 C 1 5 H 3 2 C 3 0 H 6 2 36,797,588 C 2 5 H 5 2
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2- 2- 10 10 Nomenclature - IUPAC Nomenclature - IUPAC Suffix - ane ane specifies an alk ane ane Prefix tells the number of carbon atoms undec- dodec- tetradec- pentadec- hexadec- heptadec- nonadec- eicos- tridec- 11 12 13 14 15 16 17 octadec- 18 19 20 Prefix meth- eth- prop- but- pent- hex- oct- non- dec- 1 2 3 4 5 6 7 hept- 8 9 10 Carbons Carbons Prefix
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2- 2- 11 11 Nomenclature - IUPAC Nomenclature - IUPAC Parent name: Parent name: the longest carbon chain Substituent: Substituent: a group bonded to the parent chain alkyl group alkyl group : a substituent derived by removal of a hydrogen from an alkane; given the symbol R- Alkane Alkyl group CH 4 Name Name Methane CH 3 - Methyl group CH 3 CH 3 Ethane CH 3 CH 2 - Ethyl group
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