Chapter 1: ISOMERISM

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Isomers: Compounds with the same molecular formula but different structural formulas. Different compounds that have the same molecular formula – but differ in their connectivity. Isomers that differ in the way their atoms are arranged in space

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Nội dung Text: Chapter 1: ISOMERISM

ORGANIC CHEMISTRY Dr Nam T. S. Phan Faculty of Chemical Engineering HCMC University of Technology Office: room 211, B2 Building Phone: 8647256 ext. 5681 Email: ptsnam@hcmut.edu.vn 1
REFERENCES [1] Nam T. S. Phan, Hoa T. V. Tran ‘Organic chemistry’, VNU-HCMC Publisher, 2010 [2] Nam T. S. Phan, ‘Study guide to organic chemistry’, VNU-HCMC Publisher, 2009 [3] Paula Y. Bruice, ‘Organic chemistry’, fifth edition, Pearson Prentice Hall, 2007 [4] Francis A. Carey, ‘Organic chemistry’, fifth edition, McGraw-Hill, 2003 [5] Paula Y. Bruice, ‘Study guide and solutions manual - Organic chemistry’, fifth edition, Pearson Prentice Hall, 2007 [6] Graham T.W. Solomons, Craig B. Fryhle, ‘Organic chemistry’, eighth edition, John Wiley & Sons, 2004 2
COURSE OUTLINE • Isomerism • Electronic & steric effects • Common reaction mechanisms • Alkanes • Alkenes • Alkadienes • Alkynes • Aromatic hydrocarbons • Alkyl halides • Alcohols & phenols • Aldehydes & ketones • Carboxylic acids • Amines & diazoniums 3
Chapter 1: ISOMERISM Isomers: Compounds with the same molecular formula but different structural formulas Isomers Constitutional isomers Stereoisomers Conformational isomers Configurational isomers Optical isomers /Enantiomers & Geometric isomers Diastereoisomers 4
CONSTITUTIONAL ISOMERS Different compounds that have the same molecular formula – but differ in their connectivity 5
STEREOISOMERS Isomers that differ in the way their atoms are arranged in space Conformational isomers Configurational isomers 6
CONFORMATIONAL ISOMERS • Different shapes of the same molecule resulting from rotation around a single C-C bond • Conformational isomers are not different compounds 7
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Conformations of butane 10
Conformations of cyclohexane 11
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GEOMETRIC ISOMERS There is no rotation around the C=C bond 15
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The E,Z system of nomenclature 17
Cahn-Ingold-Prelog priority rules Rule 1 Rule 2 18
Rule 3 Rule 4 19
OPTICAL ISOMERS A chiral opbject Nonsuperimposable mirror image An achiral opbject 20