Tài liệu Hóa hữu cơ organic chemistry dr nam t s phan

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: [email protected] http://hhud.tvu.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 http://hhud.tvu.edu.vn 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 http://hhud.tvu.edu.vn 3 Chapter 1: ISOMERISM Isomers: Compounds with the same molecular formula but different structural formulas Isomers Stereoisomers Constitutional isomers Conformational isomers Geometric isomers Configurational isomers Optical isomers /Enantiomers & Diastereoisomers http://hhud.tvu.edu.vn 4 CONSTITUTIONAL ISOMERS Different compounds that have the same molecular formula – but differ in their connectivity http://hhud.tvu.edu.vn 5 STEREOISOMERS Isomers that differ in the way their atoms are arranged in space Conformational isomers Configurational isomers http://hhud.tvu.edu.vn 6 CONFORMATIONAL ISOMERS • Different shapes of the same molecule resulting from rotation around a single C-C bond • Conformational isomers are not different compounds http://hhud.tvu.edu.vn 7 http://hhud.tvu.edu.vn 8 http://hhud.tvu.edu.vn 9 Conformations of butane http://hhud.tvu.edu.vn 10 Conformations of cyclohexane http://hhud.tvu.edu.vn 11 http://hhud.tvu.edu.vn 12 http://hhud.tvu.edu.vn 13 http://hhud.tvu.edu.vn 14 GEOMETRIC ISOMERS There is no rotation around the C=C bond http://hhud.tvu.edu.vn 15 http://hhud.tvu.edu.vn 16 The E,Z system of nomenclature http://hhud.tvu.edu.vn 17 Cahn-Ingold-Prelog priority rules Rule 1 Rule 2 http://hhud.tvu.edu.vn 18 Rule 3 Rule 4 http://hhud.tvu.edu.vn 19 OPTICAL ISOMERS A chiral opbject Nonsuperimposable mirror image An achiral opbject http://hhud.tvu.edu.vn 20