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Bài giảng Organic chemistry - Chapter 1: Isomeri - Phan Nam

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ORGANIC CHEMISTRY  
Dr Nam T. S. Phan  
Faculty of Chemical Engineering  
HCMC University of Technology  
Office: room 211, B2 Building  
Phone: 38647256 ext. 5681  
Email: ptsnam@hcmut.edu.vn  
1
REFERENCES  
[1] Nam T. S. Phan, Hoa T. V. Tran ‘Organic chemistry’,  
VNU-HCMC Publisher, 2011  
[2] Nam T. S. Phan, ‘Study guide to organic chemistry’,  
VNU-HCMC Publisher, 2011  
[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  
• Introduction to 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  
Stereoisomers  
Constitutional isomers  
Configurational isomers  
Conformational 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  
CONFORMATIONAL ISOMERS  
• Different shapes of the same molecule resulting  
from rotation around a single C-C bond  
• Conformational isomers are not different  
compounds  
7
8
Conformations of butane  
Conformations of cyclohexane  
11  
13  
14  
GEOMETRIC ISOMERS  
There is no rotation around the C=C bond  
15  
The E,Z system of nomenclature  
17  
Cahn-Ingold-Prelog priority rules  
Rule 1  
Rule 2  
Rule 3  
Rule 4  
OPTICAL ISOMERS  
A chiral opbject  
Nonsuperimposable  
mirror image  
An achiral object  
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