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Bài giảng Organic chemistry - Chapter 5: Alkenes - 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: [email protected].vn  
1
Chapter 5: ALKENES  
An sp2  
hybridized  
carbon  
2
NOMENCLATURE OF ALKENES  
The IUPAC name of an alkene is obtained by replacing  
the “ane” ending of the corresponding alkane with “ene”  
• Ethylene is an acceptable synonym for ethene in the IUPAC  
system  
• Propylene, isobutylene and other common names ending in  
“ylene” are NOT acceptable IUPAC names  
3
Determine the parent  
hydrocarbon – the  
longest continuous  
carbon chain containing  
the C=C  
Note: Alkenes can have geometric isomers  
5
PREPARATION OF ALKENES  
Dehydrations of alcohols  
Acid  
isomerization  
6
isomerization  
7
Eliminations of alkyl halides  
Base  
8
Alkyne hydrogenations  
Pd/CaCO3 + Pb(OAc)2 / quinoline  
9
REACTIONS OF ALKENES  
Additions of hydrogen halides (AE)  
More stable  
10  
Markovnikov’s rule  
Carbocation rearrangement  
More stable  
11  
12  
More stable  
Stereochemistry  
13  
Racemic mixture  
Already has 1 asymmetric carbon  
14  
2 asymmetric carbons are created  
15  
Additions of hydrogen bromide (AR)  
Electrophilic addition (AE)  
Radical addition (AR) – only for HBr  
16  
Reaction  
mechanism:  
Additions of halogens  
18  
Major  
addition  
product –  
NOT a  
dihalide  
19  
Stereochemistry  
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