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Bài giảng Organic chemistry - Chapter 4: Alkanes - 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 4: ALKANES  
2
NOMENCLATURE OF ALKANES  
ALKYL SUBSTITUENTS  
IUPAC NAMES OF BRANCHED  
ALKANES  
Determine the parent hydrocarbon – the  
longest continuous carbon chain  
5
• Substituents are listed  
in alphabetical order  
• Carbon chain is  
numbered with the  
lowest possible number  
in the compound  
Substituents are  
the same  
6
• Di, tri, tetra, n, sec, and tert are ignored in alphabetizing  
substituents  
• Iso, neo, and cyclo are not ignored  
8
NATURAL SOURCES OF ALKANES  
C1-4  
C5-11  
Natural gas &  
C9-16  
petroleum  
(fossil fuels)  
C15-25  
9
PREPARATION OF ALKANES  
Catalytic  
hydrogenations  
of alkenes /  
alkynes  
10  
Reduction reactions  
11  
Wurtz reactions  
Limitations:  
symmetric alkane  
+ The Wurtz reaction is limited to the synthesis of symmetric  
alkanes from alkyl iodides & bromides  
+ If two dissimilar alkyl halides are taken as reactants, then  
the product is a mixture of alkanes that is, often, difficult to  
separate  
+ A side reaction also occurs to produce an alkene  
+ The side reaction becomes more significant when the alkyl  
12  
halides are bulky at the halogen-attached carbon  
Corey-House synthesis – the reaction of a lithium dialkyl  
cuprate with an alkyl halide to form a new alkane  
Corey-House synthesis overcomes some of  
the limitations of the Wurtz reaction  
13  
REACTIVITY OF ALKANES  
• Alkanes have only strong σ bonds  
• Electronegativity of C & H are approximately  
the same  
• None of the atoms in alkanes have any  
significant charge  
• Neither nucleophiles nor electrophiles are  
attracted  
Alkanes are very unreactive  
14  
HALOGENATION OF ALKANES  
PRODUCT DISTRIBUTION  
It must be easier to abstract a hydrogen atom from a  
secondary carbon than from a primary carbon  
18  
Reactivity - relative rate at which a particular hydrogen is  
abstracted in chlorination reactions:  
At room  
temperature  
19  
Product distribution can be estimated:  
20  
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