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
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Chapter 4: ALKANES

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NOMENCLATURE OF ALKANES

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ALKYL SUBSTITUENTS

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IUPAC NAMES OF BRANCHED
ALKANES

Determine the parent hydrocarbon – the

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longest continuous carbon chain
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• Substituents are listed
in alphabetical order
• Carbon chain is
numbered with the
lowest possible number
in the compound

Substituents are
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the same

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• Di, tri, tetra, n, sec, and tert are ignored in alphabetizing
substituents
• Iso, neo, and cyclo are not ignored

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NATURAL SOURCES OF ALKANES
C1-4

C5-11

Natural gas &

C9-16
petroleum
(fossil fuels) C15-25

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 PREPARATION OF ALKANES

Catalytic
hydrogenations
of alkenes /
alkynes

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Reduction reactions

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 Wurtz reactions symmetric alkane

Limitations:
+ 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
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halides are bulky at the halogen-attached carbon

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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

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the limitations of the Wurtz reaction
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 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

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HALOGENATION OF ALKANES

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 PRODUCT DISTRIBUTION

It must be easier to abstract a hydrogen atom from a

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secondary carbon than from a primary carbon

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Reactivity - relative rate at which a particular hydrogen is
abstracted in chlorination reactions:

At room
temperature

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Product distribution can be estimated:

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Br2 is less reactive towards alkane than Cl2, but Br2 is
more selective

Bromination at 125 oC

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 Too violent

Too slow

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 STEREOCHEMISTRY OF RADICAL
SUBSTITUTION REACTIONS

Have no
asymetric
carbon

Racemic
mixture
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Already have
1 asymetric
carbon

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COMBUSTION OF ALKANES

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