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BÀI GIẢNG ORGANIC CHEMISTRY chapter7

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


Chapter 7:

ALKYNES

An sp
hybridized
carbon

2



NOMENCLATURE OF ALKYNES
The IUPAC name of an alkyne is obtained by replacing
the “ane” ending of the corresponding alkane with “yne”

In common nomenclature, alkynes are named as
‘substituted acetylenes’
Both ethyne & acetylene are acceptable names for C2H2
3


Lowest possible number, regardless of which
functional group gets the lower number

The same low number for both directions, lower number
4
for C=C


PREPARATION OF ALKYNES
Sources of acetylene

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Alkynes by elimination reactions

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REACTIONS OF ALKYNES
Acidic hydrogen

7


Only for primary alkyl halides

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Additions of hydrogen halides (AE)

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Additions of halogens (AE)

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Additions of water – hydration reactions

Markovnikov’s rule

Terminal alkynes are less reactive than internal alkynes,
need Hg2+ as a catalyst

11


Additions of boran – hydroboration & oxidation

12


Regioselectivity
Markovnikov’s rule

Anti-Markovnikov

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Additions of hydrogen – hydrogenation
Product is
alkane

Product is
alkene

14


Ozonolysis of alkynes

Ozonolysis used to be employed in structure
determination, but has been superseded by
spectroscopic methods
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Polymerizations

16



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