Bài giảng Organic chemistry - Chapter 7: Alkynes - Phan Nam
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 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
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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
Only for primary alkyl halides
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
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Additions of boran – hydroboration & oxidation
2
Regioselectivity
Markovnikov’s rule
Anti-Markovnikov
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Additions of hydrogen – hydrogenation
Product is
alkane
Product is
alkene
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Ozonolysis of alkynes
Ozonolysis used to be employed in structure
determination, but has been superseded by
spectroscopic methods
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Polymerizations
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