ORGANIC CHEMISTRY

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 Chapter 7: ALKYNES
An sp
hybridized
carbon

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 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

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for C=C
 PREPARATION OF ALKYNES
Sources of acetylene

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Alkynes by elimination reactions

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Alkynes could be obtained from alkenes after 2 steps

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REACTIONS OF ALKYNES
Additions of hydrogen halides (AE)

Markovnikov’s rule

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Additions of halogens (AE)

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 Additions of water – hydration reactions

Terminal alkynes are less reactive than internal alkynes,

need Hg2+ as a catalyst

Markovnikov’s rule

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Additions of boran – hydroboration & oxidation

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 Regioselectivity

Markovnikov’s rule

Anti-Markovnikov 13
 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determination, but has been superseded by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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Acidic hydrogen

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Only for primary alkyl halides

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Exercise Complete the following reactions:

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Exercise
Complete following reactions and
determine all stereoisomers of products:

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Exercise
Complete following reactions and
determine all stereoisomers of products:

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Exercise
From starting materials, prepare following compounds
(can use inorganic chemicals, peroxide,
bases, boron compound and solvents):

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