Chapter 7: ALKYNES

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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 C H

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Nội dung Text: Chapter 7: ALKYNES

ORGANIC CHEMISTRY Dr Nam T. S. Phan Faculty of Chemical Engineering HCMC University of Technology Office: room 211, B2 Building Phone: 8647256 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 C H 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 5
Alkynes by elimination reactions 6
REACTIONS OF ALKYNES Acidic hydrogen 7
Only for primary alkyl halides 8
E Additions of hydrogen halides (A ) 9
E Additions of halogens (A ) 10
Additions of water – hydration reactions Markovnikov’s rule Terminal alkynes are less reactive than internal alkynes, 2+ need Hg as a catalyst 11
Additions of boran – hydroboration & oxidation 12
Regioselectivity Markovnikov’s rule Anti-Markovnikov 13
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Ozonolysis of alkynes Ozonolysis used to be employed in structure determination, but has been superseded by spectroscopic methods 15
Polymerizations 16