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Alkynes - Organic Chemistry

Alkynes - Organic Chemistry

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Published by Mark
A study guide about alkynes for organic chemistry.
A study guide about alkynes for organic chemistry.

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Published by: Mark on Feb 18, 2009
Copyright:Attribution Non-commercial

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05/04/2014

 
C40mmp handout 1
ALKYNES
Alkynes (C
n
H
2n-2
) are hydrocarbons that contain a carbon-carbontriple bond.STRUCTURE AND NOMENCLATUREIn the IUPAC system of nomenclature, the rules for alkynes aresimilar to those for alkenes, except that the ending –yne replaces –ene.Ethyne or acetylene (its common name) is the simplest member ofthe alkyne family. Propyne is the second.Alkynes of four or more carbons can have different positions for thecarbon-carbon triple bond and can be classified as either internal orterminal depending on the location of the triple bond. Note that terminalalkynes have a hydrogen directly attached to the sp-hybridized carbon.
HCCHCH
3
CCHethyne(acetylene)propyne
InternalTerminalCH
3
CCCH
3
CH
3
CH
2
CCHCH
3
CH
2
CCCH
2
CH
3
CH
3
CH
2
CH
2
CH
2
CCHCH
3
CCCHCHCH
2
CCHCH
3
CH
3
H
3
CCH
3
2-butyne1-butyne3-hexyne1-hexyne4-methyl-2-pentyne4-methyl-1-pentyne
 
C40mmp handout 2
Cycloalkynes are the cyclic analogs of alkynes. The eight-membered ring is the smallest ring that can form a stable cycloalkyne.PREPARATION:In general, alkynes may be prepared from thedehydrohalogenation of vicinal or 1,2 – dihalides with strong base, e.g.conc. KOH or NaNH
2
.PHYSICAL PROPERTIESAlkynes are very weakly polar and have essentially the samephysical properties as alkanes and alkenes. The examples belowillustrate the effect of molecular size and chain-branching on boiling point.
cyclooctyne
HCCCH
2
CH
2
CH
3
BP 40 °CHCCCH
2
CH
2
CH
2
CH
3
BP 72 °CHCCCHCH
3
CH
3
HCCCCH
3
CH
3
CH
3
BP 29 °CBP 38 °C
 
BrBrHH2 NaNH
2
CCex.CBrCBrHH2 NaNH
2
CCor conc KOHor conc KOH
 
 
C40mmp handout 3
REACTIONSThe
π
electrons in alkynes are held loosely as in the alkenes. Thus,alkynes also undergo addition reactions, many of which are electrophilicaddition reactions. As a general rule, reagents add to alkynes in the sameway that they add to alkenes. However, for alkynes to be transformed to asaturated product, two molar equivalents of the adding reagent arenecessary.I. Hydrogenation
CCXYCCYXXYCCYXXY
CC2H
2
Ni, Pt or PdNa or Liliq NH
3
H
2
Lindlar's catalystCCHHHHCCHHCCHHalkane
trans 
-alkene
cis 
-alkene

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