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{{chembox |
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{{chembox |
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| verifiedrevid = 403365671 |
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| Reference=<ref> at ]</ref><ref></ref> |
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| verifiedrevid = 401998552 |
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| Name = 2-Butyne |
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| Reference=<ref> at ]</ref><ref></ref> |
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| ImageFile1 = <chem>H3C-C#C-CH3</chem> |
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| Name = Dimethylacetylene |
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| ImageSize1 = 180px |
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| ImageFile1 = dimethylacetylene.png |
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| ImageName1 = Structural formula |
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| ImageSize1 = 180px |
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| ImageFile2 = 2-butyne-3D-balls-B.png |
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| ImageName1 = Structural formula |
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| ImageSize2 = 150px |
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| ImageFile2 = 2-butyne-3D-balls-B.png |
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| ImageName2 = Ball-and-stick model |
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| ImageSize2 = 150px |
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| PIN = But-2-yne <!-- Nomenclature of Organic Chemistry – IUPAC Recommendations and Preferred Names 2013 (Blue Book) --> |
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| ImageName2 = Ball-and-stick model |
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| OtherNames = Dimethylacetylene<br />Crotonylene |
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| IUPACName = But-2-yne |
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|Section1={{Chembox Identifiers |
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| OtherNames = Dimethylacetylene<br />Crotonylene |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| Section1 = {{Chembox Identifiers |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| ChemSpiderID = 9990 |
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| ChemSpiderID = 9990 |
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| PubChem = 10419 |
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| PubChem = 10419 |
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| CASNo_Ref = {{cascite|correct|CAS}} |
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| CASNo_Ref = {{cascite|correct|CAS}} |
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| CASNo = 503-17-3 |
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| CASNo = 503-17-3 |
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| UNII_Ref = {{fdacite|correct|FDA}} |
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| SMILES = C(#CC)C |
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| UNII = LKE6D3018E |
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| SMILES = C(#CC)C |
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| Section2 = {{Chembox Properties |
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|Section2={{Chembox Properties |
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| Formula = C<sub>4</sub>H<sub>6</sub> |
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| Formula = C<sub>4</sub>H<sub>6</sub> |
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| MolarMass = 54.0904 g/mol |
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| MolarMass = 54.0904 g/mol |
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| Density = 0.691 g/mL |
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| Density = 0.691 g/mL |
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| MeltingPtC = -32 |
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| MeltingPtC = -32 |
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| BoilingPtC = 27 |
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| BoilingPtC = 27 |
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'''Dimethylacetylene''' ('''crotonylene''' or '''2-butyne''') is an ] with ] ]]<sub>3</sub>]≡]]]<sub>3</sub>. Produced artificially, it is a colorless, volatile, pungent liquid at ]. |
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'''2-Butyne''' ('''dimethylacetylene''', '''crotonylene''' or '''but-2-yne''') is an ] with ] CH<sub>3</sub>C≡CCH<sub>3</sub>. Produced artificially, it is a colorless, volatile, pungent liquid at ]. |
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2-Butyne is of interest to physical chemists because of its very low ] and the problem of determining that barrier using high-resolution infrared spectroscopy. Analysis of its spectrum<ref>{{cite journal | last = di Lauro | first = C.|display-authors=etal| year = 1997 | title =The rotation-torsion structure in the ν11/ν15 (Gs) methyl rocking fundamental band in dimethylacetylene |
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| journal = J. Mol. Spectrosc.| volume = 184 | issue = 1 |
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| pages = 177–185 | doi =10.1006/jmsp.1997.7321}}</ref> |
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leads to a determination that the torsional barrier is only 6 cm<sup>−1</sup> (1.2{{e|-22}} J or 72 J mol<sup>−1</sup>). However, it has not been determined whether the equilibrium structure is eclipsed (D<sub>3h</sub>) or staggered (D<sub>3d</sub>). Symmetry analysis using the Molecular Symmetry Group<ref name=Longuet-Higgins1963>{{cite journal | last1 = Longuet-Higgins | first1 = H.C. | year = 1963 | title = The symmetry groups of non-rigid molecules | journal = Molecular Physics | volume = 6 | issue = 5| pages = 445–460 | doi = 10.1080/00268976300100501 | bibcode = 1963MolPh...6..445L | doi-access = free }}</ref><ref>{{cite journal | author1=P. R. Bunker | year=1964 |
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| title=The Rotation-Torsion Wavefunctions of Molecules that have two Identical Rotors |
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| journal=Mol. Phys. | volume=8 | page=81 | doi = 10.1080/00268976400100091}}</ref> G<sub>36</sub> shows that one would need to analyse its high resolution ] ] to determine its equilibrium structure. |
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2-Butyne (''dimethylethyne'') forms with ] (''dibutylethyne''), ] (''dipropylethyne'') and ] (''diethylethyne'') a group of symmetric alkynes. |
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==Synthesis== |
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2-Butyne can be synthesized by the ] of ] in a solution of ]ic ].<ref>{{cite book|author1=Victor von Richter |author2=Hans Meerwein|title=Organic Chemistry: Chemistry of the aliphatic series Vol. I: Smith's 3rd American Ed.|year=1916|publisher=P. Blakiston's Sons & Co.|location=Philadelphia|page=89|url=https://books.google.com/books?id=UWlZAAAAYAAJ&q=dimethylacetylene+preparation&pg=PA89}}</ref> |
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==Applications== |
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2-Butyne, along with ], is used to synthesize ] ]s in the ] of ].<ref name=Cyclization>{{cite journal|author1=Reppe, Walter |author2=Kutepow, N |author3=Magin, A |title=Cyclization of Acetylenic Compounds|journal=Angewandte Chemie International Edition in English|year=1969|volume=8|issue=10|pages=727–733|doi=10.1002/anie.196907271}}</ref> |
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==See also== |
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==See also== |
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*] |
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*], a geometric isomer |
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*], a position isomer |
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*] |
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*], a product of 2-butyne ] |
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*] |
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==References== |
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==References== |
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{{reflist}} |
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{{reflist}} |
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{{Alkynes}} |
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{{Alkynes}} |
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{{DEFAULTSORT:Butyne2}} |
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{{hydrocarbon-stub}} |
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{{hydrocarbon-stub}} |
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