Alkyne Reactions

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11 Terms

1
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H2, Lindlar’s catalyst

  • Internal alkyne → alkene

  • Creates a cis alkene


<ul><li><p>Internal alkyne → alkene</p></li></ul><ul><li><p>Creates a cis alkene</p></li></ul><p></p>
2
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H2, Pt

  • Internal alkyne → alkane


<ul><li><p>Internal alkyne → alkane</p></li></ul><p></p>
3
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Na, NH3 (l)

  • Internal alkyne → alkene

  • Creates a trans alkene


<ul><li><p>Internal alkyne → alkene</p></li><li><p>Creates a trans alkene</p></li></ul><p></p>
4
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1) xs NaNH3, 2) H2O

  • Germinal / vicinal alkane → terminal alkyne


<ul><li><p>Germinal / vicinal alkane → terminal alkyne</p></li></ul><p></p>
5
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xs HX

  • terminal alkyne → germinal alkane


<ul><li><p>terminal alkyne → germinal alkane</p></li></ul><p></p>
6
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HX

  • terminal alkyne → alkene

  • Markovnikov addition of a halogen


<ul><li><p>terminal alkyne → alkene</p></li><li><p>Markovnikov addition of a halogen</p></li></ul><p></p>
7
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HgSO4, H2SO4, H2O

  • Acid-catalyzed Enol-Keto tautomerization

  • The pi bond in an enol acts as an acid to make a ketone


<ul><li><p>Acid-catalyzed Enol-Keto tautomerization</p></li><li><p>The pi bond in an enol acts as an acid to make a ketone</p></li></ul><p></p>
8
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1) R2BH, 2)H2O2, NaOH

  • Base-catalyzed Enol-Aldehyde tautomerization

  • The pi bond in an enol acts as a base to make an aldehyde



<ul><li><p>Base-catalyzed Enol-Aldehyde tautomerization</p></li><li><p>The pi bond in an enol acts as a base to make an aldehyde</p></li></ul><p></p><p></p>
9
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X2 (one equvi.), CCl4

  • terminal alkyne → alkene w/ two halogens across the pi bond


<ul><li><p>terminal alkyne → alkene w/ two halogens across the pi bond</p></li></ul><p></p>
10
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xs X2, CCl4

  • terminal alkyne → alkane w/ 4 halogens across the original alkyne


<ul><li><p>terminal alkyne → alkane w/ 4 halogens across the original alkyne</p></li></ul><p></p>
11
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1) O3, 2) H2O

  • terminal alkyne → carboxylic acid + CO2

  • If its an internal alkyne, two carboxylic acids are made


<ul><li><p>terminal alkyne → carboxylic acid + CO<sub>2</sub> </p></li><li><p>If its an internal alkyne, two carboxylic acids are made</p></li></ul><p></p>