Reactions of Alkynes

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10 Terms

1
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H2, Pd/C (excess)

H2, Lindlars

alkane

cis/syn additon

2
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Na or Li, NH3 (liquid)

alkane

anti-trans

3
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2 equiv HX

geminal dihalide

markovnikov

4
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geminal

on same sides of the same carbon bond

5
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trans

opposite sides across 2 carbons

6
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cis

same sides across 2 carbons

7
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2 equiv X2

tetrahalide

2 halogens add anti of triple bond, then again

4 halogens total

8
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1) O3 2) H2O or KMnO4 (hot, conc.

COOH formed on internal alkyne

CO2 formed on terminal alkyne

9
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H2SO4, H2O, HgSO4

enol tautomerization to ketone

markovnikov

10
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1) BH3 or Sia2BH 2) H2O2, OH–

anti-mark

tautomerization to aldehyde

(terminal= aldehyde, internal= ketone)