Alkyne/Alkene Reactants

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15 Terms

1
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  1. BH3, THF

  2. NaOH, H2O2

Adds syn

anti markovnikov (H → most subbed, OH on least)

Alkyne → alkene →alkane

Alkyne Tautomerizes?

2
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  1. H2, Pd/c

Adds Syn/Cis

(alkyne or alkene → alkane)

3
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  1. OsO4, THF

  2. H2S or NMO

Adds syn/cis

Adds OH to both ends of bond

alkene → alkane

4
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  1. lindlars, H2

  2. MeOH

Adds syn/cis

Alkyne →(Z) Alkene

5
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  1. Br2

  2. H2O

Adds anti/trans

Markovnikov (OH → most subbed, Br → least)

6
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  1. H-Br, DCM

Adds anti/trans

Markovnikov (Br→ most subbed, H→ least

1eq = alkyne→alkene OR alkene→alkane

2eq = alkyne → alkane

7
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  1. X2, CCl4

Adds anti/trans

(becuase of bropoxide intermediate)

X on both sides

8
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  1. Na°NH3

  2. H20, HCl

Adds “anti”

Alkyne →(E)Alkene

9
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H2SO4, H2O

Adds Markovnikov (OH → most subbed, H → least)

carbocation intermediate

10
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H-X

Adds Markovnikov (X → most subbed, H → least)

carbocation intermediate

11
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HgSO4, H2O, H2SO4

Adds Markovnikov (OH→most subbed)

Alkyne→enol→(tautomerization!)→ketone

(acidic hydration of alkyne)

12
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  1. BH(cy)2, THF

  2. NaOH, H2O2

Adds Anti-Markovnikov (O → least subbed)

Alkyne→enol→(tautomerization!)→Aldehyde

(Basic hydration of alkyne)

13
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H-Br, H2O2, hv

Adds E or Z

Markovnikov? (OH → most subbed, Br →least subbed)

14
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CHCl3, KOC(CH3)3

Adds syn (triangle w/ 2 Cl on it)

Alkene → triangle

15
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