Organic Chemistry 1 Alkene & Alkyne Reactions and Reagents

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23 Terms

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Hydrohalogenation (Markovnikov)

HBr

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Hydrohalogenation (Anti-markovnikov)

HBr/ROOR

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Oxymercuration/Demurcuration

  1. Hg(OAc)2, H2O

  2. NaBH4

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Hydroboration/oxidation

  1. BH3 THF

  2. H2O2, NaOH

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Hydrogenation

H2/Metal

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Halogenation

X2/CCl4

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Halohydrin

X2/H2O

  • Halogen is on less substituted C

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Epoxidation

RCO3H (McPBA)

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Anti-Dihydroxylation

  1. McPBA

  2. H3O+

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Acid-Catalyzed Hydration

H2O4(dil) or H3O+

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Syn-Dihydroxylation

  1. OSO4

  2. NaHSO4

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Ozonolysis (Alkenes)

  1. O3

  2. DMS

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Alkyne Reduction: H2/Metal

Alkane

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Alkyne Reduction: H2/Lindlar’s

Cis-Alkene

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Alkyne Reduction: Na/NH3 (l)

Trans-Alkene

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Acid-Catalyzed Tautomerization

HgSO4/H3O+

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Base-Catalyzed Tautomerization

  1. RBH3 * THF

  2. H2O2, NaOH

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Halogenation (Alkyne)

  • VICINAL

xs X2/CCl4

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Hydrohalogenation (Alkyne)

  • GEMINAL

xs HX

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Ozonolysis (Alkyne)

  1. O3

  2. H2O

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Alkylation (Adding Carbons)

NaNH2

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Making an Alkyne From Geminal/Vicinal LG (alkane)

xs NaNH2

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Making an Alkene from OH

H2SO4 (conc.) / Heat