Reactants, Conditions, and Catalysts for Alkenes and Alkynes

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Last updated 5:29 AM on 4/16/26
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21 Terms

1
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hydrohalogenation

HBr or HCl or HI

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acid-catalyzed hydration

H2O, H2SO4

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acid-catalyzed hydration w/alcohol solvent

ROH, HCl (catalyst)

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addition of bromine and chlorine

X2, CH2Cl2

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addition of HOCl and HOBr

X2, H2O

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oxymercuation-reduction

  1. Hg(OAc)2, THF/H2O

  2. NaBH4, H2O

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hydroboration-oxidation of alkenes

  1. BH3, THF

  2. H2O2, NaOH, H2O

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oxidation with OsO4

OsO4, H2O, H2O2

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ozonolysis

  1. O3

  2. (CH3)2S

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catalytic reduction

H2, catalyst (Pd or Pt or Ni)

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alkenes to alkynes

  1. X2, CH2Cl2

  2. dehydrohalogenation

    1. NaNH2 (gives terminal alkyne), NH3

    2. H2O

or

KOH (gives internal alkyne), EtOH

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alkylation/ nucleophilic substitution /addition of more carbons to alkynes

  1. NaNH2, NH3

  2. RX

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hydroboration-oxidation of alkynes

  1. (sia)2BH, THF

  2. H2O2, NaOH

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acid-catalyzed hydration of alkynes

HgSO4, H2SO4, H2O

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catalytic reduction from alkynes to alkanes

H2, catalyst (Pd or Pt or Ni)

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catalytic reduction from alkynes to cis-alkenes

H2, Lindlar’s catalyst

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metal reduction from alkenes to trans-alkenes

Na°, NH3(l)

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SN2

rate = k[RX][Nu-]

  • increases with decreasing electronegativity

  • uses strong nucleophiles

  • polar aprotic solvent

  • inversion of configuration

  • used in 1o and 2o alkyl halides

    • majority in 1o alkyl halides when using strong nucleophile and base

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SN1

rate = k[RX]

  • uses weak nucleophiles

  • polar protic solvent

  • inversion and retention of configuration

  • used in 2o and 3o alkyl halides

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E1

rate = k[RX]

  • only occurs for weak bases/nucleophiles

  • favors the more stabilized product

  • used in 2o and 3o alkyl halides

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E2

rate = k[RX][base]

  • used in 2o and 3o alkyl halides

  • stereospecfic

    • β-hydrogen and leaving group must be anti and co-planar

  • bulky (non-nucleophilic) bases give the Hoffman product