Addition of Alkenes

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14 Terms

1
New cards

List reagents, regioselectivity, and stereoselectivity of hydrogenation

  • Reagents: H2 or D2 + Metal (Pd/C, Pt, Rainey Ni)

  • Regio: N/A

  • Stereo: syn


2
New cards

List reagents, regioselectivity, and stereoselectivity of electrophilic addition

  • Reagents: H-X, X = halogen

  • Stereo: N/A

  • Regio: Mark


3
New cards

List reagents, regioselectivity, and stereoselectivity of mark of H-OH

  • Reagents: cat. H2SO4 or TSOH and H2O

  • Stereo: N/A

  • Regio: Mark


4
New cards

List reagents, regioselectivity, and stereoselectivity of addition of X2

  • Reagents: X2 and CCl4 (nonpolar, aprotic)

  • Stereo: anti

  • Regio: N/A


5
New cards

List reagents, regioselectivity, and stereoselectivity of hydrohalogenation

  • Reagents: X2 and H2O (polar, protic)

  • Stereo: anti

  • Regio: mark


6
New cards

List reagents, regioselectivity, and stereoselectivity of oxymercuration-demercuration

  • Reagents: 1) Hg(OAc)2, H2O 2) NaBH4, H2O, NaOH

  • Stereo: 1) anti 2) N/A

  • Regio: mark


7
New cards

List reagents, regioselectivity, and stereoselectivity of hydroboration-oxidation

  • Reagents: 1) BH3 and THF 2) H2O2, NaOH

  • Stereo: syn

  • Regio: anti-mark


8
New cards

List reagents, regioselectivity, and stereoselectivity of epoxidation-racemic

  • Reagents: mCPBA or X2 and H2O → strong base (NH2)

  • Stereo: syn

  • Regio: N/A


9
New cards

List reagents, regioselectivity, and stereoselectivity of epoxidation-single enantiomer

  • Reagents: Jacobsen’s catalyst, NaOCl (bleach)

  • Stereo: syn?

  • Regio: N/A


10
New cards

List reagents, regioselectivity, and stereoselectivity of diol synthesis-epoxide opening

  • Reagents: H3O+ (H2O + H+)

  • Stereo: anti

  • Regio: N/A


11
New cards

List reagents, regioselectivity, and stereoselectivity of diol synthesis-dihydroxylation

  • Reagents: catalytic OSO4 and H2O2

  • Stereo: syn

  • Regio: N/A


12
New cards

List reagents of ozonolysis-reductive workup and what happens

  • Reagents: O3 at -78 C and Me2S or NaHSO3

  • Break DB replace with C=O (carbonyl)

  • Retain all substituents of alkene even H


13
New cards

List reagents of ozonolysis-oxidative workup and what happens

  • Reagents: O3 at -78 C and H2O2

  • carboxylic acid


14
New cards

List reagents, regioselectivity, and stereoselectivity of anti-mark add. of H-Br

  • Reagents: ROOR and HBr

  • Stereo: N/A

  • Regio: anti-mark