chapter 13 electrophilic addition to pi bonds

epoxidation using peroxyacid reagents?

MCPBA

NaHCO3, H2O

epoxidation stereochemistry?

potential for a mix of isomers due to the addition happening on top and on bottom of the alkene

cyclopropination using carbenes reagents?

CH2N2

hv (ultraviolet light)

cyclopropination stereochemistry?

potential for a mix of isomers due to the addition happening on top and on bottom of the alkene

synthesis of 1,2-dihalides reagents?

Br2 (desired halide)

CCl4

1,2-diahlide stereochemistry?

anti addition (mix of enantiomers)

Halohydrin formation reagents?

Br2 (desired halogen)

H2O

oxymercuration/reduction reagents?

Hg(OAc)2, H2O THF

BH4, ethanol

oxymercuration stereo/regiochem

anti addition

OH adds to the more substituted carbon without carbocation rearrangement

hydroboration/oxidation reagents?

BH3 THF

H2O2, NaOH, H2O

hydroboration stereo/regiochem

OH adds to the less substituted carbon

syn addition

oxymercuration alkynes reagents

Hg(OAc)2, H2O

acetic acid

oxymercuration alkynes mechanism

add a ketone where the alkyne is

hydroboration alkynes reagents

disiamylborane Sia₂BH

NaOH, H2O2