Orgo Reagent Table

H₂, Pd/C (or Pt, Ni)

cleaves C=C

adds H, H

syn stereochemistry

X₂ (Cl₂/Br₂)

inert solvent (CH₂Cl₂, CCl₄)

adds X, X

anti stereochemistry

X₂ then H₂O

adds X, OH

Markovnikov regiochemistry

anti stereochemistry

X₂ then ROH

adds X, OR

Markovnikov regiochemistry

anti stereochemistry

HX (HBr/HCl/HI)

adds H, X

Markovnikov regiochemistry

mixture stereochemistry

HBr + ROOR (peroxides)

adds H, Br

anti-Markovnikov regiochemistry

only works for Br (no HCl or HI)

Hg(OAc)₂/H₂O, then NaBH₄

adds H, OH

Markovnikov regiochemistry

anti stereochemistry

NO carbocation rearrangement

Hg(OAc)₂ + aq. HOAc

adds H, OH

Markovnikov regiochemistry

makes enol, ends up as "methyl ketone"

NO carbocation rearrangement

BH₃•THF then H₂O₂, NaOH

adds H, OH

anti-Markovnikov regiochemistry

syn regiochemistry

H₂SO₄ cat. then H₂O

adds H, OH

Markovnikov regiochemistry

not stereospecific (racemic)

rearrangements CAN occur

O₃, then H₂O₂ (oxidative)

cleaves C=C

O₃, then (CH₃)₂S (DMS) or Zn/H₂O (reductive)

cleaves C=C