alkenes, alkynes, and radicals

hydrohalogenation; markonikov (potentially chiral)

hydrohalogenation; anti-markovnikov (potentially chiral)

acid catalyzed hydration; may be chiral; may have rearrangement

acid catalyzed hydration; may be chiral; may have rearrangement

oxymercuration-demercuration; NO rearrangement

hydroboration-oxidation; OH syn addition in anti-markonikov position to the hydrogen

hydroboration-oxidation; anti-markovnikov OH addition

catalytic hydrogenation; may form chiral centers (syn)

catalytic hydrogenation; may form chiral centers (syn), unless MESO

halogenation; anti; only with Cl2 and Br2

halohydrin formation

peroxyacid reaction

anti dihydroxylation; creates a trans diol

syn dihydroxylation

syn dihydroxylation

ozonolysis

preparation of a terminal alkyne

reduction of alkyne (cis)

reduction of alkynes / dissolving metal reduction

anti-markonikov hydrohalogenation

only with HBr; hydrohalogenation of terminal alkynes

hydration (ketone)

halogenation (excess)

halogenation (one equ)

ozonolysis

terminal ozonolysis

terminal alkylation

halogenation (indiscriminate regioselectivity)

halogenation with regioselectivity

allylic halogenation

allylic halogenation

autooxidation

autooxidation of an ether

synthetic utility of halogenation