• anti stereochemistry
• bromonium ion
• carbene, R₂C
• chain-growth polymer
• epoxide
• glycol
• halohydrin
• hydroboration
• hydrogenated
• hydroxylation
• monomer
• oxidation
• oxirane
• oxymercuration–demercuration
• ozonide
• polymer
• reduction
• Simmons–Smith reaction
• stereospecific
• syn stereochemistry

Summary of Reactions

No stereochemistry is implied unless specifically indicated with wedged, solid, and dashed lines.

• Addition reactions of alkenes
• Addition of HCl, HBr, and HI (Section 7.7 and Section 7.8); Markovnikov regiochemistry occurs, with H adding to the less highly substituted alkene carbon and halogen adding to the more highly substituted carbon.

• Addition of halogens Cl₂ and Br₂ (Section 8.2); Anti addition is observed through a halonium ion intermediate.

• Halohydrin formation (Section 8.3); Markovnikov regiochemistry and anti stereochemistry occur.

• Addition of water by oxymercuration–demercuration (Section 8.4); Markovnikov regiochemistry occurs.

• Addition of water by hydroboration–oxidation (Section 8.5) Non-Markovnikov syn addition occurs.

• Catalytic hydrogenation (Section 8.6) Syn addition occurs.

• Epoxidation with a peroxyacid (Section 8.7) Syn addition occurs.

• Hydroxylation with OsO4 (Section 8.7) Syn addition occurs.

• Addition of carbenes to yield cyclopropanes (Section 8.9)
• Dichlorocarbene addition

• Simmons–Smith reaction

• Hydroxylation by acid-catalyzed epoxide hydrolysis (Section 8.7) Anti stereochemistry occurs.

• Oxidative cleavage of alkenes (Section 8.8)
• Reaction with ozone followed by zinc in acetic acid

• Reaction with KMnO4 in acidic solution

• Cleavage of 1,2-diols (Section 8.8)