Alkenes & Alkanes

Alkene + HX

Markovnikov addition; H adds to less substituted C, X to more substituted C

Alkene + HBr + ROOR

Anti-Markovnikov addition, Br adds to less substituted carbon

Alkene + H₃O⁺

Markovnikov hydration, OH to more substituted carbon

Alkene + 1) Hg(OAc)₂, H₂O 2) NaBH₄

Markovnikov hydration, NO rearrangements (oxymercuration-demercuration)

Alkene + 1) BH₃·THF 2) H₂O₂, NaOH

Anti-Markovnikov hydration; OH to less substituted carbon

Alkene + Br₂

Anti addition, forms vicinal dibromide (two Br on adjacent carbons)

Alkene + Br₂, H₂O

Forms halohydrin, OH on more substituted carbon

Alkene + OsO₄ or cold KMnO₄

Syn dihydroxylation, forms cis diol (OH/OH same side)

Alkene + 1) RCO₃H 2) H₃O⁺ Epoxidation then ring opening

anti diol (OH opposite sides)

Alkene + O₃, DMS Ozonolysis

splits double bond into aldehydes/ketones

Alkene + H₂, Pt Hydrogenation

adds H/H

Alkyne + HX (1 equiv)

Forms vinyl halide (alkene with X)

Alkyne + HX (excess)

Forms geminal dihalide (two X on same carbon)

Alkyne + HgSO₄, H₂SO₄, H₂O Markovnikov hydration

forms ketone

Alkyne + 1) R₂BH 2) H₂O₂, NaOH Anti-Markovnikov hydration

forms aldehyde (terminal alkyne)

Alkyne + X₂ (1 equiv)

Forms dihaloalkene

Alkyne + X₂ (excess)

Forms tetrahalide (4 halogens added)

Alkyne + O₃, H₂O Ozonolysis

splits into carboxylic acids (terminal gives CO₂ + acid)

Alkyne + H₂, Pt Fully hydrogenated

alkane

Alkyne + H₂, Lindlar catalyst Partial hydrogenation

forms cis alkene (syn addition)

Alkyne + Na, NH₃ (liq) Partial reduction

forms trans alkene (anti addition)

Terminal alkyne + NaNH₂ Deprotonation

forms acetylide anion (strong nucleophile)

Acetylide anion + R–X SN2 reaction

forms new C–C bond (chain extension)