Addition Reactions of Alkenes

Alkene + HBr ROOR

Hydrohalogenation Anti-markovnikov

Alkene + Hx

Hydrohalogenation markovnikov

Alkene + 1) O3 2) DMS

Ozonolysis

Alkene + 1) OsO4 2)NaHSO3 H2O

Syn dihydroxylation syn addition

+ EN

Alkene + 1) RCO3H 2) H30+

Anti dihydroxylation anti addition

+ EN

Alkene + Br2, H20

Halohydrin formation anti addition

+ EN

Alkene + Br2

Bromination anti addition

+ EN

Alkene + H2 Pt

Hydrogenation syn addition

Alkene + 1) BH3 THF 2)H2O2, NaOH

Hydroboration-oxidation, anti markovnikov, syn addition

+ EN

Alkene + 1) Hg(OAc)2 H2O 2) NaBH4

oxymercuration-demercuration markovnikov

Alkene + H30⁺

Acid-catalyzed hydration markovnikov addition

Alkyne + H₂, Pd, Pt or Ni (metal catalyst)

alkyne hydrogenation

Alkyne + Na (s) or Li (s) (metal), NH₃(l)

dissolving metal reduction, trans, does not affect double bonds

Alkyne + H₂, Lindlar’s catalyst

Hydrogenation with a poisoned catalyst, cis

Alkane + 1) excess NaNH₂ 2)H₂O

Elimination (preparation of an alkyne)

Alkyne + 1) NaNH₂ 2) RX

Alkylation

Alkyne + HX

Hydrohalogenation (one equivalent), markovnikov

Tertiary substrate, Strong bulky base, weak nucleophile (DBN, DBU, ^-OTBu)

E2 reaction

Primary substrate, Strong bulky base, weak nucleophile (DBN, DBU, ^-OTBu)

E2 reaction

Secondary substrate, Strong bulky base, weak nucleophile (DBN, DBU, ^-OTBu)

E2 reaction

Primary substrate, Strong base, Strong Nucleophile (HO^-, MeO^-, EtO^-)

Sn2 major, E2 minor

Secondary substrate, Strong base, Strong Nucleophile (HO^-, MeO^-, EtO^-)

E2 major, Sn2 minor

Tertiary substrate, Strong base, Strong Nucleophile (HO^-, MeO^-, EtO^-)

E2 reaction

Primary substrate, Weak base, Strong nucleophile (I^- Br^-, Cl^-, RS^-, HS^-, RSH, H₂S, ^-CN, N₃₎

Sn2 reaction

Secondary substrate, Weak base, Strong nucleophile (I^- Br^-, Cl^-, RS^-, HS^-, RSH, H₂S, ^-CN, N₃₎

Sn2 reaction

Tertiary substrate, Weak base, Strong nucleophile (I^- Br^-, Cl^-, RS^-, HS^-, RSH, H₂S, ^-CN, N₃₎

Sn1 reaction

Tertiary substrate, weak base, weak nucleophile (H₂O, MeOH, EtOH), temp. is not mentioned

Sn1 and E1 major products

Tertiary substrate, weak base, weak nucleophile (H₂O, MeOH, EtOH), hot temperature

E1 reaction

Tertiary substrate, weak base, weak nucleophile (H₂O, MeOH, EtOH), room temperature

Sn1 reaction

Primary substrate, weak base, weak nucleophile (H₂O, MeOH, EtOH), temp. is not mentioned

no reaction

Secondary substrate, weak base, weak nucleophile (H₂O, MeOH, EtOH), temp. is not mentioned

no reaction