reactions + reagents

H-X

hydrohalogenation,

addition of H,X

H-Br + ROOR

hydrohalogenation,

addition H, Br

H2O + H+ + H3O+ or H2SO4

ALKENE acid - catalyzed hydration

addition of H, OH

Hg(OAc)2, H2O + NaBH4

oxymercuration-demercuration

addition of H, OH

BH3, THF + H2O2, NaOH

ALKENE + ALKYNE hydroboration-oxidation

addition H, OH

syn

H2 + cat

ALKENE + ALKYNE catalytic hydrogenation

addition of H, H

syn

Br2 or Cl2; sometimes with CCl4 or CBr4

ALKYNE halogenation

addition of X2 or X4

Br2 or Cl2 + H2O or ROH

halohydrin

addition of X, OH

ANTI

MCPBA, RCO3H

epoxide

addition of epoxide

OsO4, NaHSO3, H2O or KMnO4, NaOH, cold

syn dihydroxylation

addition of OH, OH

syn

O3, DMS

ALKENE oxidative cleavage

addition of C=O bonds

H2SO4, H2O, HgSO4

ALKYNE acid-catalyzed hydration

addition of H, OH

Br2 or Cl2

ALKENE halogenation

addition of X2

ANTI

O3, H2O

ALKYNE oxidative cleavage

addition of C=O bonds

2 NaNH2, NH3, maybe H2O

making alkynes

lindler’s catalyst

partial catalytic hydrohalogenation

addition of H,H

partial reduction to alkene

Na(s), NH3 (s)

dissolving metal reduction

addition of H,H

partial reduction to alkene

NaNH2, R-X

alkylation of terminal alkynes

addition of R chain

LiALH4, NaBH4, RMgX (grignard’s)

reduction of alcohols

H2CrO4, NaCrO7, H2SO4, H2O (jones)

oxidation of alcohols

NBS

allylic bromination

heat and light (X2)

radical halogenation of alkanes

THF

weak nucleophile, weak base

E1/SN1

LDA

strong nucelophile, strong base

E2/SN2

DMS

strong nucleophile, strong base

E2/SN2

tBuOK

strong nucleophile, strong base

E2/SN2

NaSR

strong nucelophile, weak base

E2/SN2

RCO3H + H3O+

anti-dihydroxylation

addition of OH, OH

ANTI