Orgo Reaction Reagents

Sn2 Reaction with Chiral Flip

Strong Nucleophile, Primary or Secondary

E2 Zaitsev anti-elimination

Strong, sterically unhindered base

E2 Hoffman anti-elimination

Strong, sterically Hindered Base

Sn1 racemic substitution

Weak base or strong nucleophile with tertiary leaving group

E1

Weak base or weak nucleophile. Secondary or tertiary

Tosylation

TsCl, Pyridine

Hydrohalogenation (Markovnikov)

HX

Hydrohalogenation (anti-Markovnikov)

HBr, ROOR

Acid-catalyzed hydration and oxymercuration-demercuration. Markovnikov, protection from rearrangements.

1) Hg(OAc)2, H2O. 2) NaBH4

Hydroboration-Oxidation. Anti-Markovnikov, anti addition of hydroxyl group

1) BH3, THF. 2) H2O2, NaOH

Hydrogenation (syn)

H2, (Pt, Pd, or Ni)

Bromination (anti)

Br2

Halohydrin Formation (anti)

Br2, H2O

anti dihydroxylation

1) McPBA. 2)H3O+

Syn dihydroxylation

1) OsO4. 2) NaHSO3, H2O OR 1) KMnO4, NaOH, cold

Ozonolysis

1) O3. 2) DMS or Zn/H2O

Elimination on an alkyne

1) Excess NaNH2. 2) H2O

Acid-Catalyzed Hydration

HgSO4, H2SO4, H2O

Hydroboration-oxidation

1) R2BH. 2) H2O2, NaOH

Ozonolysis of an Alkyne

1) O3. 2) H2O

Alkylation

1) NaNH2. 2) RX

Dissolving metal reduction (anti)

Na, NH3(l)

Hydrogenation with a poisoned catalyst (syn)

H2, Lindlar’s catalyst