2410 Exam 2 Reagent Flashcards

Acid-catalyzed hydration (alkene)

H2O, H2SO4 (H3O+)

Oxymercuration-demercuration (alkene)

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

Hydroboration-oxidation (alkene)

1) BH3·THF 2) H2O2, NaOH, H2O

Halogenation (alkene)

X2 in CCl4 or CH2Cl2

Halohydrin formation (alkene)

X2 (Cl2 or Br2), H2O

Catalytic hydrogenation (alkene)

H2 with Pt, Pd, or Ni

Epoxidation (alkene)

RCO3H (usually mCPBA)

Anti dihydroxylation (alkene)

1) RCO3H (mCPBA) 2) H3O+

Syn dihydroxylation (alkene)

1) OsO4 2) NaHSO3 — or cold, dilute KMnO4, NaOH

Ozonolysis / oxidative cleavage (alkene)

1) O3 2) DMS (or Zn/H2O)

Preparation of alkynes

1) Excess NaNH2, NH3 2) H2O

Catalytic hydrogenation (alkyne)

2 eq H2 with Pt, Pd, or Ni

Lindlar hydrogenation (alkyne)

H2, Lindlar's catalyst (poisoned Pd)

Dissolving metal reduction (alkyne)

Na, NH3 (l)

Hydrohalogenation (alkyne)

HX (HBr + ROOR for anti-Markovnikov)

Hydration (alkyne)

H2O, H2SO4, HgSO4

Hydroboration-oxidation (alkyne)

1) 9-BBN (or BH3·THF) 2) H2O2, NaOH

Halogenation (alkyne)

X2 in CCl4 or CH2Cl2

Ozonolysis / oxidative cleavage (alkyne)

1) O3 2) H2O

Alkylation (terminal alkyne)

1) NaNH2 2) RX (methyl or 1°) — stepwise for each R