Reagents
Common organic chemistry reagents: what each one does, when to use it and what to watch out for.
- 1. R₂BH 2. H₂O₂/OH⁻
- BH₃·THF; H₂O₂/NaOH
- Br₂
- Br₂, hν
- Br₂/FeBr₃
- Br₂/H⁺
- Br₂/H₂O
- Br₂/OH⁻
- Cl₂
- Cl₂, hν
- Cl₂/FeCl₃
- CuBr
- CuCl
- CuCN
- Dess–Martin (DMP)
- DIBAL-H
- Excess H₂/Pd
- Fe/HCl
- H₂, Pt
- H₂/Lindlar
- H₂/Pd-BaSO₄
- H₂/Pd-C
- H₂CrO₄ / Jones
- H₂O
- H₂O, H₂SO₄
- H₂O, heat
- H₂SO₄, heat
- H₃O⁺
- H₃O⁺, heat
- H₃PO₂
- HBr
- HBr, ROOR
- HCl
- HCN/KCN
- Hg(OAc)₂/H₂O; NaBH₄
- HgSO₄, H₂SO₄, H₂O
- HI
- HNO₃/H₂SO₄
- HOCH₂CH₂OH, H⁺
- KMnO₄, hot
- KOtBu
- LDA then R–X
- LDA, THF, −78 °C
- LiAlH₄ (LAH)
- mCPBA
- MsCl, Et₃N
- Na/NH₃(l)
- Na₂Cr₂O₇/H₂SO₄
- NaBH₄
- NaCN
- NaH
- NaI / acetone
- NaN₃
- NaNH₂
- NaNH₂ + terminal alkyne
- NaNH₂ then R–X
- NaNO₂/HCl, 0–5 °C
- NaOEt/EtOH
- NaOH
- NaOH/H₂O
- NaOH/OH⁻
- NaOMe / MeOH
- NBS, hν
- NH₂NH₂
- NH₂NH₂, KOH, heat
- NH₂OH
- O₃, then H₂O₂
- O₃, then Me₂S or Zn
- OH⁻, heat
- OsO₄
- PBr₃
- PCC
- Ph₃P=CHR
- R–Cl/AlCl₃
- R₂CuLi
- R₂NH, H⁺
- RCOCl/AlCl₃
- RLi
- RMgX
- RMgX + CO₂; H₃O⁺
- RMgX + epoxide
- RMgX, then H₃O⁺
- RMgX; H₃O⁺
- RNH₂
- RNH₂, H⁺
- ROH
- ROH/H⁺
- Sn/HCl
- SO₃/H₂SO₄
- SOCl₂
- Swern: DMSO, (COCl)₂, Et₃N
- TsCl, pyridine
- Zn(Hg), HCl