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(Alkyl Halide) + (Elemental Lithium/THF)
Organolithium


(Alkyl Halide) + (Elemental Magnesium/THF)
Grignard


(Organolithium x2) + (Copper Halide)
Organocuprate


(Aldehyde) + (1. Organolithium or Grignard 2. H+ wkp)
2° Alcohol


(Ketone) + (1. Organolithium or Grignard 2. H+ wkp)
3° Alcohol


(Ester) + (1. Organolithium or Grignard 2. H+ wkp)
3° Alcohol


(Acid Chloride) + (1. Organolithium or Grignard 2x | 2. H+ wkp)
3° Alcohol


(Epoxide) + (1. Organolithium or Grignard 2. H+ wkp)
Alcohol


(Aldehyde) (1. NaBH4 2. H+ wkp)
1° Alcohol


(Ketone) + (1. NaBH4 2. H+ wkp)
2° Alcohol


(Ester) + (1. LiAlH4 2. H+ wkp)
2x Alcohols


(Carboxylic Acid) + (1. LiAlH4 2. H+ wkp)
2x Alcohols


(1° Alcohol) + (PCC)
Aldehyde


(2° Alcohol) + (PCC)
Ketone


(1° Alcohol) + (H2CrO4 or KMnO4)
Carboxylic Acid


(2° Alcohol) + (H2CrO4 or KMnO4)
Ketone


(Alkene) + (NBS/hv)
Allylic Bromide


(Benzylic Carbon) + (KMnO4, H+, Δ)
Benzoic Acid


(Alcohol) + (SOCl2/pyridine)
Chloroalkane


(Alcohol) + (PBr3)
Bromoalkane


(Aldehyde/Ketone) + (Zn(Hg)/HCl)
Alkane


(Aldehyde/Ketone) + (Hydrazine/KOH)
Alkane


(Alcohol) + (TBS-Cl/Imidazole)
Silyl Ether


(Silyl Ether) + (1. TBu4F 2. H+ wkp)
(Alcohol)


(Diene) + (HBr, -78°C)
1,2 Kinetic Addition of Bromine


(Diene) + (HBr, 40°C)
1,4 Thermodynamic Addition of Bromine


(Diene) + (Dienophile) + (Δ)
Cyclohexene


(Benzene) + (Br2, Δ, FeBr3/AlBr3)
Bromobenzene


(Benzene) + (Cl2, FeCl3/AlCl3
Chlorobenzene


(Benzene) + (HNO3, Δ, H2SO4)
Nitrobenzene


(Benzene) + (SO3, H2SO4)
Benzenesulfonic Acid


(Benzene) + (Alkyl Chloride, AlCl3)
Alkylbenzene


(Benzene) + (Acid Chloride, AlCl3)
Aryl Ketone


(Benzene) + (Anhydride, AlCl3)
Aryl Ketone
