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Note - this sheet is not meant to be comprehensive. Your course may provide additional material, or may not cover some of the reactions shown here. Your course instructor is the final authority.
+4
Notes: to keep things relatively simple, several common functional groups (amines, epoxides, ethers, and many more) have been omitted. All alkyl halides are drawn as chlorides ("Cl"). For Br and I, the corresponding reagent containing those atoms should be employed. Oxidation here is defined as: loss of a CH bond or gain of a CO bond (or equivalent) Reduction here is defined as: gain of a CH bond or loss of a CO bond (or equivalent)
H2O, acid ROH, acid O O Cl R NH3 or other amine O H2N Amide H2O, acid R P2O5 H2O, acid O C R RO Ester R
+2
LiAlH4
HO
Carboxylic acid
Acid halide
Nitrile
R E D U C T I O N 0
O X I D A T I O N
H2CrO4 or KMnO4
DIBAL
H2O, H2SO4 or HgSO4, H2O, H2SO4 NaNH2 NaNH2 R Alkyne H2, Lindlar's catalyst HCl Cl Cl R Dihalide (Geminal) R Ketone O RMgCl or RLi
O3, Zn (or DMS) H2SO4, heat H2O, H2SO4 or Hg(OAc)2, H2O, then NaBH4 Cl R Alkyl halide (Secondary) NaOH (SN2) HCl
NaBH4 or LiAlH4
PCC or H2CrO4
HO
-2
Cl PCl3 or SOCl2
OH R Alcohol (Secondary)
OH R Alcohol (Tertiary)
Alcohol (Primary)
Pd/C H2
Cl2, light
Cl2, light R Alkanes Omissions, Mistakes, Suggestions? james@writechem.com This sheet copyright 2011, James A. Ashenhurst masterorganicchemistry.com R