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H2, Pd-C
alkyne/alkene —> alkane (syn)
Na, NH3
alkyne —> alkene (trans)
H2, Lindlar catalyst
alkyne —> alkene (syn)
LiAlH4 or NaBH4
carbonyl —> OH
mCPBA
1) alkene —> epoxide (achiral —> achiral/racemic mixture)
2) epoxide —> 2 OH groups (anti)
OsO4/NMO
or KMnO4/OH-
2 OH groups added to alkene (syn)
1) O3
2) DMS or Zn
cleavage, two groups w C=O
PCC
primary alcohol —> aldehyde (in presence of water, undergoes further oxidation)
CrO3 and Na2Cr2O7
primary alcohol —> carboxylic acid
Na2Cr2O7
(PCC or CrO3 possibly)
secondary alcohol —> ketone (C=O)